Gangland Wire

Gary Jenkins: Mafia Detective
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  • Gangland Wire

    The Life of a NYPD Cop

    25.05.2026
    Retired Kansas City Police Intelligence Unit detective Gary Jenkins sits down with former NYPD officer Jimmy Dennedy and NYC Brooklyn prosecutor Michael Vecchione for a gripping discussion on violent crime, justice, and redemption.

    Jimmy recounts the shocking murder of NYPD officers Rocco Laurie and Gregory Foster by the Black Liberation Army, while Michael reveals the challenges of prosecuting those responsible.

    The conversation then shifts to something unexpected—redemption. After retiring, Jimmy began working in prison ministry, where he witnessed firsthand how even hardened criminals, including mobsters, can change their lives.

    This episode dives deep into:

    The reality of cop killings in New York City

    The struggle to prosecute violent offenders

    Inside stories from mob cases

    Redemption and transformation inside prisons

    Get the book Hard Guys Cry.

    If you’re interested in true crime, mafia history, and real law enforcement stories, this is an episode you don’t want to miss.

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    [0:00] Hey, all you wiretappers, good to be back here in studio, Gangland Wire. This is Gary Jenkins, retired Kansas City Police Intelligence Unit detective and now turned podcaster. And I have another retired cop here on the show, Jimmy Dennedy. Jimmy, I tell you what, I had it down, Dennedy, like Kennedy. And our friend who’s been on here several times, Michael Vecchione. Welcome, Michael. Welcome, Jimmy. Thank you very much for having us, Gary. Thank you. All right. Michael has several books out there. He’s, he’s prosecuted the mob. That’s how I got onto him. He prosecuted the, he had something to do with the mob cops, Louis Eppolito. And I can’t remember exactly now. I should have made a note on that, Michael. What was the name of that book?

    [0:48] The name of the book? Friends of the Family. Friends of the Family. Is that those two New York PD coppers that were in the pay of? Louis Eppolito and Louis Eppolito was one of the cops. And you know what, Gary? during the, when Jimmy, when you talk to Jimmy, Jimmy has a kind of a, an odd situation regarding Louie Eppolito. And, and it’s a good story. I think he should tell you, tell your listeners. All right. Great. We look forward to that, Jimmy and Jimmy Denity, who was a New York city policeman. And he has a book, tough dies to cry. Hard guys cry. Let me do that over again. Yeah. I said, I left, I had it written down here and he had Jimmy Denity is here with us. He is a retired New York City copper, and he has a book, Hard Guy’s Cry. So welcome, Jimmy.

    [1:34] Good morning. Thank you very much for having me. All right, Michael, you and Jimmy, did you guys work together a little bit on the job? Did you know each other back then? Yeah, we certainly did. We’ve probably known each other now for maybe 45 or more years. I got to know Jimmy because I got assigned a case involving, unfortunately, the death, the murder of two New York City police officers who were assigned to Jimmy’s precinct at the time in Bed-Stuy. And it was a case that had been tried twice before I got it. And there were hung juries in both of the cases. And the DA at that point was going to just simply decide to not prosecute it anymore. And the head of the policeman’s union went to the DA, the district attorney, and said, listen, just give it one more shot. So I was at the time the head of a group called the Major Offense Bureau in the Brooklyn DA’s office. And I got, I’ll never forget this. I was sitting at my desk and the boss of the unit, the bureau that I was part of, came into my office and said, come with me. We’ll go to see the DA.

    [2:41] I didn’t know. I thought maybe I was in trouble for some reason, but I sat down and he said, listen, I want to give you one more shot. I want to take this case to trial one more time and you are the guy that we want to do it. So I was happy to do it. I tried a lot of cases by that point. And, and the best part of the whole situation, Gary is I met Jimmy Danity. That was, he, we became fast friends and I got to tell you a little funny story. He had been involved in the two other trials.

    [3:11] But when he sat down with me, the first thing he said to me was, or one of the first things was, do you eat lunch? I said, yeah, of course I eat lunch. Why? He said, the guy that tried the case before you and the one before him, they didn’t eat lunch. And by the time the afternoon came, their energy was all waned, had waned. And he said, so here’s what I’m going to do. I’m going to have lunch on your desk every time you come back for the lunch break from the trial. And he did. There was a sandwich waiting for me every day when I came back, and he is the guy that brought it to me. But before the trial, we went out. Me, Jimmy, and detective from the Homicide Bureau, who was assigned to the case.

    [3:57] Tony Martin, went out to the scene. And again, another one of these scenes, which I’ll never forget. The scene was in the middle of Bed-Stuy on Troop Avenue. Jimmy, that was the, yeah.

    [4:10] Willoughby and Troop. Willoughby and Troop. So we’re on the street and the three of us are standing there right on the sidewalk. And we look around and I said to Tony, did you hit every one of these buildings looking for witnesses? Because there was a problem with the case with the witnesses. One had died in a very strange way. And so he looked around I don’t know if you remember this, Jimmy And he pointed to a building Diagonally across from the spot Where the two cops were shot And he said, Mike We never went into that building, And Jimmy and Tony went into the building, canvassed it and came up with two new witnesses. And so it was a wonderful experience working with Jimmy. He was a hard worker. He really was tied to this case in the sense that these guys were his friends. They were two guys who were gunned down for really no reason by a member of the Black Liberation Army at the time who was part of the Attica riots here in New York. He was actually one of the guys who started the Attica riots in New York. And he was out and he was with another guy. And we believe that they were going to meet another one of their fellow.

    [5:27] I don’t want to call them gang members, to set up a robbery. And that’s why they were in Brooklyn. And the case had so many ups and downs and twists and turns. And it was something which I obviously will never forget. But the best part about it, I’ll repeat myself, is that I met Jimmy Denity. And he and I have been friends from that point on until today. And so let me just get to the book because Hard Guy’s Cry to me was a labor of love. It really was. I got a call one afternoon and I’m sitting out on my deck and Jimmy calls me and we just got to talking and he asked me about doing a book about his life and his story. And I said, it’s great. There are lots of books out there about cops and street cops and what they’ve done on the street. He said, so he said, oh, but he started to now expand on it. And then he told me the second part of his career, which was the prison ministry in the federal prison and a state prison here in New York. And I said, Jimmy, you buried the lead. That’s the part of this book that I can sell to a publisher. Because Gary, you probably know this. You probably interviewed these guys who do books when they retire. This was just going to be one of those. Jimmy’s career on the street was terrific.

    [6:47] The only problem was there are lots of guys who have books out there like that. So when he told me the story about his prison ministry, I was working at the time with a partner of mine, Jerry Schmetterer, who has now passed away. And we both talked about it and we said, this is definitely a story. This is definitely a book. And it’s been a long journey, Jim, until we got to this point. We’ve had COVID. We’ve had the Minneapolis, the guy in Minneapolis who was killed and agents saying to us, nobody wants to publish a book about a good cop. Nobody wants to do that. You can’t sell this until I didn’t give up. I really didn’t give up. And I took the proposal and I rewrote it after Jerry died. And then I sent it out to a couple of publishers and one of them grabbed it and said, yes, I want to do this. And then believe it or not, Gary, his publishing company hit the skids in terms of being able to spend money. He went out of business. So I had one more shot and I gave it to the publisher of my novels.

    [7:55] And she finally is the one who said, yes, let’s do this. And then here we are today.

    [8:01] It’s really, again, I said this before, but it was a journey of love. It really was to tell this guy’s story. and we, I know I’m repeating myself, but we became such good friends that our families got to know each other. I went to Jimmy’s house for holidays. We really just became very good friends. And here we are. And I’m so happy that I was able to write this book because I really believe that the people who read it will say, wow, this is a great guy. This is a great guy. And he is. Interesting. Hey, Jimmy, I got a couple of questions for you. Now, you worked, that was the Rocco and Lori case, if I remember right. And everybody who worked big city policing at the time, that scared the dog shit out of us. It was like these guys just laid in wait for a couple patrolmen to walk by, stepped out and shot them. That was my impression. And I worked that kind of a neighborhood. And we were jumping. We were pretty jumpy for quite a while. And it wasn’t solved for a while. We knew it was some kind of a political act, or at least that’s what we’re led to believe. Did you guys feel the same way in New York? Let me just stop you for a second. The case that I did with Jimmy was Norman Cerullo and Christina Soames years later. The one that you’re talking about, Rocco Laurie and Gregory Foster, was much earlier.

    [9:21] Jimmy was involved in it because he was a good friend of Rocco Laurie. They went to the academy together. But I’m sorry to interrupt, but I just wanted to make sure that we were talking about the right thing.

    [9:33] So that kind of a case, you actually went through two of them. So tell us about your feelings about that. Did that, how did that affect your dealings on the street? I was in the academy with Rocco Laurie, right? And we had both come out of the Marine Corps at the same time. And we worked out together. We boxed together. And some of the guys were slacking off. The guy’s name was Mr. Clean. He was the instructor. He would say, okay, now you’re going to box with Denny or you’re going to box with Laurie. Of course, they were slacking. We weren’t slacking. Oh, God. That was me. They said, Jenkins, go over there and box with one of those guys. No brother in Lime.

    [10:12] So we became close we we knew his wife he knew that time it was my girlfriend but that was my wife we had gone out to dinner and he was a really good man in the academy i won the gun for physical fitness he won the gun for overall excellence and we got pictures with our guns together and stuff. So I was working at midnight with this guy, Victor Grillo, nice guy. And a job came over. Cops shot in Manhattan. We were in Brooklyn. It’s on the other side of the bridge. So we’re saying, wait. And that became the ninth precinct. That’s where Rocco worked. So we used to call him the Rock. I hope it’s not the Rock. And it turns out it was him. These guys executed him. They were basically a domestic terrorist group. They were robbing banks. They were killing cops for no reason. They just walked past them, turned around, opened up on them. And they shot them all over the face to the groin. And then they took their guns and shot them. And some of the guns actually wound up out in St. Louis or in West Area.

    [11:16] So did it affect me? Absolutely. I became, I don’t want to say callous, but I was very leery of everybody.

    [11:26] And I started, my niche was guns. I locked up a lot of guys for a lot of guns. But anything to do with it, Black Liberation Army or anything, I used to accumulate information, intelligence information, and my locker was full of it. I’d lock up a guy, and they used to have years ago the little address books. I used to take their address books, and they would ask me information, the FBI, the Major K-Squad, Jimmy, have any information on this guy? And which I did many times, right? Fast forward several years later, I’m out, and I’m having a few cocktails, and then i drove back to the precinct the 79th precinct to meet a friend of mine bobby perry, and while i was at the front of the desk there’s a place they could check your messages if anybody calls you messages so i’m checking my messages and it came over shots fired then it came over cop shot then it came over two cop shot then i drove down to my civilian car right it was dark, and it was like help you know radio card door is open you know I mean blood all over the place he also shot his friend right and he’s laying it dead with a gun in his hand his blood all over the place it was a nightmare so let me figure this out but now everybody name others coming down because he’s cop-killing students a doubleheader so to speak and then I see the blood going across the street and the blood stops.

    [12:53] So obviously somebody was shot. It’s not our guys. And then I assume he got into a car.

    [13:00] So I’m trying to figure, is he going to go to the Spanish neighborhood or deeper into the black neighborhood? And I said, let me go to the hospital. So I drive to the hospital to see if they need blood or anything. And out of the corner of my eye, when I passed Lexington Avenue, I see there had been a car accident. A guy hit parked cars. I kept going. And then I told Mike, you know, my father gave us a game when we were kids. It was called Game in the States. at a map of the united states and you had two little electric wires and you plug one into the state and there’s a list of capitals on the other side and when you hit that the light would go on you got the right answer and as god is the lord a light went off in my head just like it was the right state capital yeah went to the hospital and they did you know and then this guy paulie has ever seen him he’s crying he was in plain clothes anti-crime i said paulie listen to me Two things. Once, I want to come in the car. I’m going to go back to the scene. Because when I got there, there was a Spanish guy on the pool across the street. And he was a little biggazy type guy himself. But he used to give me information. He used to give me information on his competitors. Yeah.

    [14:10] Yes. So when he saw me, you know, he ran. Right? I wanted to come back and talk to him. But on the way back, I said, Paul, I’m going to stop at this accident scene. This is, it’s just there. Yeah. Go back there. Ambulance is starting to pull away fire truck was there pulling away so i went over there they said it’s an accident scene the guy’s injured i said what kind of injury is it the guy said well he dressed his wound because he won he refused medical aid this guy so i said i just dressed his wound i saw undress the wound let me look at it i’m not undressing the wound i went over and i just ripped it off and it’s a gunshot wound yeah right yeah so all he had a radio calls the sergeant down and they bring a witness from willoughby avenue she comes down she says that’s the guy who killed the two cops so we get him put him in the ambulance right in the ambulance he’s a big boy this guy right and he goes reach and grabs my gun from my holster so now it’s like an arm wrestle for the gun between me him and paulie saracena and during this arm wrestle necessary force was used and the necessary force was used until he dropped the gun or he got the gun from him. Goes to the hospital. He has a Derringer behind his belt buckle and he has police handcuff key.

    [15:38] These guys are the real deal. Yeah, that’s a real deal. They train for this stuff. They associate but others that train they shoot you know what i mean so it’s just uncanny that rocko was my friend and he was murdered in a double police homicide and then a few years later i lock up a guy from the same team that killed two of my friends you know it was a nightmare and then we went to trial and that’s how i met mike and it’s a very.

    [16:09] It’s pressing on your brain. Yeah. Something like this happens. And then, and I don’t have to tell you, Gary, but then you get other cases. So you’re making more gun arrests, but you still have this. You know what I mean? It’s, it’s tough. It’s tough. But it was. I just want to interrupt for one second. One of the, Jimmy mentioned her. They brought a witness back to the scene to identify the, the bad guy. And, uh, and she was a great witness. She was there when the shooting occurred. She was actually moving into the building that the shooting happened in front of. And so the case was, we had a couple of, she was the best eyewitness to the case. And as Jimmy and Tony Martin, the detective who were assigned together after the actual arrest, because we had, they had to get the case together and look for more witnesses, et cetera.

    [16:58] They went one day to see this particular young woman to talk to her and see what was, if everything was still good, if she was okay. Turns out she was in the hospital nobody knew this she had gone into the hospital we were told because she had a cold she died in the hospital gary from a cold which is what we thought turns out she had encephalitis but the thing was at the time we said who goes into a hospital number one with a cold and who dies from a cold so we at that point not me but i wasn’t on the case yet, but others. And then when Jimmy told me this later on, I said to myself.

    [17:42] It’s got to be some connection to the bad guys. Maybe they poisoned her. Maybe they did something and we looked into it. It turned out, Jimmy, what was the disease that she had? I think she had herpes viral encephalitis in the brain. It’s a possibility that it can be induced. Yeah. So that’s what we looked at. And the medical examiner at the time of the death never really looked. The DA who had the case at the time thought, ah, this is a slam dunk. We had this witness, that witness. Jimmy arrests the guy and he’s got the bullet, which another thing happened. He wouldn’t allow the medical people to take the bullet out of his leg. It was the cop’s bullet. Yeah. So we wouldn’t, he wouldn’t let him do it. So we had to go with a, an x-ray of the bullet at the trial instead of the bullet itself. But it was, it’s a case with, as I said before, excuse me, many twists and turns. And it’s the whole story is in the book. And I don’t want to take away from Jimmy’s story here, but I have a legal question. You couldn’t get a search warrant to take the bullet out of a person. Is that?

    [18:51] We tried, and you know what the judge said? No. Uh-huh, okay. I just, I never ran into that. I’ve heard that before where the bullet stays inside and you can’t get it. I just.

    [19:03] I tried. The judge wouldn’t give us the search, the ability to search, quote unquote, which meant taking the bullet out of his leg. Anyway, so that’s where we, that’s where we met. And it was, it was quite a case. And Jimmy, I understand you, you go through your career and you see all these horrible things and you’re harding yourself. And you know, the title of your book, hard girls, hard boys, hard men cry. I don’t know why I got hard guys cry. I don’t know why I can’t remember. I should remember from Norman Mailer’s tough guys don’t dance, but hard guys cry. And so you harden yourself all those years, but then something happened in your life. Apparently that changed, changed that. I know after I retired, partly what happened to me is I became a lawyer and I started dealing with people from not particularly criminals, but many times relatives of people who had gone to jail. And I worked for public defenders and really got to know people on the other side and realize that we’re just two sides of the same coin many times trying to get along and trying to get by. So what happened in your life that changed that, your attitude?

    [20:11] When I retired, there was an old man who was a farmer, and it was like a late-year-type situation. This farmhouse was falling apart. The second floor was owned by raccoons. He had electricity in one room and no running water, but he was the calmest, nicest, most spiritual guy you ever wanted to meet. Almost no teeth. He had one tooth. And there was Louis Adamski. We used to call him Louis the farmer. So I used to take care of Louis. was taking over my house for Thanksgiving, Christmas, driving down this long driveway, see how he’s doing. And I didn’t see him for a while. So I drove down the driveway one particular day and I said, Louie, I haven’t seen you. You haven’t called. He said, he had bladder cancer. I said, really? I said, wow. He said, you had two surgeries. I said, you’re going for follow-up treatment? And he said, I’m supposed to go every 90 days, but he had no insurance, zero, no Social services, nothing. And the doctors were suing him. And they wanted his farm. He owned one-tenth of his farm. It had about 80 acres. But it was heirs. Everybody in his family had passed away. I said, Louie, you got to get follow-up treatment. So there was a city that’s not about a half hour away called Newburgh, New York. And there was a urologist I was familiar with. So I told him the story. This guy has nothing. He said to me, if you will drive him, I will treat him like the president of the United States.

    [21:40] So for two and a half years, just about every month, sometimes twice a week, it all depends when his visits were, I would drive Louie. So it was like an all day affair almost because I have my own business, so I don’t show up for work. What do I care? So I take care of Louie all this time and my friends are patting me on the back saying, oh, you’re Louie’s angel. So one particular day we go in and…

    [22:03] He, if Louis checker, he calls me into the, uh, his consultation room and he says, so your friend’s cancer is back. She got to be kidding me. He said, yeah, I feel it on his prostate. He said, he has someone for biopsy Friday. This was on a Wednesday. I said, I don’t know how he’s going to get there. It’s an old day. I said, doc, listen, I’m married to this guy for two and a half years. I said, I’ll take him. He said, you sure? It was an old day. I said, doc, I don’t care. He said, all right. He said, I’ll tell you what, as long as you’re going to take them, your PSA is just borderline high. He said, I feel there’s nothing on your prostate, but if you’re going to take it, let me give you a biopsy too. I said, fine, I don’t care. So I take, we both get the biopsy. The next Wednesday, he calls them both of us in. I have cancer as well, worse than his, right? So he got radiation. I went out to New York City. There was a top flight surgeon in Columbia Presbyterian Hospital. And I told him the story like I’m telling you now. So he said, you got to cut that out of there. You don’t want it in there. So they cut me a half. They took it out. And in the recovery room, he comes in and he says to me, you weren’t Louis’ angel. Louis was your angel. He said, you had a C-grade cancer. It was starting to spread, but I got everything.

    [23:15] So he said, you would have been dead about a year and a half. He said, because you had no signs, no symptoms. By the time you had the symptoms, it would be all over. Yeah. So it changes the way you think that I was invited to go on to this, a religious retreat weekend, a Cresillo weekend. I didn’t want to go. I’m not a holy roller. It’s not my cup of tea, but I socially boxed in like friends. So then your wife has to go too. So my wife, Noraline said, oh, I’ll go. And I said, oh, yeah, now I got to go. So I go on this week. it’s it’s thursday friday saturday sunday you can’t bring a watch you didn’t have cell phones then right so you’re stuck there so i went and i hooked up for a couple of other ex-marines and this actor mike was poorly he was on the sopranos so i sit in the back like we’re just going to ride this one out oh we can write it out it turns out that it was very moving, it’s very moving and people spoke that thought they were like punks i knew them indirectly they had quite a story to tell and then, weekend was over and on the way back it was November and I was telling Mike I rolled the windows down it was like spring, spring in my mind you see things differently like these computer generated pictures you see what it is but if you stare at it long enough another picture comes out within the picture and kind of life came out of life for me I saw things differently, Then these guys asked me to go into the prison.

    [24:42] Listen, I say, listen, you’re a carpenter. You’re a plumber. You don’t know what these guys are. I’ve thrown these guys down stamps and shot a guy at my house. Crazy. Again, I’m socially boxed in. So we go up to the prison. It was 41 of us, 41 of us. It’s called the Kairos. It’s an interdenominational…

    [25:01] Prison ministry. So I sit in a big circle, piece of paper, it passes around. When you get it, you have to say who you are, where you’re from. So I get it. I said, my name’s Jimmy Danity. I live in Orange County, New York. I’m married. I have two children, and I retired from the Oak City Police Department. They booed me. I told Mike, it was like an old dog growling. Yeah. Yeah. I said, what am I doing here? So the next day, because you had to sleep up in the prison too, The next day, you’re at a table. So you have an inmate on either side. So there’s like maybe nine people at the table. And there’s three of us, six of them. And don’t ask them what they did. Never referred them as a prisoner, as a resident. They were like, guys, I grew up with their neighbor. I said, what did you do? You stupid. So it becomes, it was a religious weekend. But also, it’s practical life. And you guys were good. You know what I mean? I got along well with them. So we did every day and it was friday saturday sunday they finished and that’s it i’m done i’m done with this i said i’d do it and i’m saying i wonder if any of my guys would show up to a wednesday night they have a wednesday night follow-up at this organization i wonder if any of my guys would be there so you know what let me show let me go to one wednesday right all my guys.

    [26:22] Oh, my gosh. And that was the only, Gary, that was the only table where all of them showed up again. So that’s why he knew that this was the right thing for him. I’m sorry, Jim. I just want to know. And so this was still in the prison. Yeah. Back up the prison. Yeah. And they invited these guys. If you want, you can come to this follow up. At that time, every Wednesday at six o’clock, they could go into the chapel to this particular group meeting. So I just want to see if any of my guys are going to show up. They all showed up and then the volunteers drop off and then i said let me do another wednesday, and another wednesday and it comes like everybody wants to talk to you it’s like when you go into the pet store where puppies say they want you to pick them like pick me and it you get you wind up with a group i tell mike they’re my guys and then you wind up it’s a spiritual thing no question about it right it’s brand involved and everything but you go through life with these guys and a lot them have a lot of crazy situations yeah and one guy is a mafia guy and i think frankie and he wants to say jimmy this new guy he wants to talk to your jug it’s all right so he takes me behind this little interdenomination altar they got there right so i said hey don’t you he says remember me i said no he said you should you broke my nose so i said when did i break your nose He said.

    [27:46] Yeah, in the park on 53rd Street where we used to play hockey. He said, your brother, I remember you. I mentioned his name, his last name. I said, you were messing with the park attendant. I slammed a basketball in his face. You know what I mean? He never forgot it. They told Frankie, yeah, he was crazy before he went to the Marine Corps. I’d make guys in there.

    [28:04] I worked. Yeah. The drug cases that they had.

    [28:09] You know, I knew who their bosses were. I testified in Philadelphia against one of these guys’ big bosses. And it’s just, it was like almost an inside straight. It was like meant to be. It was meant to be. And then my parish priest, so then I started, I was in the denominational night. The Catholic guys had nothing. I started a Catholic night with a few other good guys, my friend Brian and a few other guys, right, on Thursday. So now I’m going there Wednesday and Thursday. So my parish priest said, the state maximum security doesn’t have anything like this. Let’s start one there. So I’m going Wednesday, the federal prison, Thursday to the state max. You know, and it, I did it for 25 years, two days a week. Wow. And if the guys in Brooklyn, where I was a cop, knew I was doing this, they say, wrong guy, definitely. Somebody else, you got the wrong guy. Yeah. It’s the way the good Lord leads you. Now, something changed in your life and it’s not like you had any control of it. It just, it changed. You opened yourself up. It seems to me like it. And you just didn’t have any choice but to go down this path. And you know what it is also, Gary, it’s also like you’re preventing crime. You’re doing the same thing only from the inside. From the inside, you want to change the way they think, the way they act. And there’s a million things I could tell you how I was able to change things in a prison. They’re going to stab somebody. The guy who was a rat.

    [29:32] And they didn’t like him. I didn’t like him. And I told him, listen, I like the guy. He said, you like the guy? Don’t get involved in this. I said, do what you want to do. I like the guy. They never touch the guy. Because if they do something like that, then they’re going to hurt you.

    [29:46] Gary, I think Jimmy should tell you, he’s talking about the effect he had on these guys. What really was the point of the prison ministry was to essentially make these guys, I think, better people and to change their lives. I think you should tell him, ask Jimmy, tell him the story of the Boston mobster because this one, this story has, it really hits home as to exactly what effect he had on someone who was one of guys that you might have on your show. someday. This guy was a really bad guy. And he was up there with Whitey Bulger, et cetera, in Boston. So I think it’s worthwhile to tell the story. And it really hits home in terms of how effective Jimmy was after being effective on the street, locking up these guys, what he did with the prison. So if you have a bit of time, I think it’s worthwhile to hear the story. Yeah, let’s hear it. I always want to hear stories about mobsters, anyhow. Yep. Go ahead, Jim. We were up at the federal prison, and it was during the holiday season, right? And the volunteer chaplain was Father Paul Papara, and he was giving a talk on forgiveness. So we had all these wise guys. It was a mess. They had all different guys. This particular time, a couple of wise guys, they had their arms folded, and they said, Father, you want me to forgive the guy that ratted me out?

    [31:05] He’s home with his family, and I’m here doing X amount of years left on my bid. So I raised my hand. so I said listen if this guy is lying and put you in prison for no reason shame on him he should rot in hell but if he just exposed what you did anyway you know you did it if you did it the good lord see you live in a fishbowl the guy just exposed you for what you did that’s, You have no bitch here, pal. Jimmy, this guy Jimmy, he’s a different name than him. Jimmy stands up and he says, listen, I’ve been in jail. I’ve killed people. I don’t want to, I forgive anybody. I want forgiveness. I’ll forgive anybody. So that was it. Eventually, Jimmy, a couple years later, goes home. So he called me at my office a couple years later and he wanted me to write a letter of reference to work at the docks with Homeland Security. I said, I don’t know how to write it. Put down that I was a prisoner and just what you thought of me. No problem. So I met him in the prison, stuff like that, right?

    [32:03] About a year after that or so, I get a call from him again. He says, hey, Jimmy, you got time? Hey, Jimmy. I said, good. I got all the time in the world for you. He said, what’s up, pal? He said, I was on a train platform. He says, and I see this guy. Him and his associate tried to kill me. They had stabbed me 13 times. He said, I already took care of his friend. And I walked up to him like a face-to-face with him. Then he recognized me the guy turned white and urinated all over himself because he knows he’s there jimmy says to me i put my finger on his face and i told him you know that thing you’re worried about right get out of here i forgive you i get the fuck out of here now and he says to me jimmy it would have been easier for me to clip this guy and to forgive the guy but i forgave him, And I’m saying, Jimmy, I’m so proud of you, I can’t, just, and he, for him to call me to tell me how he responded to that situation, you know, which was completely out of character to the old guy, the old Jim. He was very proud of himself, and I was very proud of him.

    [33:09] So that’s the story Mike has told. It was the story, quite frankly, Gary. Didn’t he have one of the Westies in there with him? They were some particularly brutal crew in New York City. Yeah, yeah, he did.

    [33:25] We had a few of them up there. We had Jimmy Coonan, who started the Westies. Oh, okay. Jimmy was there, and I was friendly with Jimmy because I knew guys that he knew. The guys at Otisville Prison is a high medium.

    [33:38] Lewisburg is a max so when guys behave even a max they could come down to the media so when he came down he never came to the services and stuff we were talking all the way on the side but another fellow was a Westie a tough guy you know what I mean they would, drive through jewelry stores, 50 miles an hour go inside and rob everything but they would go in there before with their girlfriends looking good dressed nice they knew where this stuff was and they would take everything and he wound up getting locked up for almost like a Lufthansa type thing at the airport only they got caught so he was at my first weekend in the prison and we became very close friends and I tried to help him and he responded very positively, and he’s sitting in a circle there’s a cross, whoever has the cross has the microphone, nobody interrupts when you’re done, the next guy talks, he was talking and we finished, the Spanish kid so the Spanish kid is talking and he’s talking, so I told him what are you talking for Rich he can’t be talking like that the kid’s talking so he didn’t come for a few months then he comes back right and we’re sitting there talking and then he has a cross and he puts his head down.

    [34:54] And he starts talking and he says, you know, something happened to me. You can’t explain it. You had a Spanish kid in the next cell, right? It was a new guy. They robbed the sneakers and the kid had no sneakers. I know he’s got his head down. Now I’m thinking maybe he robbed the kid’s sneakers, right? He says, I gave him my sneakers because I had an extra pair. And as he’s telling the story, his head is down. The floor is gray, but getting darker, the teardrops. He’s telling the story he’s crying and then he says maybe I’m not all bad after all yeah I said how can you think of yourself like that he eventually goes home so, we my wife Norley and I get invited to his wedding which is a no-no but the guy was home so and the wedding is on Mulberry Street in Little Italy.

    [35:46] Yeah so we go down at the wedding and we’re like the oddball there but He could introduce us to enough people, you know, and if you see change in people, it’s wonderful. If on the street, if you go to these religious retreats, people go jumping out like a gazelle. But in prison, if an elephant jumps in it, it’s a miracle. Yeah. I mean, if you see somebody that thinks that they’re ugly, they’re not ugly inside. So I found it very rewarding. And. They, I didn’t think they’d respond to retired law enforcement, but they responded well. Yeah. Because I spoke their language. Yeah. So it lasted 25 years, Gary. Yeah. I’ve got a couple of guys here in Kansas city that it’s not a spiritual kind of a thing, but I’ve become friends with them. And one guy told me, he’s fine. He said, he said, I can talk to you and you understand what I’m talking about. He said, all the rest of the people in my life anymore, cause he’s out of the life. He said, they don’t understand what I’m talking about. He said, I don’t have to get back into life, but I can talk to you and you know, you know, the people I’m talking about, you know what I’m talking about. I said, yeah, I do.

    [36:56] So obviously in case it was pretty obvious that we were, when we started to hear all these stories, when he told, told Jerry and I the story of the, the mobster who was crying because given the sneaker, that’s where the books, the title of the book comes from, art guys cry. But there’s one other guy in there that you should ask him about. And that is we had this, I don’t even know what to call him. He was really an oddball guy, a criminal in New York. He was a rich guy who owned a lot of, he ran art galleries and collected art galleries and collected paintings and got into the art world and was advising rich people as to what art they were buying. And it turns out he was basically a sadist. And he had another guy with him who he and the other guy wound up, he didn’t get charged with this, his partner did, wound up killing somebody. And when they found the body buried laying in the woods in upstate New York, he had one of those.

    [38:02] Sadomasochistic masks on him, his black mask. And this individual was one of Jimmy’s guys and he was a hardcore, am I right, Jimmy, in terms of not wanting help at all. He was just the kind of guy who, you know, if you help them, it was going to be a miracle. And he did. He helped them and it’s a miracle. And it’s worthwhile to tell the story about this guy. His name was Andrew Crispo. He’s no longer alive. And he was all over the newspapers here in New York City because of the whole masochistic, the sadomasochist activity that he was involved in. And that the picture of the dead body with that black mask on was all over the newspapers. And this guy, we have his picture in the book. If you see him, it’s butter wouldn’t melt in his mouth. He looked like the nicest guy in the world. Businessman. Turns out he was really one of the worst guys in terms of how he treated people. And Jimmy finally got to him. It was, to me, one of the more miraculous transformations when I heard all of the stories was this one because of what he was on the outside and what he became after Jimmy had him and he got out. He did not repeat his life the way that he was before here. Chris Bowe was a tough guy, right, Jimmy, in terms of getting to him?

    [39:28] Andrew, Sky Andre brought him down to one of our groups. And he asked me if he could bring his friend down the shirt. Everybody’s welcome, of course. And you’ve been around tough guys your whole life. Everybody’s a tough guy. You’re a tough guy. Everybody’s a tough guy. This guy had no muscle tone. He was like ashing in color. He looked like a raccoon. He had like rings around his eyes. And he was like creepy, creepy. So he came. And then he came for about seven years all the time. You get to know him, right? And he got grabbed for that sero-masochistic murder, but they couldn’t prove it. He got locked up, attempted kidnapping, the three-year-old daughter of the federal trustee. That’s why he was in jail now federal jail but he if you make a long story short he, doesn’t know who his parents are right and i’m not bleeding on i’m just telling you the way it is, he was dropped off at an orphanage as an infant and i was there for sentencing and this is what the judge said mr crispo he said before i sentence you i’d like you to know that i researched your history as a newborn you were dropped off in an orphanage right you remain there for 18 years where you were repeatedly beaten up and raped and.

    [40:47] But after leaving there, you managed to raise yourself up to get on the top of the art world, even owning a world-renowned art gallery in New York City. He said, for that, he said, I give you credit. However, then he banged him for seven years on the other thing. But he came down, and he had nothing spiritually. And if you sit with him and you talk with him, he kind of listened. He came around.

    [41:13] Like I told Mike, there was another guy. colombian guy his wife used to bring his daughter to work all the time so he came into the group a little late and he’s crying and then i said what’s the matter he said he said i’m not gonna see my daughter for two weeks i said well the comment told me once there’s a price for loving the price for loving is the absence of love you have to experience the love to miss it mr andrew who was sitting on our group andrew could you tell him a little bit about yourself oh yeah he said see the visiting room that you were in with your wife and the child, I’ve never been in there, and I’ll never be in there. And they said, there’s nothing worse than being alone, than being alone and no one cares.

    [41:56] And he came, and the rings went from his eyes, and then he became involved in all this other stuff. And he actually became a kind guy. He got involved with the church and things like that. And then he eventually went home. I’ll tell you the money he had. You need the money for an appeal? He sold one painting for $2.46 million. Oh wow the attorney’s fee that’s just one thing he had money but he had nothing yeah he had nothing and then when he went home he used to correspond you know and he’d write beautiful things thanks for the prayers thanks for your wife how’s your dog it’s not the same guy but he wasn’t like like what he’s tattooed tough guys he was like creepy tough and at the end when he left my opinion He was not. So if you can help somebody, it’s nice to help somebody if you can. Yeah. That’s interesting. That’s a true shift in the personality and to give somebody some spiritual hope in their life that they can, from what you’re describing to what he was to what he left when he left. That’s amazing. Exactly. That’s an amazing story.

    [43:01] There it is. Cry, The Journey of a Tough Cop from the Mean Streets to a Prison Ministry, Jimmy Dennedy and Michael Vecchione. Jimmy and Michael, I appreciate you guys so much for coming on and telling these stories. And guys, there’s a lot more stories just like this and better in the book. I’ll have links to get it down in the show notes.

    [43:22] And guys, you got anything last words you want to say? Anything you left out?

    [43:28] Gary, listen, keep getting those pension checks.

    [43:33] Yes, I will. I told my wife, Nora, put my feet in potting soil. If my toenail grows, that’s a sign of life. Keep getting that check. Really?

    [43:44] Thanks so much, Jimmy. All right. I just want to thank you. You’ve been terrific. And I hope that, I really mean this when I say this, people who get this book and read it or listen to it or however they want to get it into their, their mind, they’re going to love it because this guy’s story is just fantastic. And we touched on a few things, but we didn’t really touch, we didn’t get into the real meat that that’s there. And it’s, it was a, again, a pleasure to do this. So I’ve got one guy, I got one guy I talked to that has prison stories. I tell you what guys, there are so many great stories that come out of the penitentiary. It’s just, it’s amazing. I think part of these people don’t have much else current to talk about, so they tell stories from their past, and you get some great stories coming out of the prisons. Thanks a lot, guys. Gary. Thank you. God bless my friend.
  • Gangland Wire

    Louis “Streaky” Gatto: New Jersey and the Genovese Mob

    22.05.2026
    Retired Kansas City Police Intelligence Unit detective Gary Jenkins examines the rise and influence of Louis “Streaky” Gatto and the Genovese crime family’s powerful New Jersey faction. Drawing from a 2004 New Jersey Crime Commission report, this episode explores how Genovese crews operated across multiple counties while controlling illegal gambling, loan sharking, and waterfront rackets through intimidation and organized violence.

    Gary breaks down the structure of Gatto’s Bergen County crew, including the involvement of his son Joseph Gatto and son-in-law Alan “Little Al” Greco. The discussion details how the crew maintained control over bookmaking and gambling operations and how prosecutors later tied key members to murders connected to their criminal enterprises.

    The episode also dives into the federal RICO prosecution and the dramatic courtroom testimony of witness Robert Belli. Gary explains allegations that associates of the Gatto crew attempted to pressure and intimidate witnesses before testimony, including claims involving the infamous “evil eye” or malocchio. Prosecutors argued that subtle intimidation tactics, courtroom stares, and indirect threats were all part of an effort to influence testimony.

    Another major focus is Moe Brown, a reputed associate connected to the Gatto organization. The episode explores how prosecutors used recordings and testimony to connect Brown to the defendants and how his conduct in court became part of the government’s intimidation narrative.

    Finally, Gary examines the later criminal cases involving Joseph Gatto, including offshore sports betting operations, convictions, prison sentences, and the eventual decline of the family’s gambling empire. The episode concludes with the deaths of both Joseph Gatto and Louis “Streaky” Gatto, marking the end of an era for one of New Jersey’s most feared Genovese crews.

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    Transcript

    [0:00] Hey, all you wiretappers, good to be back here in the studio of Gangland Wires. A little extra I’m going to throw in here. I did this interview with Scott Deitch about Jerry Katina, and I got a lot of.

    [0:12] Comments, a lot of reactions to that show, a lot of New Jersey mob fans, Genovese mob fans out there. A guy named Carmine, Carmine something, he had some other numbers after his name. Carmine commented that I should do a show on Louis Streaky Gatto. That was a New Jersey capo who was one of the Chin’s best earners in the Genovese family. He had a crew down in New Jersey. And if you notice, one more thing, I was going to mention this before. I got a new hat. Now, check this out.

    [0:46] Hope you can see that. Got the gangland wire insignia on it. Now, this is my official gangland wire hat.

    [0:56] Louis Streaky Gatto, the New Jersey Crime Commission report in May 2004, reported that the Genovese family maintained five crews headquartered in New Jersey. Each was overseen by a capo, of course, and each of the four New York-based crews, this is right out of The Sopranos, about 40 soldiers and more than 400 criminal associates who were active in New Jersey.

    [1:21] They reported that the family operated in the northern New Jersey counties of Hudson, Essex, Union, Bergen, and Passaic County. They also had gained strength in Middlesex, Monmouth, and Ocean counties. Ocean, is that down in Atlantic City? I don’t have a map in front of me, so I’m not sure. The crime report stated that the Genovese family controlled the largest bookmaking and loan sharking rings in the New York, New Jersey metropolitan area. And the family maintained a strong influence on the Port Newark, Elizabeth, and Hudson County waterfronts. This report also identified the family consigliere Lawrence Little Larry Dentico as a person with the most extensive familiarity of the family’s New Jersey operations because he had been the top aide to the former consigliere and New York, New Jersey operations chief, Louis A. Bobby Mann. I did a show on Bobby Mann and Irwin Schiff and some of those plots, I don’t know, sometime in the last year, I believe. This 2004 report identified the five capos at that time in New Jersey, and they were Tino Fouimara, who died in 2010, Angelo Prisco, who died in 2017, Joseph Gatto died in 2010, Silvio DeVita, and Ludwig Bruchy, who died in 2020.

    [2:44] Now, Streaky Gatto, Louis Streaky Gatto, he was always the favorite money earner of Vincent de Chin Gigante. Before he was promoted to captain, his New Jersey crew was led by a capo named Peter LaPlaca until the mid-1970s, and that’s when Streaky Gatto took over the crew. Gatto was the boss of Bergen County with the help of his son, Joseph the Eagle Gatto. And his son-in-law, and a guy who keeps coming back in this thing, and who was his top enforcer, Alan Little Al Greco. I noticed a comment. Somebody said that he was really half Polish. I think his mother was Polish and his father was Italian. Somebody correct me on that in the comments, if you will. Controlled large illegal gambling, loan sharking, bookmaking operations in Bergen and Passaic counties.

    [3:33] These three guys used murder, violence, and fear to click on these rackets and control everybody who was a bookmaker. You couldn’t be, like Chicago, you couldn’t be a lone wolf bookmaker making money without these guys getting a piece of your action and working with you on it. They made sure that other rivals didn’t take advantage of somebody that was

    [3:55] under their protection. Gatto and Alan Greco, Little Al, were indicted on two counts of murder for the murders of Arthur Belli and Vincent Mastretti. They also were alleged to be behind the murders of a guy named Jack Handsome Jack, Ciaranella, Johnny Lombardi, and Peter Adamo. 1991-1990.

    [4:20] Streaky Gatto and Alan Greco were sentenced to 65 years. Streaky Gatto’s son, Joseph Gatto, was indicted on racketeering charges in the same RICO prosecution, but he only received 30 months. There was an appeal to that trial, and we learned a little bit about their brazen intimidation tactics, how it works. There’s a guy named Robert Belli, whose brother had had a gambling operation. His brother, Arthur Belli, was one of the persons in that RICO case that was murdered by Streaky Gatto. They called on Robert Belli to testify about the extortionate takeover of their gambling business. And he said that little Al Greco once told him, he said, things are going to be different now. And then shortly after that, Robert Belli’s hot dog truck was blown up and he was beaten by two men with baseball bats, typical mob extortionist takeovers of a small-time gambler, a bookie, a guy that had his own book of business, his own customers. As a result, he just gave it up. But he also testified that Belli disappeared and now we’re in trial for Belli being murdered by Streaky Gatto and planned on returning to the business just before he disappeared.

    [5:37] Now, in cross-examination, it turns out that he had been spoken to by somebody in the Gatto families because he all of a sudden starts agreeing with all the defense counsel’s suggestions, first of all, that the prosecutor paid him and pressured him, and all the local police and prosecutors involved in the case were corrupt. I’ll redirect. The prosecutor tries to show that Belli had become hostile to government and accommodating to the defense because he’d been intimidated. They asked Belli about a guy named Frank Sesta, who was known as Mo Brown. We’ll refer to him as Mo Brown. He was always known as Mo Brown. Belli stated that after defense investigators, Gatto’s lawyers and their investigators handed him into a meeting with the defense counsel, Mo Brown showed up and wanted to take him to the meeting. And then when he wouldn’t go with Mo Brown, Brown tried to pressure him into letting one of his associates drive him to this meeting and again to a pretrial hearing. He wouldn’t do it. He knew better than that. He took a ride with a government investigator. He did have to go meet with the defense counsel, of course. Anybody that’s going to be a witness against you, they have to make them available to the defense investigators and counsels, defense counsel, in order to do a deposition or just listen to what, see what they got to say.

    [6:59] He said Brown approached him and told him about a job interview. He said he’d take him to his job interview just before he testified at trial. He said Brown had discussed the case with him more than once and once said, isn’t it a shame that Little Al got 60 years in this case and he did get 65 years? And this all was coming out after they got their 65-year sentences, Little Al and Streaky Gatto. They just kept coming back. And then during the trial, the prosecutors got testimony from Belli that Moe Brown had been in the courtroom and standing directly in front of him several times and that he looked at him with an unhappy look.

    [7:36] Of course, they objected, the defense counsel objected to all that. They also introduced evidence that this Moe Brown was really closely connected to Streaky Gatto and Little Al Greco. They’d sent him into surveillance during the social club, the Lodi Social Club, and sent him with other people in the defendant’s gambling business. They also had a tape of a conversation between Louis Gatto Jr., Stryker Gatto’s son, and little Al Greco, talking about Mo Brown, that they were real familiar with him. So they connected Mo Brown to the Gattos and to Little Al Greco and then showed how he was then in court and was given the witness, the evil eye, the malokia, I think they call it, something like that was in The Godfather. And that he had tried to befriend the guy before he testified and told him about a job and tried to give him rides different places. They even mentioned that how…

    [8:39] They asked the witness Belli about three occasions during the trial when Al Greco had given him a look. One was before he testified, and Greco passed by him in the hallway, and he gave him a look. Defense has strenuously objected to this. It’s irrelevant, and you can’t really say that look was a bad look. The defense counsel strenuously objected to these points, but it was overruled. The second look came when Belli was in the back of the courtroom him waiting to testify, and Greco, Little Al Greco, just turned his chair around just to give him a look, and the third time was when Greco stood up and then turned over around and looked at Belli during the sidebar while Belli was on the stand. Prosecutor then asked Belli if Greco had ever looked at him that way before, and Belli said, well, he had. He said when he told him, Little Al Greco told him things are going to be different just before he beat him up, or had he beaten, And, of course, they strenuously object to all this. In the end, it did not do any good. In the end, little Al Greco still got his 65 years, and he didn’t get a new trial or anything.

    [9:45] A little story in regards to little Al Greco, the guy that was son-in-law to Strique Gatto and was right under him. It seemed like he was his main kind of enforcement guy, guy out dealing, maybe underboss, under people trying to, guy that deals with people on the street. He made a connection with a notorious New Jersey con artist and mob associates, Tom Giacomaro. They wanted him to come in and be a made man, supposedly, in the 80s. And, you know, he didn’t want it. He was independent. He knew better because once you come in, you know, they’re going to take everything from you. And he was quoted as saying, you know, I don’t want to kiss the ring. Everybody’s kissing Streaky Gatto’s ring, he said, except me. Jack Amaro was in the trucking business with two of Streaky’s crew, and they were making a lot of money. Streaky wanted to sit down. He wanted to bring this guy in because he was earning a lot of money. Giacomaro remembers that they met at Vesuvius in Newark. I mean, it sounds just like the Sopranos, doesn’t it? He described the table and how it went down. He said, Streaky sat at the head of the table with his sons right next to him, Joseph and Louis Jr. And his son-in-law, little Al Greco.

    [11:02] And Giacomaro remembered that Streaky was a skinny little guy who hardly said anything, but he said he had an ego big enough to suffocate the entire restaurant. Over again, little Al took care of the business during this lunch. He pitched Giacomaro on Friday. Him joining the family plan. And Streaky, during this time, he made a big production of putting some $100 bills between his knuckles. He held up his fist when the waiters came and they kissed his ring and took the bill and said, oh, thank you, Don Luigi. Thank you. During this lunch, he remembered that little Al once said, you know, we want to open the books for use. We got big plans for use. He knew what that meant. He knew he was then going to have to give him a percentage of his earnings and let them use his businesses to launder their money. Finally, he says, you know, Giacomaro says, I told Streaky and I told Lil Al, I said, you know, what can you really offer me with that? I don’t already have. He said, it was like everybody just quit breathing.

    [12:02] Just a dead silence fell over the table. He said he thought Streaky Yaddo was going to leap across his pastas and stab him in the eye with a fork. He didn’t, you know, he’s in a public place. And, you know, he would later say, you know, I was going to use them for everything they had, but never be one of them. You know, I’ll infiltrate their world all the way at the top if I can,

    [12:22] but I ain’t never being made because the only crime boss I want to answer to is myself. Joseph Gatto, Stricky Gatto’s son, was released in 1993, and he took over control of his father’s crew. He expanded the crew’s gambling operations and introduced, you know, brings it in the 21st century, so to speak, of the use of pagers and cell phones. And by 1999, he gets convicted again on some illegal gambling charges and took a plea deal. And at that time, he did admit that he was a capo of the Genovese family. You know, gambling is getting lesser, lighter sentences by then. He had a pretty light sentence. He gets released again in 2003. But a year later, he’s indicted in 2004 for running something called Catalina Sports, which is an offshore wire room in Costa rica bosley this thing was taking in 300 to 500 hundred thousand dollars profit per week and these gatos they were they were money earners that’s for sure that conviction gets overturned and you know by now 2005.

    [13:22] They did try him again in 2008. I don’t even know what happened. He’ll die in 2010. He’ll never go back to jail again. And nobody cares about gambling by then because it’s getting opened up all over the place. Streaky Gatto, who originally started talking about his father, died in prison in 2002. He never got out after he got that 65-year sentence from his RICO and murder convictions. So that’s a little bit about Louis Streaky Gatto.

    [13:48] And Carmine, thanks for suggesting that. So I hope y’all like this story. I hope y’all like my hat with my Gangland Wire logo on it. Talk to you later. Thanks, guys.
  • Gangland Wire

    Jerry Catena and the New Jersey Genovese Empire

    18.05.2026
    Retired Kansas City Police Intelligence Unit Detective Gary Jenkins sits down with returning guest Scott Deitch for a detailed exploration of one of the more understated yet influential figures in organized crime—Jerry Catena.

    Scott Deitch, known for his deep research and engaging storytelling, brings insight from his books Cigar City Mafia, Garden State Gangland, and his upcoming release Jersey Boss. The conversation moves from Tampa’s mob history to the inner workings of the Genovese crime family, with a focus on Catena’s calculated rise through the ranks.

    🔍 Episode Highlights

    Scott Deitch’s Mafia Journey Deitch outlines how he became one of the more respected voices in mafia history, driven by a fascination with overlooked mob figures and untold regional stories.

    Who Was Jerry Catena? A key but often underreported power broker, Catena rose during Prohibition-era influences and mentorship, eventually becoming a major figure within the Genovese hierarchy.

    Mob Influence in New Jersey & Tampa. The discussion connects Catena’s operations to broader organized crime networks stretching from Florida to the Northeast.

    Hollywood vs Reality. A look at how The Sopranos drew inspiration from real mob figures, including possible parallels to Catena and New Jersey crime families.

    Las Vegas & Gambling Operations. Catena’s involvement in early Las Vegas casino ventures reveals the mob’s hybrid model of legitimate business and illicit skimming operations.

    The Businessman Mobster. Unlike many of his contemporaries, Catena relied more on relationships and financial acumen than violence, aligning himself with figures like Frank Costello and Longy Zwillman.

    A Different Ending

    Catena’s relatively peaceful retirement contrasts sharply with the violent ends typical of organized crime figures.

    Personal Side of a Mob Figure

    Stories of Catena’s love for golf and generous personality add nuance to an otherwise complex criminal life.

    Tampa Mafia Tours Deitch shares details about his immersive mafia history tours in Tampa, offering listeners a chance to experience this world firsthand.

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    Transcript

    [0:00] Hey, welcome all you guys out there. It’s good to be back here in studio of Gangland Wire. I have one of my old friends here, one of my oldest friends in the podcast, Mafia podcast business. I interviewed Scott a long time ago. I went down to Tampa and went on his mob tour in Tampa. And we had a cigar before we went on the tour, and he’s got several really great mob books. So it’s Scott Deitch. It’s really great to have you back on the show, Scott. Yeah, it’s great to be back, Gary. And you missed the most important part of the Tampa trip was we made the bet on the Super Bowl. Oh, yeah. I had to send you something, didn’t I? You had to send me some Kansas City barbecue. Yeah, I had to send you some barbecue. I forgot all about that. Yeah. I’m like a Las Vegas gambler. I’m always talking about how much I won. I never come back and tell you how much I lost. Never notice that. Gamblers never talk about how much they lost.

    [0:59] So anyhow, Scott, you’ve got several mob books. You’ve been on the show before. Tell us a little bit about your background and the mob books that you have. I know you’ve got another one on the New Jersey mob. You’ve got one on the Purple Gang and a couple other things. You’ve got a Tampa book. So tell us about that and the titles of them. And guys, I’ll have the links to these books in the show notes. Yeah, so my first book came out in 2004, over 20 years ago. That was Cigar City Mafia, History of the Mafia in Tampa. I’ve written a book on Santo Traficante called The Silent Don. He was the last longtime boss of Tampa involved in CIA mafia plots and figures into some of the Kennedy assassination theories.

    [1:44] Garden State Gangland, like you mentioned, which is a first overall overarching

    [1:48] history of the mafia in New Jersey. I did Hitman, which is a look at the East Harlem Purple Gang. And then my upcoming one, among others, which is Jersey Boss, and that’ll be out in May of 2026.

    [2:04] Jersey Boss, the rise of Mafia power, Jerry Catena. Now, I’m going to get this question. Let’s talk about The Sopranos first. Let’s get that out of the way. Does this have anything to do with Sopranos? Was Tony Soprano based on this guy or somebody else that was connected to this guy, the Cavalcante family? So funny, because I was asked that a few years ago for the Star Ledger, the Jersey paper I grew up with. And there’s one of the guys that a lot of people point to as part of the inspiration for Tony Soprano was Tony Boy Boyardo, who was the son of Richie the Boot Boyardo. And Tony Boy was close with Jerry Catina. And in fact, Jerry Cattino was Tony’s, the best man at Tony Boy’s wedding. So Jerry Cattino himself is not really necessarily represented in the fictional universe of The Sopranos, but certainly people around there and this Tony Boy connection with some of the aspects of Tony Soprano are part of that. And he came up under Richie the Boot, Beardo. And Richie the Boot, he was immensely successful, financially successful. And Jerry Cattino was too. He must have learned well at reaching the boots, the foot at his knee.

    [3:17] Yeah. And even more so than Richie the Buddha was Longy’s Willman, Abner Longy’s Willman, who was really another major mentor to Jerry Catena. And really see as Jerry falls under the tutelage of Longy’s Willman during the prohibition era, he starts becoming more of a racketeer than a gangster. And that’s under Longy sees the value of legitimate businesses and investing. And in fact, I talk about it in the book, a lot of people don’t really know much about the New Jersey mob’s investments in Las Vegas. And Catena and Longy Zwellman started investing in Vegas in the late 40s. So, yeah, I think Catena was fortunate to have, or I say fortunate for him in his underworld career, to have mentors like Boyardo and especially Zwillman who steered him out of the purely criminal and showed him the value of the legitimate side of business.

    [4:14] The legitimate side of business with mafia rules. Absolutely. Yeah. I had somebody ask me, well, why don’t you go into business and do a podcast with one of these mobsters? I said, I’m not going to do business with a mobster. They got their own set of rules, and I don’t understand those rules.

    [4:31] I know the regular business rules, but I don’t understand those mafia rules. Jerry was, I see in some of my old notes here from way back, that he was close to Frank Costello, and that’s one of the ways that he got into gambling, and he was part of the Genovese family. So talk a little bit about those early days of Jerry Catena.

    [4:53] Yeah, so he’s born in Newark in Down Neck or the Ironbound neighborhood. Starts, I’d say, starts coming under law enforcement, screwing. He gets in trouble with the law around the prohibition era. He starts off as a truck driver, works his way up. He’s involved in illegal gambling at that time, then starts to get involved in the vending machine business. But he ends up becoming associated with members of the Genovese crime family. And along the way becomes very close friends with Frank Costello. After he’s made, oh my God, I’m drawing a blank, 46, he gets put under Willie Moretti’s crew. So he’s really becomes a core part of the New Jersey faction of the Genovese crime family. Interesting.

    [5:41] With that, I have to assume that he looked after their gambling interests down there as much as anything. Was that his initial focus, or was he more into extortion? No, gambling was definitely one of the—yeah, it was actually funny you mentioned hijacking. One of his earliest arrests was for hijacking trucks of cigarettes in the 1920s. Then he moves into illegal gambling.

    [6:07] He’s involved in bootlegging during Prohibition, but afterwards into illegal gambling. The other thing, he becomes very involved in the unions around the Port Elizabeth and the Newark Port area. And the interesting thing about Catena is even though he becomes associated with guys like Frank Costello and obviously Vito Genovese in the New York faction, he’s very much a New Jersey-based crime figure. So most of his operations are in New Jersey. Fort Lee, New Jersey at the time becomes a real hotbed of gambling. They have these nightclubs, places like Dukes. Jerry Coutinho becomes involved with that. Yeah, I would say it’s pretty accurate to say that illegal gambling was certainly one of kind of the primary revenue sources for him.

    [6:51] Yeah, and that’s more white collar crime. Now, he’s going to move on to going into legitimate business with the great A&P story, which is a great story. Whenever you’re ready, we’ve got to talk about that. Now, you mentioned about having the points in the casinos out there. We know that when Costello was shot, they pulled a piece of paper out of his, he had a piece of paper in his pocket that indicated what the take was on a particular day at the start. So was that, how did these guys from New York get into Las Vegas so early?

    [7:25] Longy’s woman starts going over to Vegas and probably, I think the connection there is Longy’s woman was close with Meyer Lansky. So Meyer Lansky, obviously out there with Bugsy Siegel, when they take over the Flamingo, the Billy Wilkerson deal, all that, then obviously Bugsy Siegel was killed. Meyer Lansky really gets his kind of foothold in at that time. Longy’s woman comes soon thereafter. after. And by the late 40s, early 50s, Jerry Catena’s there, involved in skim operations. And predominantly in the late 50s, after it opens, is the Fremont Hotel in downtown, which is still there on Fremont Street. It becomes really one of their major cash cows for Jerry Catena and his operations. And I’ll take a little segue here, because I think one of the really, interesting and important things about jerry Catena which differentiates him from a lot of the other mafia guys was he was very ingrained and embedded with jewish organized crime figures like long east women like abe green guys like that that are out of newark so his operations in vegas parallel a lot of the involvement of jewish gangsters in vegas as well so Catena really, takes a little bit of a different path than a lot of the traditional Mafio out of New York and New Jersey at that time.

    [8:50] What I find interesting, because like the Midwest mobs, they got into Vegas by guaranteeing getting these teamsters loans for non-Italians, front men, if you will, to build the casinos or make the existing casino bigger. But these early New York guys, I talked to an expert on that early development of Las Vegas. They said those farmers and ranchers in Las Vegas, they didn’t know how to run casinos. but the mob guys who’d had carpet joints, Frank Costello and Mayor Lansky and people like that, they knew how to run a casino. So those Jewish gamblers out of Cleveland, all those guys then moved out to help the farmers and ranchers that, that pull, had the strings of political power at the time and wanted to make money off the gambling and showed them how to run the casinos. Is that kind of how, would that be how they got in out there? Cause they weren’t guaranteeing teamsters loan at that point.

    [9:45] No. So yeah, you’re right about that too. And they’re bringing out that expertise of running these gambling operations in New York, New Jersey at that time. And it’s really the fortuitous timing as post-World War II, the tourism boom, Vegas starts booming, you get the entertainment, it all becomes this ecosystem that’s growing, keeps growing. And like you mentioned, later on when the Midwest guys come in, that’s when the Teamster Central Pension Fund, and they’re utilizing that. But so it’s interesting to see all the different ways that the mafia guys were moving in. There’s some other guys moving with the entertainment that comes over into Vegas as well. Yeah. Interesting.

    [10:22] So how did he, he didn’t just sit back and bring the money in. How active was he on the streets? Was he a street guy? If something needed to be done, would he go out and do it? Or did he hire somebody to do it? I guess would be my question. After Willie Moretti is killed, Jerry Catena takes over his crew.

    [10:44] That’s when he starts to become noticed not only in terms of respect and stature within the mafia, but law enforcement. He’s called in front of the Kefauver Commission in 1950. He’s called in front of the McClellan Commission in 59 again. And so as his star starts to rise in the 1950s, his friendship with Frank Costello, his relationship with Vito Genovese starts to grow. And in 1957, after Frank Costello is shot at, the famous shooting, The Majestic on the Upper West Side, that Vito Genovese becomes boss. He appoints Jerry Catena as underboss. And there’s a quote somewhere. I forget who was on a wiretap. And Genovese is there. I kind of wonder why Jerry was made underboss. And Genovese says something to the effect of this guy controls Las Vegas, meaning he’s a big earner. So he’s bringing in a lot of money to the family at that time. That’s when Coutinho’s stature really cements itself. Really? And I believe he was at Appalachian with Vito Genovese, too. Yeah, they’re in the same club. Which tells you right now his position in power.

    [11:54] Yeah, absolutely. Yeah, he stopped in the car. And I believe Bufalino was in the car as well with the same car. Oh, really? So he was a nationally known guy. By 1957, he was known all over the East Coast, for sure. And then in Las Vegas, too. So he was a mover and a shaker that kind of kept his head down, too. He’s not like Costello Genovese. He’s not exactly a household name. No. A lot of people don’t really know that name exactly. Yeah, and that’s why I wanted to do a book on him, because he’s a fascinating character, very influential, but not at the top 10 or 20 list of most mobsters. Generally, people know pop culture, and even in the mob world, he’s not as well-documented or as well-known. He must not have gone into New York and partied a lot.

    [12:43] He’s no John Gotti, was he? No, he did like nice restaurants in New York, but he stayed a little bit more under the radar, that’s for sure. Yeah. Interesting. Interesting. So tell us a little more about him. We’re up to 1957 and he’s got interest in the casinos. He’s been to Appalachian. He has solidified his position.

    [13:07] And we got that great A&P store extortion. What does he get into after that? There’s something else about the North American Chemical Company and detergent company that he’s muscled in on. So he becomes acting boss of the Genovese family after Vito goes to prison. That’s the argument I put forth in the book. And there’s a lot of evidence supporting that from wiretaps and stuff. He’s also getting much more involved in a lot of bigger legitimate businesses, gaming being one. But he starts investing in companies. One of these is this North American chemical company that you refer to. And they make this liquid detergent that is pretty caustic and not a lot of stores won’t carry it. So he’s trying to work with unions to pressure some of the major stores like A&P to carry this product.

    [13:59] Even though he’s the acting boss and he has a lot of close confidants and probably the closest Tommy Ebbely in terms of stature, although they don’t always get along. Jerry Catena really relies on his younger brother, Gene Catena. And he puts Gene in charge of this A&P thing. And rather than doing it the quiet way that Jerry likes it, Gene actually starts recruiting people to bomb A&P stores and actually results in the murder of a couple A&P managers of the stores that were refusing to stock this. And from a couple sources I spoke to, Jerry was pretty incensed about this and shooed his brother out pretty hard because this is out of character for kind of the way he was running things.

    [14:42] And then Gene dies in 1967 and the AP thing fizzles out after there. But I think it’s, yeah, because if you look at like the history of how Jerry does business, it’s very much an outlier in terms of just not only the outright

    [14:56] violence, but violence against people that aren’t involved in organized crime or the mob. What other business interests did he have over these years? I think probably one of the biggest that he gets into is Bally Gaming. And the name Bally, everyone knows the name Bally. It’s synonymous with gaming. They had their hands in fitness centers. They own Six Fleck and Bally’s still a big name, even though the Bally company now is basically Bally in name only, but let’s rewind back to the early sixties. Lee gaming becomes this really big manufacturer out of Chicago. It’s a subsidiary of Lion Manufacturing. And the owner of Lion Manufacturing dies suddenly from a heart attack.

    [15:36] And the company goes into a trust, a bank trust. But there’s a salesman in their Chicago office named Bill O’Donnell. And he sees the value in the Bally name. So he puts together an investment consortium to buy Bally. And he goes to his biggest distributor, which is a company called Runyon. And Runyon’s based out of Newark. And the three primary owners of Runyon are Barney Sugarman, Abe Green, who grew up one of Longy’s Women’s top men, and Jerry Catena. And Jerry was very involved in the day-to-day business of Runyon. So Jerry puts together an even bigger pool of investors, and they basically buy Bally. And this coincides with the introduction of an electronic version of a slot machine that Bally was manufacturing. Oh, really? So Bally really starts to take off. And the interesting thing about this, again, there’s not one other mafia guy in this investment group. Nobody from the Genovese family, no Italians. It’s a bunch of old Jewish gangsters and other affiliates that Jerry puts together for this investment. And one of the interesting things is as Bally becomes bigger in the 1960s, Jerry just starts making more and more money. You can see on wiretaps that he doesn’t really want to be boss anymore.

    [17:01] He’s really into golf. He just wants to not be boss anymore. But anyway, he’s involved in Bally. He sells his shares in the mid-60s because Bally goes public. But there’s an enormous amount of information showing that he basically sold his shares. But Abe Green and some others bought additional shares that were really Jerry. So he stole it as his hands in Bally.

    [17:27] Valley. Interesting. He’s one of those guys. I met this wet guy once. He had an auto theft ring. And I said, dude, if you would take your skills, your organizational building, your brains and put it into a regular business, you’d do all right. So Jerry’s one of those guys, isn’t he? Yeah, for sure. If he put all his enthusiasm and expertise and organizational

    [17:48] abilities into regular business, then he’d do okay anyhow. And one other thing during this time too, he still stills his illegal operations going he still has the skim and he was getting forty two thousand dollars a month in the early 60s out of the skin for himself person that’s a lot of money and that’s not counting all the other stuff and one of the other interesting things that i found out through researching this is he did not take kick nobody had to kick money up to him he was self-sufficient he let everyone keep their own stuff so he unless he was involved in it he never took an envelope from his other ones, because he didn’t really need to. He had so much of his own stuff going on. So it’s another kind of interesting little detail. Yeah, he was a much-beloved boss. He probably saved himself a lot of trouble by not getting greedy. Yeah, and it’s funny, because he was very aloof, like I said. He didn’t necessarily want to be boss. And you hear on wiretaps, like.

    [18:46] Shift to carload and people timey ebbly just complaining about him they’re like this guy’s really aloof he’s not in touch you can’t get to see him this but yet nobody tries to make a move against him because i think even though he probably wasn’t the most ideal boss in their eyes in terms of being hands-on they realize they he’s doing okay he was very well respected and well liked and i think that went a long way huh interesting that which which makes me wonder what uh how did And where was Vincent Gigante during these years as he’s slowly but surely moving up? He must be eventually getting come up in right behind, under Catena. Yeah, so Gigante’s in New York at that time. Tommy Eboli’s, like the head, oversees a lot of the New York operations. You have Benny Squint Lombardo, who’s powerhouse behind the scenes. And then Genovese dies in 69.

    [19:44] Catena takes over for a very brief period but he actually goes to prison in 1970 and not from being convicted of any crime he gets sentenced to prison for contempt because he gets brought before the New Jersey State Commission of Investigation and he refuses to testify, and they jail him for contempt for almost five years Five years? Wow Yeah, in fact it’s one of the longest sentences ever imposed on someone for contempt and he’s ultimately freed by the Supreme Court You can look up, there’s a Supreme Court decision. It’s Catena versus something. I have it in the book. But yeah, so when Catena goes to prison, then the Genovese leadership continues moving forward. Emily’s killed in 72, and then Gigantes starts showing up in the picture by then.

    [20:29] Yeah, and he’ll move on up. So how did Jerry then, he’s done five years in the pen. Man, now what happens after he comes back out? Is he assuming he’s placed or does he start easing himself out? Use that as an excuse to get on out. Exactly. You nailed it on the head. Yeah, within less than a year, he sells his home in New Jersey. He already owns a place in Boca Raton. So he goes to Boca and really starts fading back playing golf, but he still keeps his, I don’t want to say consigliere because he’s not considered the official consigliere at that point, but he’s still very involved and people have want, want to come for advice or guidance. They’re meeting with Jerry. He’s seen meeting with like Sam The Plumber, the Calvo Conte, and these other guys. And one kind of weird thing, in 1983, there’s a series of both federal and New Jersey State police, the org charts that you see. And Catena’s considered a consigliere at that point, but he’s probably at that point semi-retired. And by the mid 80s, he’s completely retired and steps back from business.

    [21:43] Interesting. And he lives basically one of the few bosses that just retires on his own accord. Yeah. He didn’t retire into the penitentiary. He had never really come out until he couldn’t really do anything when he came back out. A lot of them ended up like that. Either that or dead some way, one way or the other. And boy, he came up through the growth, the huge growth of the mob up 50s into the 70s in the New York families especially. They really exerted a lot of power and grew during those years. So he saw it all, didn’t he? Yeah, he was born in 1902. So, you know, by the time he’s a teenager in his 20s, Prohibition starts. So he’s right there.

    [22:28] You know, when he turns 18, Prohibition starts. He’s right there through his adult life. And he lives a long life. He dies in 2000 at 98 years old in Punta Gorda, Florida.

    [22:39] And pretty much his reign in his life is the 20th century. He pretty much bookends the 20th century. So you’re right. When he hits his prime, his 40s, 50s, that’s when the mafia is hitting their prime. They hit their prime with the political contacts and the concrete club and all the construction in Manhattan. They’re all making so much money. You mentioned political context. That’s another thing, especially in the 50s and 60s, is Catena is very politically astute. And the Genevieve’s family themselves, they’re tied in with the mayor of Newark, the police chief. They have a state assembly or state representatives on their payroll. He’s on wiretap or his associates talking about these politicians they have in their pockets. So he certainly played the political game as well. In your research, did you run across anything that kind of got his take on the purported meeting in, I believe, in Philadelphia between Chicago and New York or East Coast guys where they agreed to divide up Las Vegas for Chicago and Atlantic City for the East Coast?

    [23:47] No, because by the time that he got out, Atlantic City just started. He was fading away. But here’s an interesting thing, though. His name really starts popping back up in the papers around 1977 when Atlantic City legalizes gambling. The reason for that is because Bally makes a bid to be one of the early casinos. And there’s a whole bunch of hearings that Catena’s name has brought up in relation to his previous ownership of Bally. And what’s interesting is that up until the mid nineties. And again, Catena is long retired. He’s in his mid nineties. Every time Bali reapplies for their casino license, Atlantic city, there is a line in there. And I pulled it from the gaming control board that says Bali is not allowed to give any payments to any companies owned by Jerry Catena or blah, blah, blah. So even though he’s long retired, he’s towards the end of his life. They’re still wanting to keep Jerry Catena out of Bali gaming.

    [24:46] I have a long memory there in New Jersey. Yeah. When they were getting ready to do the casino thing, we happened to have a, what we called a LEIU, Law Enforcement Intelligence Units, Bi-Zone Conference. And what that meant was the Eastern Zone and Central Zone met. They met in Kansas City and a whole lot of New Jersey state troopers and a couple of guys from the, whatever the county is there, Atlantic City, from the prosecutor’s office. And a couple other intelligence people, they were like telling us all those precautions that they were taking trying to keep the mob out. They were really working like hell to keep the mob out. And they really never exactly got it done. And I remember talking about that even the mob will get an interest in… Transportation companies that bring people from New York. Yeah.

    [25:38] The gambling junkets were a big business. And to that point down here in Tampa, the Tampa guys had junkets out to Vegas. Same thing as they weren’t involved in Vegas, but they control these businesses and were bringing gamblers out there and taking a little off the top. Yeah, we had a junket out of Kansas City, and that was the guy that ran the junket. That was the guy that was bringing the skim back from the Tropicana. Oh, okay. Yeah, yeah. So that was the cover they used. he, they called him the singer. He had a reason to go back and forth to Las Vegas. And they talked about that, how nobody paid any attention to him because he already had a reason to go back and forth. Oh yeah, that makes sense. That’s smart. As you guys, they think about it, but I have to think about everything because they got a big brother breathing down their neck.

    [26:24] Absolutely. Scott, you got any other stories that you want to tell guys about it that are in the book and Tyson to go get that book? Yeah. So just a couple other random things that I found really interesting.

    [26:36] Jerry Catena’s name was in the newspaper a lot in the 1950s, but not for any kind of mob stuff. He was an avid amateur golfer, and he actually golfed in a lot of prestigious tournaments around New Jersey and then later in Florida. And then a couple of people I spoke to, one guy remembers being a caddy for him and saying how Jerry was a very good tipper or tip him with 20, 50 bucks back then. That was huge. A lot. Yeah. But he spent about as much time in the golf course as he did doing mod business. He was all the way up in, you know, up until his eighties, he was a avid golfer, which I thought that was interesting thing.

    [27:13] Yeah. The other thing, too, is really just how he shows up in these little different pockets of mob history a little bit behind the scenes. And I think the other really interesting thing about Jerry Catena is he was a very soft-spoken, everyone I talked to, people that knew him, family, his old attorney, never raised his voice, never lost his temper, very low-key, very… And it was funny, he’s a Neapolitan heritage, which a lot of the Genovese guys were. But if you look at pictures of him, he looks Irish because he had really light hair and blue eyes. So he looked like a stereotypical Irish priest in some photos of him. But yeah, he definitely was cut from a different cloth, I would say,

    [27:57] of most of those mob guys, for sure. Certainly, I think if you were to pick a family for him to be in would be the Genovese family, because they always seem to have more of those racketeers rather than gangsters, whether it was Frank Costello or Luciano or whatever. Yeah, interesting. No Joey Gallows in there. No, yeah, no.

    [28:19] Like the Columbos. All right, Scott DeGay, it’s really been great having you on. It’s an interesting book, and I’ll have links to all your books down in the show notes, guys. You might want to get that Garden State Gangland. Garden State Gangland, yep. Garden State Gangland to give you the bigger picture about New Jersey boffy stuff, as well as more of a narrow view of it with the Jerry Catina book. So I really appreciate you coming on the show. Oh, one other thing I forgot to mention, and Scott and I talked about this when we first got on, is he does a mob tour of Tampa all winter long. So you guys from up north that go down to Tampa or go to Florida over the winter, you need to go down there and take that tour. I actually have an example of the tour on my YouTube page. You have to go up there and maybe search on my YouTube channel for Tampa tour. And I think you can find it so you can see what you’re getting into. Yeah. Yeah. Tampa Mafia tours. We do them generally September to end of April. In fact, we’re recording this towards the end of April when we have our final tours. Nobody wants to be walking around outside in August. I can testify. It’s a great tour. It was a lot of fun. Thank you. Appreciate it. It’s a good thing to do in the winter too. Yeah. For when you’re up north. All right, Scott, thanks so much. Thanks again, Gary. Always a pleasure being on.
  • Gangland Wire

    Boston’s Mafia Rackets, IRS Wars, and Mob Secrets

    11.05.2026 | 28 Min.
    In this episode of Gangland Wire, retired Kansas City Police Intelligence Unit detective Gary Jenkins interviews Eddie Inserra about the Boston Mafia. He is the author of Confidence of the Mob: The IRS Agent Who Took down the Mob – Then Advised Them, a deeply researched account of his grandfather, Fred G. Pastore, a key figure in early IRS efforts to dismantle organized crime.

    Fred Pastore was part of the IRS’s early “racket squad,” targeting Boston Mafia enterprises. His work paralleled the groundbreaking financial investigations that helped bring down figures like Al Capone, demonstrating how financial crimes could succeed where traditional policing struggled. Then, he leaves the IRS and advises the Boston Mafia.

    Eddie recounts how he uncovered his grandfather’s story through a remarkable archive of family documents, photos, and recordings. These materials revealed a complicated dual life: Fred was both a relentless investigator and, later, a trusted confidant to certain Boston Mafia figures. This paradox sits at the center of the book and this conversation.

    A major focus of the discussion is the “pinball racket”—a widespread illegal gambling operation hidden in plain sight within bars and storefronts. Fred’s investigations exposed how these machines generated significant underground revenue streams for organized crime, particularly in Boston. Eddie details the innovative and often risky techniques the IRS used to infiltrate these operations, including undercover work within corporations like Raytheon, where illegal gambling rings had taken root among employees.

    The episode also explores the institutional challenges Fred faced. His aggressive tactics and unconventional relationships eventually brought him into conflict with IRS leadership and political figures, forcing his resignation.

    In a striking turn, Fred leveraged his deep knowledge of organized crime to advise former mob associates—highlighting the blurred moral boundaries that often exist in this world.   Eddie adds a personal dimension, sharing memories of growing up around his grandfather and describing the cultural landscape of Boston’s North End, where family, community, and organized crime often intersected.

    These stories provide insight into how relationships between law enforcement and mob figures could be shaped by proximity, respect, and shared environments.  The conversation concludes with a look ahead at Eddie’s upcoming podcast, which will expand on these themes through interviews with former IRS agents, mob associates, and others connected to Fred Pastore’s extraordinary life.   This episode offers a rare look at the gray areas of justice—where the line between hunter and ally becomes increasingly difficult to define.

    Check out the book: Confidence of the Mob: The IRS Agent Who Took down the Mob – Then Advised Them,

    Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire

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    To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here

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    Gary Jenkins: [00:00:00] hey, are you wire tapers? Good to be back here in the studio. Gangland wire. This is Gary Jenkins, retired Kansas City Police Intelligence Unit Detective. Glad to be back in the studio. I have a man on the line who’s written a really interesting book called Confidence of the Mob, the RIRS agent who took down the mafia and then advised him.

    So that’s what’s interesting about this. Here’s a man. The, it was part of the early racket squad with the IRS intelligence who were the guys that went after the mafia and in all the different cities, most famously in Chicago, and took down Al Capone, and he ends up in a conflict with his bosses over informant and then.

    He goes into business as an accountant and ends up advising Jerry Angelo and some and childhood friends, really. ’cause he grew up in the north end of Boston. So this is his grandson Eddie and Sarah. Welcome Eddie.

    Eddy Inserra: Hey, thanks Gary. Glad to be here.

    Gary Jenkins: All right guys. Now there’s the book and I’ll have [00:01:00] links to it in the, the show notes as well as you can see the book over Eddie’s right hand shoulder there. You’ll get it. Now. First thing I wanna bring up about this book, Eddie, is I’m gonna ask you a little bit about how you got into this, but about this QR code you have in there, guys, there’s a QR code in there.

    I don’t know, about a quarter of the way in. Tell us about that and what was your idea to do there?

    Eddy Inserra: Yeah, so the QR code takes you to our website, which is it links to confidence of the mob.com. And this project started off as me interviewing a bunch of people about. My grandfather’s story. So I have all these audio clips, I have all these documents that I found in the box that my mother gave me that really had my grandfather’s complete career in there.

    So it’s more of a evidence-based website where if you scan that QR code, you can access some of the documents. Listen to some of the clips by the book, just learn more about the story overall. So it’s, the QR code is meant to be interactive, so you can take from what’s on the book into your phone and just explore more, [00:02:00] right?

    Gary Jenkins: Really interesting that with the new internet and you can do so much more and make your, what used to be just a hardcover. Paperback or hardcover piece of, a bunch of papers together and you can go onto the internet and you can find so much more with really not that much effort and a little bit of effort on your part.

    I know that I did something like that with a book I did. And it is a little bit of effort, but it’s not as much effort as is really, I think for that to further instruct people, teach people what that life was like for your subject. ’cause that’s what you’re trying to do, is you wanna tell people what.

    Your grandfather’s life was like, and so that’s I think it was just ingenious of you to doing that. I haven’t really seen that. I don’t think there’s probably other books that I didn’t notice, but I had not seen that before. Anyhow Eddie, let’s let’s go back. You’re the grandson.

    Fred g Pastor, tell us how you got into this, your earliest memories of this. Did you know your grandfather when you were a little kid and probably didn’t get the stories you wish you’d gotten? More than likely [00:03:00] I’d have him. But tell us a little bit about that.

    Eddy Inserra: Yeah, so he actually passed away when I was eight years old, so I got to know him for eight years.

    He passed away in 1988, and then, I knew my grandfather was always, when you see your grandfather, he is always happy when you’re, a little kid. One side of him, always happy, generous smile on his face, always laughing. Typical grandfather give you candy when no one’s looking.

    Things like that. So typical grandfather, I found out later on that his life was much more complex than I had thought. And when I was younger, he had an office. So I’d go into the office and I’d, everybody would be doing accounting work. He’d have probably about, he had about six or seven employees, maybe more at some, sometimes I’d go into the office and I’m just a kid running around the hallways and sitting at the desks.

    My father worked there as well. And yeah, I’m just watching them push papers and write down numbers and stuff like that. So I didn’t think it was too, I thought it was pretty boring. It was cool, but it was boring. But later I found out much more about him.

    Gary Jenkins: Interesting.

    Eddy Inserra: Yeah.

    Gary Jenkins: So later on in life, how did you stumble [00:04:00] across this whole dualistic life He had in a way I would maybe dualistic not at the same time but these two careers that he had how did you stumble across that?

    Eddy Inserra: There was a box that my mother had in her attic, and it was a, an old Florida citrus oranges box carton and overflowing with papers. And she, about 10 to 12 years ago, she gave it to me and said, Eddie, I want to give you these documents that your grandfather’s documents. I don’t know what’s in them, but there yours now.

    So I said, okay, great. And I pulled out a couple of documents and I looked at them. One was like an accounting ledger. E exactly what I expected. Some, some numbers and things like that. And I put ’em back in the box and I said, lemme put this on the shelf and I’ll take a look at the other documents some other time.

    So a couple weeks later, I go back into it and I pull out some papers and I start seeing profiles for big names and organized crime that I had heard of in the past. Jerry Angiulo, Raymond Patriarchal profiles on Racketeers Bernie [00:05:00] McGarry, doc Gansky, all these huge. Folklore names from Boston gambling and numbers and mafia times from the 1950s to the 1960s.

    I started piecing it together and I said and then I find a telegram in there to, to the White House Bobby Kennedy and JFK from my grandfather saying, I need to meet you at the White House right away regarding this Bernard Goldfine case that I’m working on. And I just started piecing this together and I said whoa.

    I never knew anything about the IRS side, but. He was really the tip of the spear. You mentioned like Elliot Ness, Al Capone earlier. It was the same sort of division, the intelligence division that he was working in, but he was in the Northeast District and it was, this was obviously after Capone that era, but next generation of, racket squad leaders, and he was the tip of the spear in Boston and the FBI didn’t have jurisdiction at that time to go after these racketeers.

    It was the IRS at that time. Later on, after he switched sides, so to say the FBI took over, but at that time, the IRS was the [00:06:00] potent weapon against these racketeers. So I’ve got all his documentation on investigations, case notes commendations it’s just really a treasure trove of, his whole career.

    And I pieced this together over years. There’s hundreds of documents, had to put a timeline together.

    Gary Jenkins: Really.

    Eddy Inserra: You’ve done investigative work, you know how that stuff works and I didn’t know anything about it, so it was just complete disorganized mess and had to pull it all together. Yeah.

    Gary Jenkins: The first thing you have to do is get a timeline.

    Eddy Inserra: Yeah.

    Gary Jenkins: That is paramount. When you’re doing something like that, you have to get a time. In order to keep things straight. Otherwise, it just becomes a, it’s just, you can never get it straight in your mind. Interesting. You know that the IRS back in the day was the premier organization that, that and the the the Federal Narcotics people were the ones that went after the mafia, whereas the FBI wasn’t, and you know what people don’t understand about the IRS many people, the IRS is just this big, huge. Organization that’ll come down on you when you [00:07:00] cheat on your taxes. But it’s really two divisions. There’s a civil division, but then there’s this criminal division, which was called the Intelligence Unit for a long time.

    And then I think your grandfather what I read in your book was he went into some special squad within the intelligence division called the Racket Squad. Is that right?

    Eddy Inserra: Yeah, that’s correct. The Racket squad was a specialized division inside of the Intelligence Division. Okay.

    Which only went after high profile Racketeers. And there was even an old TV show if you go on YouTube and look up Racket Squad. Yeah. There was a TV show about that. Yeah.

    Gary Jenkins: I remembered. I think no, it was gangbusters on the radio, but Racket Squad was on tv. Interesting.

    Eddy Inserra: Yeah.

    Gary Jenkins: So he grew up with a lot of the mobsters in the Boston area.

    Correct.

    Eddy Inserra: Correct. He was born in 1919, the same year as Jerry Angiulo. They were the same age which you’ll hear that name a lot and a lot of your listeners know. Jerry Angiulo was the under boss of Raymond Patriarch in Boston. And so they grew up right across through the bridge.

    [00:08:00] So Fred grew up actually in East Boston and Jerry grew up in the North end, and I confirmed that they did know each other when they were kids. I don’t know how deep that relationship went, but they did know each other when they were kids. And there was another man who ended up becoming partners with Fred later on in his post IRS career who he grew up with named Guy Spano.

    And he was also in East Boston at that time, and they were all this they knew each other,

    Gary Jenkins: interesting. Fred, knowing all these people, he knows about the bars and stuff and I noticed one of the things that was interesting, one of the things looked like early cases.

    He went after the pinball racket. Guys back in the day, every corner store bars, they all had pinball machines and they were a great way. To launder money and get all this cash money in and not pay their taxes on kinda like a cover charge that strip clubs get today. Whether there’s a way to, to get line cash money in that didn’t really go through the cash register.

    Tell us about that pinball racket.

    Eddy Inserra: Yeah, the pinball racket was a big deal back then. There was a lot of paperwork in [00:09:00] his box about that. There was a map that he had inside that box that showed all the different places he was raiding in Massachusetts just for the pinball machine. Pinball machines and the pinball machines back then were a game, not a game of skill because they didn’t have flippers on them.

    So the flippers that, that came on later, then it became a game of skill and it wasn’t actually just throwing your money away and gambling, so to say. So they weren’t able to go after them after they added flippers to the machines. But before the flippers interesting.

    Gary Jenkins: Yeah, I did, I didn’t really realize that I saw one of those when I was.

    You my late teens over in Kansas City, Kansas, and now I didn’t really realize what the deal was. What it was if you play it so much and get lucky and your ball goes to a certain place, then you win. But if it doesn’t and there’s no way to have it, is all pure luck. That’s the difference.

    I’ll be darned. I never thought about that. Interesting.

    Eddy Inserra: Yeah.

    Gary Jenkins: Of course from then, that’s gambling and that’s where the money is. So he [00:10:00] continues on going after mobsters, Italian mobsters in that area of the country in organized, more organized gambling. So tell us a few of his other organized gambling investigations.

    Eddy Inserra: Yeah, he went after the Italians. He also did go after a lot of the Irish too that in his paperwork too. Wimpy Bennett, Walter Wimpy Bennett. There was a lot of, in Jewish DKI, like I mentioned. Yeah, a couple other too but yeah, one, one big investigation that really put him on the map was.

    The Raytheon investigation. Raytheon we know as a big defense company and they’re headquartered in Massachusetts. They always have been, I don’t know if they still are, but they have been up until a few years ago. But huge corporation and during that time was the Cold War. So they’re supposed to be building missiles, but they called the IRS saying, Hey, listen, we’ve got a problem.

    Our production, our manufacturing floor, everybody’s supposed to be working, but. They’re all not on the floor and they’re gambling somewhere. We don’t know where, we don’t know the root cause of this syndicate, but it’s in all of our buildings and people are consuming their time, playing the [00:11:00] daily numbers, betting on sports, all kinds of stuff.

    And they couldn’t really get to the root of it to root it out of the system. So they called the IRS, they assigned Fred, my grandfather to the case, and he took the lead. He ended up sending a bunch of his agents in undercover as janitors, and they had to go through the whole process, the whole hiring process as a normal, employee would try to get hired.

    So they’d have to submit an application, go through the test, all that stuff. Because the, it was just so embedded in Ray Raytheon that someone would. Tipped them off. So he got a bunch of these janitors in and they ended up finding out that the, there was long lines going to the bathroom all day long.

    And that’s, they were making the bets, taking the bets in the bathroom stalls in multiple locations. They rated them all at the simultaneously and they got a bunch of leads after that for more mafia stuff, but it was a big mafia gambling syndicate embedded in the US government sort of defense contractor.

    So that got him, that was on the cover of the newspapers. It was in. Magazines. It was a big deal. [00:12:00] So

    Gary Jenkins: Interesting. After that is that he gets crossways with. His bosses and with the US attorney’s office eventually. Was there any other cases I see on the headline here, Pastore names Paul’s, me and politicians behind the bookies.

    So how did he get into to finding who the bookies were paying off?

    Eddy Inserra: So he, he had an undercover confidential informant, I should say, who was giving him a lot of information. And we were real in the book. Who that was, we didn’t know at the time. Nobody in my family knew until a few years ago, and that’s, we’re talking 60, 50, 60 years ago.

    And even the president and RFK at the time wanted to know his confidential informant. So Fred was getting some really good information. They didn’t know where it was coming from. And Fred had made a deal at the time with Eisenhower and the chief of the IRS that. He’d keep this confidential informant on his, on the payroll, but the only people that would know about it was Eisenhower, the chief of the [00:13:00] IRS under Eisenhower and Fred.

    And then JFK came in, RFK came in as the Attorney General and they wanted to know whose confidential informant was and he would never give him up. So that, that caused some tension between Fred and RFK. Before that there was another case. With a man called Frank Aya. I don’t know if you’ve heard of him, but he’s out, he was out of Worcester part of the, actually, gen Outta Worcester.

    Yeah, outta

    Gary Jenkins: Worcester. Okay.

    Eddy Inserra: Yeah. Part of the Genovese faction so New York, but I, their territory went all the way up to Worcester. And the FBI was actually investigating him for the Brinks robbery in Boston.

    Gary Jenkins: Oh,

    Eddy Inserra: really? At the time. So they were looking for leads because they had understood that one of the guys was from Worcester.

    They’re, they assumed so they went interrogating him, and he said no, I’m not a criminal. I’m just a bookmaker. And as soon as he said that I guess Hoover didn’t want anything to do with Bookmaking at the FBI. So they just threw their hands up and they threw it at the IRS and [00:14:00] that fell in my grandfather’s lap.

    And so he started digging into IAC and he, he actually built a case against him. He ended up going to jail. But during that process, when he was investigating Ioni, Ioni gave up another man. His name was Bernard Goldfine. Wasn’t in the mafia. He’s a big businessman. He owned all these textile manufacturing companies.

    And he kept getting the contracts for all the US government, military uniforms every year. So no one else would ever win. And my grandfather exposed that there was some bribery and corruption going on. Between him and Eisenhower’s chief of staff named Sherman Adams.

    Gary Jenkins: Yeah,

    Eddy Inserra: I

    Gary Jenkins: remember, I remember that.

    Sherman Adams he went down. I remember that.

    Eddy Inserra: Do you remember the Una coat? That’s what that was the big

    Gary Jenkins: thing. Yeah. I forgotten about that. Somebody gave me this Una coat. I never was sure what a Una coat was, but yeah, I forgotten about that. The Vicuna code and he and everything, they found all these papers that be.

    For Eisenhower to four eight C, it’d have to say [00:15:00] KSA Sherman Adams. That was a big deal. While he was spooning feeding Eisenhower all the, anything that he wanted to have.

    Eddy Inserra: Yeah. That’s funny you remember that because that’s, yeah.

    Gary Jenkins: Yeah. That was huge at the time in the fifties.

    Eddy Inserra: Yeah. For some reason, he bribed him with a lot of things, hotel rooms, cash, all these things.

    But the Vicuna code, for some reason, stuck in the media, and that was my grandfather’s work, was exposing that and yeah. That was a big deal at the time and after he exposed that and with him not giving up that confidential informant. RFK wanted Fred out of Massachusetts.

    Pretty much out of the cross heads. We can get into that if you want, but yeah that’s the next

    Gary Jenkins: thing. What would he want? We, because Kennedy’s of course, were Boston area, new England based, and a lot of their people probably could then get in trouble with because of Fred Pastore and his bulldog attitude towards enforcing the law.

    Was that the deal?

    Eddy Inserra: Yeah, Fred would follow the money. I know that’s a common thing, but he really would follow the money. And from what I [00:16:00] understand, I wasn’t there, I didn’t live at that time, but from what I understand, he followed the money and wherever it led him and that led him right up to the White House.

    You know how politics are there, it’s a dirty game. So I’m sure that might’ve been someone who gave money to the candidate, maybe even the same guy, Bernard Goldfine or somebody. And if Fred dug that up, they could get. The same treatment Sherman Adams did.

    Gary Jenkins: Yeah. Yeah.

    Eddy Inserra: They wanted Fred out of there.

    Yeah.

    Gary Jenkins: So what happened then? They it seemed like they, they repressed him to reveal his informant or something like and he ended up, either I quit or, I have to give up my informant. Is that, was that what it came down to? Hobson’s choice like that?

    Eddy Inserra: Yeah, it came down to that. They tried to actually reassign him to Syracuse. New York was really, it was a demotion in pay and in actually title as well. So he would’ve been brought down. He wouldn’t have been in the rack racket squad. He would’ve been down to a special agent again, and would’ve been a step backwards and they would’ve had him out of the mix in Boston.

    And that’s really what they wanted to accomplish is silence Fred. Yeah. [00:17:00] So he was faced with a decision, do I take that demotion and that’s the end of it, or. Do what he actually did, which was, took him back to his up upbringing in East Boston. Tough poor kid when you actually have to face the bully, I think.

    And that street grit that he actually said no. You know what? He held his own press conference in downtown Boston and he said, I’m resigning from the IRS today. And I’m opening up my own tax fraud defense firm right across the street. He wanted to view them out the window every day. He had a chip on his shoulder.

    And so he ended up advising the same kind of people and some of the same people that he was previously going after at the IRS. And he was like a super weapon for those guys because he knew all the legalities and the loopholes and how to structure your businesses and things like that.

    So

    Gary Jenkins: yeah, I noticed there was like a Fred Angiulo was that Jerry’s brother then.

    Eddy Inserra: I don’t know if there was a Fred, if there

    was

    Gary Jenkins: a wonder. I thought it, it was Fred. I may have got [00:18:00] that name wrong, Nick in the Nick in my head, because your dad, your grandpa’s name was Fred Pastor. But anyhow, there he defended Angiulo and some of their people, he, he knew everybody went to North End at eight and, they were socially compatible, if you will.

    So tell us a little bit about that, what you learned about those, that part of his life.

    Eddy Inserra: Obviously post IRS career, I learned that from my mother and other people, that on the weekends Fred would go on Friday night. Him and his his daughter whose youngest daughter is Charmin, which is my mother.

    Oldest daughter’s, Pam and my grandmother is Nina. And they would go into Boston to the north end and they’d go down there for, to go to the bakery sit out front. The women would sit out front eating pastry, and Fred would go out back for about 15 minutes and. To me it was him giving advice maybe face to face.

    To, to Jerry and he’d come out 15 minutes with a paper bag from what I’ve heard. And and that would be it. Then they’d go to the fruit market and then they’d go home and they’d go out to Stella’s. [00:19:00] Restaurant in the North End on Fleet Street at the time, which is a famous spot.

    Even, JFK, they used to go there. But it was a real famous spot. Fred would be there a lot with the family. And on the weekends my mother remembers. So the Injus, by the way, Jerry and Jula, there was five brothers who really ran their empire together. But Jerry was the head of it and the genius with numbers.

    And he shared that with Fred. They both had a genius with numbers. So that was some that was interesting. And Nick would, his brother Nick would go to Fred’s house on Sundays, and my mother would call him Uncle Nick. He’d always bring something. One time he brought a pet dog for them. They had a dog, and he’d bring all kinds of gifts and they always saw the nice side to these people.

    Even in the office, when I went to the office and I met a couple of these people when I was young, I didn’t know who they were, but I, you’d always see the nice side because.

    Gary Jenkins: Yeah,

    Eddy Inserra: Fred was the golden goose helping them keep their money, but most importantly keeping them outta jail. So

    Gary Jenkins: interesting.

    Huh? That’s a, that’s quite a career switch. [00:20:00] The were you in 98 Prince Street? The famous 98 Prince Street. I went to the north end, went around, took some pictures and stuff. It’s nothing like it, it’s described, but back in the day, other than, it’s really cool, those little narrow brick streets and restaurants and everything.

    Talk about the north end over there.

    Eddy Inserra: The north end is that’s the Italian enclave of the city. Boston has different enclaves, different cultural enclaves I should say. And the North end is the the Italian, it actually was the was the Irish before the Italian. So a lot of people don’t know that.

    But I didn’t know that. The Italian section, and that’s where there’s, world class Italian food restaurants, every 10 feet. And. It’s a tight knit community. Everybody knows everybody especially back then. So you walk down the street, you’ll see people hanging on the corner and if when you’re, when you were a kid you’d go get your fireworks there at the park and, illegal fireworks and get whatever you want.

    But yeah, 98 Prince Street was where Jerry ran his sort of headquarters out of there and they called it the doghouse. That was, [00:21:00] they knew they had eyes looking out for them as well being there. So the whole neighborhood was really looking out for them. And eventually the FBI caught them by wiretapping a vehicle up front.

    Yeah. So inside. But yeah, it’s really tight knit Italian. If you come to Boston, I really recommend you go, especially if you want to eat some nice food and see how this still some remnants of how it used to be, like you said, those brick roads and things like that. It’s pretty nostalgic and interesting.

    Gary Jenkins: Yeah. Yeah, it’s really cool. I’d highly recommend any of you guys. You go out to, you, go to Boston, go to the north end and eat and just walk around. It’s really nice, although it’s pretty busy on the weekends, so a lot of people down there, man and some of the restaurants, there were long lines to get into ’em around dinnertime.

    Eddy Inserra: Yeah, try if you can make a reservation, try to, if not.

    Gary Jenkins: Yeah. Yeah. Good bakeries too that the nicer places. I can’t even remember the names of ’em now. I had ’em that day. But anyhow, so I have to, I’m gonna flip back just a little bit. I made a jotted down a note [00:22:00] about Frank, the cheese man c Chiara, who was at Apple Lake.

    He did he who was the consigliere, I think for Patri arca. I believe your grandfather went after him or had some dealings with him. Do you remember that?

    Eddy Inserra: Yeah, he, there was some documents in the box about him and they were telling him he was definitely the concierge for arraignment at the time.

    And there were documents that Fred’s team was actually tracking him. They were watching him, he was going to Cuba back and forth to Cuba at that time. And so they thought he was moving money or just setting things up with a casino and things like that down there. They couldn’t, I don’t know if they actually got him to go to jail.

    I don’t remember if they were able to prosecute him, but they were checking him at the airport. I remember they checked his passport. But he was the, he was a money man as well, so he was known to be like the bank at that time.

    Gary Jenkins: Did did your grandfather have any trouble?

    His own troubles with the IRS af? Did they come after him or try to go after him at any point in time? Later in his career? Usually they [00:23:00] do. Yeah. They could be pretty vindictive. I’ve seen it here where an FBI agent then becomes a white collar crime lawyer. And boy, I tell you what, his old buddies, he was, they, he, a friend of mine went like that and he was surprised.

    He was shocked how p how his old friends from the bureau treated him. So did he have any problems like that?

    Eddy Inserra: In fact, he had a big problem like that as soon as he wouldn’t give up, his informant’s name. That became a problem actually. The the FBI called him in one of the documents that I have.

    It’s a memo that he wrote right after he came back from the FBI interrogating him. So he was told to report to the FBI in Boston by himself. And this was from his IRS superiors that say that, they want you over there, you gotta go talk to them. And so he went over there. And there was two agents in the room with Fred and they interrogated him asking if he had taken bribes at all.

    Yeah. And Fred used he, he outwitted them saying, I can’t say anything. This is an on ongoing investigation. If he, if you want me to say anything about this, you’re gonna have to get my [00:24:00] superiors to sign off on this. And, whatever the process was. And he felt like it was unbelievable because he said, who’s accusing me of this?

    They wouldn’t tell him. But eventually he figured out that it was this textile manufacturer that I mentioned earlier, Bernard Goldfine, his sort of right hand woman, her name was Mildred Paperman. She had she’d already been convicted and so was Bernard Goldfine, but they had said that Fred was taking bribes from them.

    So they’re taking this information from convicted, felons. And she said she had proof of it. So she had a check made up to the initials, FGP and who else, that’s Fred’s initials. Yeah. Fred G passed story. So Fred started laughing when they pulled that out. He said, do you guys have any idea who this is?

    It’s not me. And it was for Maine Senator Frederick g Payne, with the same initials. And that was easily documented in his paperwork that he was accepting bribes from gold mines. It’s really interesting how he outsmarted them [00:25:00] and I guess they didn’t do their homework good enough, but, they went after him hard and even after he left the IR Rs they tried to, I think one of, one of the documents says you didn’t report $2 of your tax income or something like that. Just busted his dogs. Oh my

    Gary Jenkins: God. I’m in a heap of trouble then.

    Eddy Inserra: Yeah. But the thing that he did have.

    And I, I can’t say it for sure, but he did have, in his back pocket, was a list of police and politicians that did take bribes. And that’s what up in, in that newspaper behind me, he was supposed to release this list. There was the media believed that he was gonna release these names during his press conference.

    He didn’t, and I believe that was an insurance policy that he kept in his pocket to keep them away. That’s my belief. I can’t confirm that, but that’s my sort of theory on that. Yeah.

    Gary Jenkins: Yeah. I tell you what in Boston, greater Boston, that area, having a list of policemen and politicians that have been taking bribes, that’s like shooting fish in a barrel.

    Just take out about 10 out and name the rest.

    Eddy Inserra: I tell you what, [00:26:00] I do have that list. It was in the bar.

    Gary Jenkins: Oh, do you? Oh really? Yeah.

    Eddy Inserra: Yeah. Is

    Gary Jenkins: that gonna be on your website? Is that gonna be on your website or are you just keeping that to yourself?

    Eddy Inserra: I thought long and hard about that, and I don’t think it’s fair to ruin or tarnish any family or anything like that.

    So I, that’s not gonna come out.

    Gary Jenkins: Yeah. Interesting.

    Eddy Inserra: That has nothing to do with me. That’s not my,

    Gary Jenkins: I, I’d have to agree with that, that those were different times, different days. Yeah. And there’s no use hurting in what would be innocent people today with that kind of information, especially Boston seemed like it’s a.

    A small community in, in, in a way, it’s not like New York where you’re spread out over all these boroughs and Los Angeles, where you’re spread out over, 25% of the state. It’s more like Kansas City, more like a small area that is Boston. And so a lot of people, everybody knows each other in some manner.

    Eddy Inserra: Yeah exactly. Couple of degrees of separation if that.

    Gary Jenkins: Yeah.

    Eddy Inserra: Yeah.

    Gary Jenkins: Interesting.

    Eddy Inserra: Yeah.

    Gary Jenkins: All right, Eddie and [00:27:00] Sarah, confidence of the mob, the IRS agent who took down the mafia and then advised them. So a really interesting book. Guys. I’ll have links to the website or to the Amazon page where you can buy this book.

    I’d highly recommend you buy it and when you do, go in there see, I don’t know, it’s about a quarter of the way in and find that find that QR code and. Go to that website and listen to some, I listened to a couple of three of those interviews. Really interesting stuff. That off the stuff that you can’t get everything in, but it’s interesting.

    I understand about that.

    Eddy Inserra: Thanks Gary. Yeah. That’s a upcoming podcast. We’re gonna have all full interviews and all that stuff with all. Oh,

    Gary Jenkins: Are you gonna do one yourself or with somebody there in Boston?

    Eddy Inserra: We’ve, it’s not gonna be a live podcast. It’s actually a bunch of clips thrown together.

    So it’s, oh,

    Gary Jenkins: I see.

    Eddy Inserra: Okay. Yeah we put it all together. It’s taken a couple years, so far, 12 episodes. We’ve got IRS agents in there, mafia members. We’ve got Fred’s ex clients and family. It’s really interesting. So you can check [00:28:00] that out on the website.

    Gary Jenkins: Yeah. When is that coming?

    Eddy Inserra: So we’re shooting to start releasing the end of May. So last week in May. Okay.

    Gary Jenkins: I love board. I always need another podcast to listen to myself.

    Eddy Inserra: Yeah. Yeah. Only gonna be one season. It’s not gonna be a multiple season thing.

    Gary Jenkins: That, that was my next question. It was gonna be a limit limited edition, if you will.

    Limited season. You’re not gonna keep going year in and year out like I do.

    Eddy Inserra: Yeah, no, there’s not enough content, but we’ll do behind the scenes and we’ll do some live stuff in Boston and things like that. Yeah. Okay. If anybody knew Fred or of him, please contact me too on the website. Okay. Love to hear about.

    Gary Jenkins: All right. Great. Alright Eddie and Sarah, I really appreciate you coming on the show.

    Eddy Inserra: Thanks, Gary. Great to meet you.
  • Gangland Wire

    Inside the Winter Hill Gang: The Untold Story of Joe Mac

    04.05.2026
    In this episode, host Gary Jenkins, a retired Kansas City Police Intelligence Unit detective, sits down with author and mob expert Springs Toledo and discusses the Boston Winter Hill Gang and its notorious members. Springs’ book, “Don’t Talk About Joe Mac: The Life, Wars, and Secret History of the Man Behind the Winter Hill Gang”

    Springs Toledo provides an exhaustive look at Joe McDonald aka Mac, a pivotal yet often overlooked figure in the Boston criminal landscape, especially during the 1960s-1990s. Springs, a Boston native, brings a unique perspective and personal anecdotes that enrich our understanding of the intersections of crime, family, and community within the city.

    They explore Joe Mac’s early life and how his background shaped his role in organized crime. Springs shares how Mac was an elder statesman in the underworld, feared and respected for his ability to organize the rackets in Somerville and maintain a significant network of relationships across various neighborhoods.

    Joe Mac’s methods of operation were emblematic of a time when the Irish underworld was gaining ground in a city dominated by Italian crime families. Springs discusses the stark differences in these organizations, from their cultural practices to their hierarchies.

    Springs also highlights the complexities of Joe Mac’s personal life, discussing his relationships with his family, especially his daughter Jacqueline. Their conversations reveal a side of Mac rarely seen in crime stories — a devoted father struggling with his dual identity as a loving parent and a cold-blooded criminal. Throughout the episode, Springs captures the essence of Mac’s character, noting that while he was involved in heinous acts, he also exhibited genuine love for his family, a contradiction that adds depth to his narrative.

    As the conversation unfolds, we examine the dynamics within the Winter Hill Gang, particularly the relationships among Joe Mac, prominent figures like Whitey Bulger, and Howie Carr. Springs shares fascinating insights into Mac’s cautious nature and strategic approach to power. He articulates how Mac operated in the shadows, steering clear of public scrutiny while effectively managing the group’s criminal enterprises. The episode paints a vivid portrait of a gang operating amid violence, betrayal, and survival.

    In addition to discussing the various criminal exploits, Springs shares some gripping anecdotes that illustrate the real-life implications of this lifestyle. His stories about Joe’s attempts to balance family life while dodging law enforcement showcase the constant threat that loomed over their lives, encapsulating the dangerous allure and traumatizing consequences of organized crime.

    We also touch upon the significant events that defined the gang wars in Boston, including Joe Mac’s suspected involvement in notorious hits and how the landscape of crime shifted in response to law enforcement’s increased focus on organized crime. Springs dives into the enigmatic character of Joe Mac, unraveling his military background, his unyielding commitment to the underworld, and how he managed to stay a step ahead of rivals and authorities alike.

    In closing, Springs reflects on the motivations behind his book—his desire to portray the human side of a man branded a monster while exploring the broader themes of morality, family, and the haunting legacy of crime. As we wrap up, it becomes clear that “Don’t Talk About Joe Mac” is not just a biography of an infamous crime figure, but a complex narrative that invites readers to ponder the true cost of a life steeped in organized crime.

    This episode is a riveting exploration of character, culture, and crime, offering audiences an engaging glimpse into the storied history of Boston organized crime, the Winter Hill gang through the lens of one of its most pivotal figures, Joe Mac.

    Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire

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    Springs Toledo JOe mac

    Gary Jenkins: [00:00:00] hey, all your wire tappers out there. Gary Jenkins back here in the studio of Gangland Wire. I’m a retired Kansas City Police Intelligence unit detective, doing a podcast mainly about organized crime.

    We might stray into drugs every once in a while, but primarily about Italian based organized crime or, and then sometimes we get into Irish based organized crime. I’ve done a story on the Westie in the past and a few other stories like that. So today we’re gonna talk about the.

    Crossing of the Irish and and the Italians in Boston area, which is a really well known, famous story. A lot of great characters. And I have with me a man who wrote a book about this. Springs Toledo, welcome Springs.

    Springs Toledo: Thank you very much, Gary. Happy to be here.

    Gary Jenkins: Great. Now guys, the books is, don’t Talk about Joe Mack the Life Wars and Secret History of the Man Behind The Winter Hill Gang.

    And I’ve always wondered about this Winter Hill gang. I’ve always heard of it and Whitey Bulger came out of that and was so famous, but I’ve never really. [00:01:00] Seen anything or know anything about the background of it. And Springs, Toledo has somebody, a guy called Joe Mack that was involved in that and he’s really gone into it in depth.

    Springs, tell us a little bit about yourself, how you got into this.

    Springs Toledo: I’m a native of Boston, which did help, the accent helped open doors.

    Gary Jenkins: We can tell.

    Springs Toledo: But I don’t even try to hide it anymore. And I have a background in, in boxing, which also helps, that’s a breeding ground for, leg breakers and enforcers.

    Historically, in Boston, a lot of ex fighters became gangsters or, involved in that life. I went to Northeastern got a graduate degree in criminology. And I I didn’t, I never became a police officer. I worked with, actually with juvenile delinquents and troubled youth for many years.

    I’ve written several books some about boxing, some about an historical figure named John Brown, who’s an abolitionist, so I’m running the gamut. But Joe McDonald was a name that I heard whispered for many years, growing up. He had a very long criminal career over five decades.[00:02:00]

    And, so he was considered something very serious. But what I began to notice as the book started coming out after John Madano became a cooperating witness, as he’d say. Is that not much was known about this individual. What I knew is that he was about 20 years older than everybody else. So he’s an elder statesman in that world.

    So I started poking around. I know some guys who were involved in that life. I know some other guys who were very connected to very serious individuals who were active in the Boston Underworld during these years, the sixties, seventies, eighties, into the nineties. Yeah. So I started, asking around and the things I started to hear were very downright alarming about who this man was and that he was the guy not Whitey Bulger.

    There was what they’ll all tell you the deeper you get into the operators in that world is that Whitey Bulger is. Largely a mythology. And that in Somerville especially, he wasn’t really that respected. Joe Mack, however, was Joe Mack was, he [00:03:00] was the go-to guy. And upon doing all kinds of research, field research, but also I’m trying to corroborate everything.

    People are saying you can’t just take what people have to say at face value, especially if they’re, underworld figures. Yeah. A lot of ’em have a self-interest as so what I would do, I had a little strategy. What I would do is I would talk to one guy in Southie if I heard a story that sounded intriguing or something about Joe Mack, what have you, and then I’d try to find another guy in Somerville or East Boston or Hy Park who didn’t necessarily know that individual. And if the stories match, I’d look into it further. For instance, I wanna make sure the guy wasn’t in prison at that time, that he’s allegedly known to have done something. So that’s how I began to put together a picture.

    And what the u unanimously what I found out is that Joe McDonald was really the, he’s the one that put together organized crime in Somerville, centered in Winter Hill. He organized the launch sh the rackets loan, sharking booking, sports betting, all of that. And he was a very feared individual.[00:04:00]

    He looked like a building superintendent. He was balding. He, no, he was nothing flashy about him. He was family man. But so I started digging deeper and I got his military records, and then the picture really started to come together because of what he went through during World War II in the South Pacific and the trauma that he suffered.

    I didn’t wanna write a straight True crime book. So I wanted to do something different. I didn’t want it to be ordinary. I wanted it to be get underneath the behavior. It’s the, the criminology major is, was showing it’s yeah. Was coming to the fore. So I wanna get underneath it.

    So I consider this book more of a nonfiction noir. ‘Cause if you watch those old movies, a lot of ’em have a theme where you have, the main character, the anti-hero. These are movies from the forties, all black and white. All shadowy. Yeah. They come back from World War ii and they’re troubled.

    They’re shell-shocked. JoEM, Joe Mack came back and he’s marred. Something about his personality had changed and he’s one of the few individuals that I’ve encountered who [00:05:00] actually age into crime. He didn’t age out of it like everybody else. He aged into it. But he was very good at what he did.

    He was a brilliant individual. Very strong-willed. Someone said that I talked to, they said that, all the fear, whatever fear he had was knocked out of him, in SVO sound. When his ship went down, which was a USS Quincy with his brother on it. So he became a, began to emerge as a fascinating figure.

    But what. Made me decide to write the book was when I was hooked up with his daughter by TJ English. I reached out to him and he, he told me about Jackie McDonald. I reached out to her and I said, I’m thinking about writing a book about your father, Joe McDonald. I don’t think that the the literature on him now really got him right.

    And she said, give me a night to drink about it. Yeah, so the next morning she told me she was she’ll tell me everything she knows and she was the right person because first of all, she was named for the brother that he lost in SVO sound that he never got over his little brother.

    Her name’s [00:06:00] Jacqueline. And like her father, she’s absolutely brilliant. She’s charismatic. She is incredibly honest. If she’s not sure about something she’d say. So nothing in it was, what she told me was about herself. It was nothing was ego driven. She wanted to tell the truth of her father.

    And what I began to realize early on is that you know this, you have victims of guys like Joe McDonald who killed dozens of people professionally, but he was a murderer. There’s no doubt about it. And you have a lot of victims, including in his own family. Not that he intended to hurt his daughters and his son, but his, who he was and what he was, did a lot of damage to his own family and she was the perfect person to talk to because she was so honest.

    She’s also very funny if, you read about her in the book, she comes across as a real character, very charismatic. So her story runs parallel with his, she comes out about the middle of the book. I trace her life alongside with his, and she had a memoir that she did many years ago and she shared that with me.

    [00:07:00] She’s she really is a force of good, if you will, in the book. She’s the one to cheer for, she’s the one to root for. Joe McDonald is a formidable figure, but he’s a dark and shadow. We figure. I do bring him out as much as I can and he is fascinating, but. I felt like I needed someone to root for the reader, yeah. And also, it’s women who love true crime the most. Yeah.

    Gary Jenkins: That’s so

    Springs Toledo: had to give nod to them, they’re gonna buy it.

    Gary Jenkins: That is true. And a story like this will will attract men and women both, sometimes those just straight, kill ’em all and let God sort ’em out. Of true crime books are not really attractive to women.

    That’s really interesting that. You’re showing the human side of this guy instead of just the crime side, which there every one of these guys that are professional criminals in this life have a human side. They, that’s what one thing that fascinated me about ’em, even way back when I started, went into the intelligence unit is these guys all had families and they had kids going to St.

    Pius up here and they played football and the families all showed up [00:08:00] when their kids played football and they were in little league and all that kind of normal stuff. On one hand, but yet they came over into the CI city in here. They came from the suburbs over in the city and were these gangsters all night long, and then went back home to their suburban homes.

    So that family side. That’s really interesting. I’m glad you did that.

    Springs Toledo: That’s compartmentalization. And Joe was the best at it. But there was something unusual about this case and that is that. Joe told nothing to anybody. His Winter Hill partners barely knew about his personal life. They didn’t know much about him.

    Yeah, nobody knew much about him. ’cause he didn’t confide in anybody. He did it the way you’re supposed to do it. As an organized, if you’re gonna get into organized crime, you want to follow his lead. And he lived a tough life. It’s nothing to get into in terms of choosing that as an occupation.

    However, he did confide in his daughters. He trusted them and he told them an awful lot, which he didn’t realize was traumatizing them. But. Jackie McDonald is blessed with a very good memory, so she was able to fill in [00:09:00] a lot of blanks about some of which were cold case murders and other just, real eyebrow raising incidents that happened.

    I think this book would’ve been invaluable to the FBI. Right up to the early nineties interest because of the stuff that came out, several cold case murders. I think I solved them. And, they were attributable, well attributed. I attribute them to Joe, a few. I know he did.

    But, people didn’t know, and he was a, excuse my saying, but he had. He was a real talent for that. He knew how to get you. He knew how to find you. He knew how to get you. And he also, like I said, he didn’t have any fear, so there was nothing holding him back. And that’s a difference from Whitey Bulger.

    What people don’t realize is that Whitey Bulger was a very careful man. And that’s why a lot of murders attributed to Whitey Bulger. He didn’t do, it doesn’t even, it, it offends his personality. He was the kind of guy, if he’s gonna kill you, you’re gonna be in the basement tied to a chair, or you’re gonna be a woman.

    He’s not on Northern Avenue in Boston in broad daylight, killing Brian Halleran. It’s not true.

    That’s not Whitey [00:10:00] bulge, that’s not how he operated. Joe Mack was a different beast altogether, and yet he was never indicted for murder. He was questioned maybe for one of them.

    And the title is really a reason for that because you didn’t talk about Joe Mack. That’s actually, that’s that’s. I like the title a lot. It took me a long time to get to that title. First title was Hey Joe, ’cause of the song. And I was like, ah. Nobody said, Hey, Joe to him. Where you going with that gun in your hand, huh?

    That’s right. You’re good. Yeah. Jimmy Hendrix. And then another title was the Wars of Joe Mack. That was a little too masculine that works, but it was too masculine. Yeah, don’t talk about Joe Mack really captures, what he was and how he operated.

    Gary Jenkins: Springs set the geographic scene.

    I’ve always been a little bit confused about this in Boston. IU Boston is unlike Kansas City, for example, what I’m familiar with. It has these really distinct areas in neighborhoods. Set the scene, the Italians African Americans, the Irish what set that up for us? [00:11:00]

    Springs Toledo: Okay, this is the, fifties, sixties, seventies that, that’s where most of the book is occurring.

    Especially 60, 70, actually into the eighties. Boston first of all it’s basically back then was an Irish Catholic city. Yeah. There were other ethnicities, but it was overrun with the Irish and there were neighborhoods. So you had. You had neighborhood crews, you had crews that were operated out of East Boston.

    That’s Barboza, south Boston was several of them. Jamaica Plain, the North End obviously was where the mafia was. Sented La Ostra. Somerville, Charlestown. And a lot of, most of these guys who were got into criminality. Not only did they have families, they also had occupations.

    They were long showmen, they were roofers. They had jobs. I’m a policeman. And back then policemen, you didn’t make a lot of money. So you were encouraged to supplement your income. Oh yeah. Some of these guys were, they were detectives by day and they’re doing heists at night and that was not uncommon.

    And. Over time, certain organizations [00:12:00] became more organized and the Irish, remember, were barely organized. They were more like, it was more like the old West when things got hot. It was also a whiskey driven, a lot of the heinous acts and the murders that started to happen with that, the Irish gang war in the sixties, everybody was drunk.

    Some of these guys were really nice guys and then they got to the whiskey and forget it. They become monsters. Not everybody, but but. Boston was also very segregated. Not like the south. It was, there was natural neighborhoods, I was in Hy Park, that’s where I came up. If I went to Southy, there was a problem ’cause I didn’t know a lot of people there.

    If somebody from Southie went to the North End, it’s a problem. You are Irish, you shouldn’t be here. You didn’t cross boundaries. Mattapan was Jewish and then it became black. Same thing. So everybody congregating together is very tribal in that sense. Less so now, but there are still pockets, what’s upsetting to me is that you barely hear the accent, and you’re walking through Boston, you don’t hear the accent too much anymore. You have to get to Dorchester. That’s their accent’s. 10 times worse than mine, [00:13:00] and mine’s pretty bad but Joe Mack was Joe Mack was born in Medford, Massachusetts.

    He then, he was in Somerville by about 1950. His mother had moved there as as clan, if you will. Had moved there, his sisters and brothers. And so he was in Somerville in Winter Hill, and that’s where he started to operate and that’s where he started to put things together.

    Gary Jenkins: Interesting. You say Winter Hill. So let’s talk about the beginnings or this Winter Hill gang. I’ve heard of this. Many times. And Whitey Bulger of course popularized it. So tell me about the Winter Hill gang and Howie Carr. And there’s a famous picture that see on internet or on Facebook with our Underboss Tuffy Luna and this guy that was the head of the Winter Hill gang and a couple other gangsters from New York.

    So tell us about the beginning of this Winter Hill gang.

    Springs Toledo: We deserves a lot of credit. He’s the one that really brought the stuff out beginning in the eighties. He had the guts to mention Joe Mack in print. That’s high risk. I’m not sure how much he did it, but he was really [00:14:00] attuned to it early.

    And he had some great books, but winter Hill’s a neighborhood in Somerville. It’s not South Boston. You talk to guys who were associated with the Winter Hill Gang, what they called the Hill. Really? It was called The Hill by those who were a part of that organization. They get very resentful about Whitey Belgium and some of them will say that Whitey Belger wasn’t Winter Hill.

    Whitey Belgium was a partner, but he was South Boston. Okay. Once, and it’s a big story, but once he, it’s all in the book. But once he betrayed his partners in 79. With Fleming and all the partners just about were either they were all indicted except for about this big horse racing scheme that was going on, across several states.

    But Whitey and Fleming were unindicted co-conspirators, and that was hint number one that prompted Joe to go to Howie Winter, who was the face of the organization and say, I’m gonna kill them both. He was talked out of it because it’d be too much heat because Whitey had some very serious connections.

    You can’t take that away from him. And so he was a high [00:15:00] risk hit. Joe would’ve done it anyway and would’ve probably made him disappear or threw it at another organization to get the heat off the hill. But he was restrained, which was, I thought was a big mistake, but who can tell then? But after he cleared the field of his rivals, who.

    Where his partners in the Winter Hill gang he ostensibly should have taken over the rackets in Somerville, but that wasn’t really the case. He had salty that was his turf. He was a local guy. Salty was really where he was. He was no longer really welcome is my understanding from guys who I talked to were there, he was basically chased out of the Marshall Motor’s garage in Somerville in Winter Hill, and that’s when he went to the Lancaster garage in, on North End, which is closer to home, closer to his.

    Space of operations. Yeah. But Whitey was very treacherous and he was Machiavellian in his methods. Joe at the time was already on the lamb because I don’t think Whitey would’ve survived that if Joe was close and saw what he was doing. So it’s a lot of what could have been, if Joe wasn’t in the wind because of several other crimes and murders he was [00:16:00] doing at the time, he was actually on the FBI’s 10 most wanted on 76, long before Whitey was on it.

    Gary Jenkins: Interesting. So then the relationship between Howie Carr and Joe Mack how was that, how did that shake down?

    Springs Toledo: Howie Winter, you mean,

    Gary Jenkins: or Howie Winter, I’m sorry.

    Springs Toledo: Yeah. Howie Winter was mentored by Joe Mack. See, Joe Mack was really, he was like the general, he was like the general on the field.

    The Irish don’t operate in a hierarchy. That’s an Italian thing. There’s no ring kissing in an Irish pub. It’s just a different culture. What they were partners. You had one guy up front. He was the face of it. That’s Howie. Howie was the face of it before Howie’s buddy McClain.

    In the early, in the early sixties. Joe though, the guy in the shadows, he used to say, I’m at the back of the bus. He’s at the back of the bus, but he’s the one with the map. He’s the go-to guy. The guy up front is the guy that gets hit. That’s the guy that gets indicted. So Joe was astute enough to, just stay in the [00:17:00] background, let the kids have it.

    But they were. Very close, very close. During the war they were, very tight-knit organization. These were friends. They were very affectionate with each other. They took care of one another. This is before Whitey came in. He was, he poisoned the well.

    But Joe and Howie and Buddy McClean and they, anos when they come in, they were very close. It was a kind of a band of brothers in a way. But Joe still made. Maintain that, everybody was at arms length with him. He was careful about everybody. There was a rift between Howie and Joe later in their respective lives in the in the eighties, into the nineties.

    I’m told that it was healed. I don’t think it was, and that’s unfortunate. But they were close to most of their lives, they literally went to war together on, on the street, you’re gonna form strong bonds when you know you’re looking at this guy and you gotta rely on him to watch your back.

    And

    Gary Jenkins: yeah,

    Springs Toledo: that’s what was happening.

    Gary Jenkins: So Irish, they didn’t kick up, if you will, to somebody above them. Everybody was a kind of a independent operator. If you got a piece of action and you had something going that you didn’t have to kick up to [00:18:00] somebody to be part of the Winter Hill gang, if you will.

    Springs Toledo: That was where the, there were a lot of crews around. They were called independents. And there’s a lot of them around in Boston in the sixties. But if you got too big and you started making real money, Patri was a power in Boston.

    Gary Jenkins: Yeah.

    Springs Toledo: Raymond Patri, he was a power in Boston. There’s no doubt about that.

    But there’s two schools of thought. Some believe that Winter Hill had to always kick up to them, kick to Providence. Others say? No, not really. Because first of all, he loved Buddy McClean. Buddy McClain was he was a very charismatic guy, very tough guy, and he was a man of his word, so they really liked him.

    So there’s the other school of thought is that, they liked Buddy, they gave him a pass on that. But every now and then they’d have to do him favors, maybe do some hits, things like that. Yeah. Yeah. But again, but in, in Boston it’s, like I said, it’s mostly Irish, it’s not set up like New York where the Italians are a real power that’s right there.

    He, one guy, matter of fact a name of one of the chapters in the book where I get into the Gangland war. Is Boston was [00:19:00] overrun with sick bastards, quote unquote, because there was just so many dangerous guys. There wasn’t a few here and there, like the gallows or it, there was hundreds of guys and there was damn near psychopathic they were called and underworld polls.

    There was savages, they go right to your house. And it was too many. This, one guy actually several believed that if there was a problem between Rhode Island. The Boston Underworld, meaning Boston Writ Lodge, including Somerville, Medford, Malden, all that. That.

    The Italians would’ve come to the table. ’cause the Irish underworld, the Boston Underworld here would’ve made it very much not worth it. Not worth the blood and the treasure. So it’s, yes, with very interesting culture here. What you couldn’t control the Boston underworld. They would just, Boston itself has a reputation.

    You don’t wanna invade this place.

    Gary Jenkins: Yeah, just ask the English, huh?

    Springs Toledo: Exactly. Yeah. We go way back with that stuff. Yeah.

    Gary Jenkins: Yeah it’s, I was at I went into the north end and looked around at Prince Street and all the place where [00:20:00] Jerry Angelo and all that was going on, and that is such a small.

    Discreet little area in that then, so you, they just operated and he was not any kind of a real power. It didn’t seem to be like, compared to patriarchal. He was under patriarchal of course. And he didn’t really, it’s like the Irish all had their own thing all around him. All, and he didn’t really have didn’t, I didn’t find any, anything I’ve ever seen where there was much to do between those two.

    Was there, did he have anything about that?

    Springs Toledo: He had he had two guys joe Russo, he was a killer. He was a very serious individual and a guy who has two names. Some call him Byi, some call him Zino. Larry was his name. Very serious guy. But that’s two guys. The other dangerous guys in the north end.

    They were getting up there in age. Meanwhile, like you just alluded to, this sur this surrounded, by these, these crazy guys. Yeah, but they, they did. There was some interplay, there was some contracts would be given to the Hill, for instance. That happened several times.

    The Hill would borrow [00:21:00] money from Angelou and Jou had a lot of money. They’d borrow money from him. Whitey Belger borrowed money from him with Fleming and actually didn’t pay it back. And then Joe Mack got out of the can. This is 80 late 86, 87, and him and Howie went to Fleming and Whitey and said, listen, you’re paying them back.

    Matter of fact, you’re paying them back a million because you made us look bad. We pay our debts, you pay him, you pay in back 1 million. And they did. They Whitey Bulger. Yeah. Whitey Bulger did not step two, Joe McDonald. In other words he wasn’t the power that Johnny Depp would have us believe.

    Gary Jenkins: Interesting. So let’s go back to the family just a little bit. His daughter Jack Le, so when he went to prison, did she talk about that? I have a friend who went to prison for several years and he talks, tells me a lot about his kids coming to visit him in prison. Did he talk about that? Did she talk about that?

    How that affected her?

    Springs Toledo: She she talks about her whole life and how he was a shadow in her life. She loved him, [00:22:00] but he brought a lot of chains behind him and a lot of ghosts and a lot of fear of FBI raids and things like that. Even when he was on the run from the FBI was on the, top 10 most wanted, it’s only six o’clock news all over the place in every post office.

    He would just show up and see her. He thought he was being a dutiful father. He’s showing up. He’s got these black sideburns, glued onto his face and she could see the ink dripping. He got his rug on his head he startled her a lot. So she. He was a cause of great anxiety.

    And then she became a mother, and then things started to change. She had to protect her boys. And while, he looked like he could be a good grandfather, he was an extremely dangerous man. And when he went away to prison, she tried to be a good daughter. She would send him clippings. Matter of fact, she sent him a clipping of I think it was a national examiner because her father was in it.

    It was about the top 10. FBI fugitives. And she pointed out she was into astronomy and she astrology and she pointed [00:23:00] out that Joe Mack and another guy named Leo Corey had the same birthday, July 14th. So she thought he’d get a kick outta that. He gets outta prison a few years later, and he shows up at her house with Leo Corey.

    Who’s still on the top 10 most wanted. And she, he opens the door. He said, do you remember this guy? And she turned, that, that was a scary, that was a very scary moment for her. Yeah. He’s bringing very, this is a convicted murderer. It’s a multiple murderer. She’s got bringing, he’s bringing it to her house like he’s an old friend.

    So that kind of stuff happened a lot. It almost show off like that. Look what I can do. Yeah. So she had, I, she did love him and she has since forgiven him. And I think this book is part of her process to forgive, what he put her through and what he put his other children through.

    Not intentionally, he tried to be a good father, but how can you. In that position.

    Gary Jenkins: Yeah. Yeah. When you bring that violence into the home, and you can’t help but bring that aura of [00:24:00] violence with you. When you live that life and when you come back into the home, there’s still that edge of violence that, that unspoken communication, you jump every time, somebody pulls up out in front and you’re running to the window to see who it is and there’s just always, always on edge.

    I, that would be it.

    Springs Toledo: Here’s a good story. So he’s on the run. This is in the I think it’s the late sixties. Joe’s on the run. She’s at home and Joe set his wife and kids up in Malden and a house on the hill. And originally he was gonna live there too. And it’s a, it is a great place. He’s up, he’s on a corner.

    He’s on a hill. You can see Boston from it. So it’s got a great vantage point for kind of a, a paranoid damaged war veteran. Yeah. So a call comes into the house. Voice says, you know who this is. She’s about 11, 12 years old. Voice says, you know who this is? Yes. Meet me at the bottom of the hill.

    So she gets her sister Patty and they meet their dad at the bottom of the hill. He takes them bowling and saga. He’s got the disguise on. Yeah. He’s got so many IDs, fake IDs, and he’s they [00:25:00] go to they, they go bowl and. You gotta wait for Lane. So he’s sitting there like this, he got his arms out.

    He’s feeling good about himself. He’s a good dad. He got his two teenage girls here and one of ’em, one of ’em, almost a teenager. And suddenly over the intercom, Thomas Campbell, your lane is ready. And he’s just sitting there. Thomas Campbell, he’s just sitting there. Finally his daughter says, pat says, dad, that’s you.

    Oh. And off he goes. So he wasn’t even sure who he was half the time. Yeah. So he’s my heart went out to him in that sense because here’s a man who made some very dark life choices and he’s trying to be a conventional father. Meanwhile, he’s gotta keep his eye on the clock, on the door, on the phone and everything else, all day long.

    Not to mention the fact that, there’s, it was dangerous lifestyle. But, his daughters, I, his daughters, they idolize him and they loved him. They didn’t fear him, he never raised his hand to them, never raised his hand to them, but they feared what he brought with ’em. Yeah. And that’s a theme book.

    Gary Jenkins: Yeah. Interesting. Yeah, that’s a, that’s that is so interesting. Think about this [00:26:00] era or of violent violence. I think somewhere in the book I noticed I was going through it where he may have been possibly one of the suspects on the Joe Barbosa head out in San Francisco when they finally got him and in.

    Springs Toledo: That’s fascinating because actually I had to take out ’cause of the publisher, I take about 15,000 words, but I really get into that. But that had to go. But what happened was. He had to go out there and kill a federal witness. And this guy was a civilian. This guy looked like a grandfather. And but he was gonna be a fence for some rear stamps that Joe had taken a million dollars worth of rear stamps.

    And this guy was gonna be the fence. He was a rear stamp collector out in Sierra Madre. Long story short, in January of 1976, Joe Mack drives out there, shoots him in the head five times in front of his wife, and then in February, that’s when Bob Bozer is killed February, 1976. This is January, 1976.

    Now, what I heard from two sources, and they’re pretty good, is that Joe did not go from Sierra Madre, [00:27:00] California back to Somerville. What he did was he went to Laurel Canyon and that’s where Alex Rocco was staying. Alex Rocco du played Mo Green in The Godfather. Oh,

    Gary Jenkins: yeah. Yeah.

    Springs Toledo: Yeah, he was a Winter Hill guy and Joe stayed with him on the lamb for so many weeks.

    I don’t know if it’s true. I couldn’t chase that down. No way you’re gonna find that out. But it was an intriguing little tidbit. So then in in February Bob Bozer is killed. Now when that news hit a bar in Boston called Clocks was a mob hangout. The bartender who knew all these guys.

    He got off the phone and he yelled out to the bar that Bleepity bleep stool pigeon. Animal Barbosa is dead and gone. God bless Joe Mack. That’s what he said. He just assumed Joe Mack did it. So what I’m trying to chase that down and what happens is so I’m talking to guys, who’re talking to guys. What I [00:28:00] found out is that one guy said no, this that, that wasn’t Joe that was kept in-house among the Italians because Bob Bza really took apart the Italians influences Yeah.

    In Boston. Yeah. He took them apart with lies. And however, there were three people in that van. I got these I got freedom of information documents and. What I was told by a made guy actually, is that it was Russo and Byi Zino. They’re the ones that took out Bob Bozo with a shotgun from a van.

    The van two seats were taken out of the van. The windows were painted black. This. Side windows were painted black and peeps were drilled into the side door and the back, so they worked hard to get ’em, but there was a third man in the van, so that’s a little intriguing. Could it have been Joe? I don’t know.

    Probably not. I’d have to say probably not, but nice story. And then from there, and then literally just a few weeks after that, Joe was in disguise. Remember now he’s already on the news as a as a top 10 fugitive. The FBI’s looking [00:29:00] for, and where is he? He’s in Walpole. How did I find out? I got everybody’s prison records.

    I could, and Brian Halleran, who turns up later in the book and then turns up dead later in the book. He’s in prison. Joe visits him. How do I know? It’s Joe’s Alias? John A. Kelly, that was his alias at the time. So he’s wanted by the FBI, he’s on the news and literally a week or two later. He’s visiting somebody in Walpole State Prison.

    From there, I trace him to Montreal. What’s he doing in Montreal? He’s sticking, he’s holding up a an ahed car robbery. With the Montreal Express, they had a great program, the Montreal Express. And Somerville, what they would do is they would just swap guys to do these big highs, get these ika, get these banks, and then just return.

    So it was awfully hard to catch ’em ’cause they’re just doing like a swap off. Yeah. Joe Mack. Was up there. And what he was doing was, and he, it was a white van, which raises an eyebrow, another white van. And the Amed car, the guy wouldn’t open the door. So they open up the [00:30:00] door of the back doors of the white van.

    And there is a World War II Browning anti-aircraft gun. And guess who’s behind it? Joe Mack. So this is a very busy man, and he should be, he’s retirement age but did he kill Boba? Probably not, but there was a third guy there. I would not be surprised. I know the Italians used him.

    Gary Jenkins: You brought something to Montreal Express Now what’s that?

    I, that I’m not from, I’ve not heard that term before.

    Springs Toledo: I wasn’t either, but that a lot of guys told me they

    Gary Jenkins: back heard your story there.

    Springs Toledo: Yeah, there is. Yeah. They were they were up, they were they were bank robbers. They went for the armor trucks. That was their forte. Very well organized.

    Very skilled. They were specialized and they would swap off with, winter Hills, sometimes with Southie and South Boston, I should say. South Boston and Somerville would, they were very close, they were very much aligned. They would swap off. I think one of ’em was the brother of a Bruins hockey player.

    Yeah.

    Gary Jenkins: Interesting. These guys, they got their connections. I found out more and more after I since I started doing this podcast, how many connections people [00:31:00] had between cities and even within a city connections to regular look like Square John, businessmen and just connections all over the place.

    It’s

    Springs Toledo: all over the place. Matter of fact, Joe was Joe was in contact with the guys who escaped from Alcatraz. I couldn’t prove it, but I heard that, he was sending them money and, and supporting them. I pro I didn’t find nearly 50% of what Joe was up to, but that’s more than anybody else.

    I think before this book, we knew about 2% of what he was up to. Yeah.

    Gary Jenkins: It was

    Springs Toledo: pretty guy. Sure. Yeah. He was a footnote in the most of the books. Just a footnote, if that. So

    Gary Jenkins: that’s the smart one, the one that keeps his head down and keeps out of the papers and everything. Did that, did you talk to John Ano?

    Springs Toledo: Yes. Yeah.

    Gary Jenkins: Interesting.

    Springs Toledo: I did. He was he loved, first thing he said was how much he loved him. All these guys, very serious guys. They’re very powerful guys in the underworld. And when I brought his name up the ones who were close to him, they would say I love that. I love that man. Loved him. They loved and [00:32:00] revered him.

    Other guys who were not as close to him, but who were very, operatives in the bus world. I bring his name up now, he’s been gone since 1997. And they’d look around like this. And they say, oh gee. So you know, his name is still enough to and matter of fact, I was told early on when I was poking around that I’m poking around in dangerous places and Joe still has friends and you don’t wanna cross these guys, so even now his his shadow still looms, if you will, but I think it approve of what I did because, what I heard is that he’s very honest. He would not want any biographer to pull a pull punches about who and what he was. I didn’t, yeah. But some of his friends warned me.

    They were, you gotta be careful with this, but I call it bachelor’s privilege. I’m not married, I have no kids. If I end up in a ditch, who cares? So I can take risks.

    Gary Jenkins: Yeah. That’s some truth. It’s just that last few minutes before you’d done the dish, you go, oh shit, I wish I was anywhere but here.

    I,

    Springs Toledo: I would ask to talk to a priest. Let me get a confession. That what you gotta do,

    Gary Jenkins: you

    Springs Toledo: know,

    Gary Jenkins: you’d be like I think it was Tony Citro. Supposedly the story was he [00:33:00] wanted to know if he could say a quick prayer before they did him in, but

    Springs Toledo: I hope they let him,

    Gary Jenkins: I don’t know.

    Steve Fleming, we met, you’d mentioned about Steve Fleming, the Rifleman, who was whitey’s buddy and you, I think you mentioned you had a story about Steve Fleming.

    Springs Toledo: Steve Fleming was it’s interesting he doesn’t appear too much in the book. One of the things I had to do with this, I had to do my best to keep the names down.

    One of the a fatal flaw in a whole lot of Boston and Underworld books than any underworld books is there was just 8,000 names. Too many names. There’s too many names. So I, so I mentioned him a few times ’cause you have to, but I’m not focused on Fleming, but I can tell you that Joe was very suspicious of Fleming as early as he was very suspicious of Whitey.

    He respected him. Fleming was a killer. More of an ambush killer than than a Savage or a guy who took a lot of risks. He was a lot like Whitey, like that. But no, Joe didn’t trust him because. He had a long bid and he got out early, and that’s always a cause for concern among those guys.

    Why are [00:34:00] you out early? They got a story and the stories backed up by the government. They were already in cahoots.

    Gary Jenkins: Yeah.

    Springs Toledo: But with the names, there was one guy, this is an example. He was actually an MDC cop who was part of the Winter Hill gang in the early sixties, and his name was Russ Nicholson.

    I don’t wanna keep saying Russ Nicholson, the cop. So I shortened it to Russ the cop. Yeah. And then as things went on and the, police department realized that this guy’s involved in the rackets, they forced him to resign. So then I started calling them Rust, the ex cop. Then Rusty ex-cop gets clipped probably by Georgie McLaughlin.

    He’s dead, so now he’s Rust the dead ex-cop. So I’m trying to be polite to the reader and keep the names down.

    Gary Jenkins: Interesting. That’s a good idea that I know about that, that people say I love what you did, but there’s too many names. I got confused who was who. So it’s

    Springs Toledo: yeah,

    Gary Jenkins: it’s always a problem with these deals.

    All right, Springs, Toledo. [00:35:00] Let’s see. All of a sudden I like there it is. There you go guys. And guys, I will have your his link to for all his books and the show notes and of course links to my books too, but links to all of these guy, these books. You had some even about John Brown.

    You wanna go back into little Civil War history? Why check those out too. Guys, thanks so much for coming on the show.

    Springs Toledo: My pleasure.
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Über Gangland Wire
Gangland Wire Crime Stories is a unique true crime podcast. The host, Gary Jenkins, is a former Kansas City Police Intelligence Unit Detective. Gary uses his experience to give insigtful twists on famous organized characters across the United States. He tells crime stories from his own career and invites former FBI agents, police officers and criminals to educate and entertain listeners.
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