Monkey Morales: The CIA, Castro, the Mob and the JFK Connection
In this explosive episode of Gangland Wire, retired Kansas City Intelligence Unit detective Gary Jenkins dives deep into one of the most complex and mysterious figures of the Cold War era—Ricardo “Monkey” Morales, a Cuban exile whose life intersected with the CIA, the anti-Castro underground, Las Vegas mobsters, and even the JFK assassination.
Gary welcomes Rick Morales Jr., son of Monkey Morales, and author Sean Oliver, co-writer of the new book Monkey Morales: The True Story of a Mythic Cuban Exile Assassin, CIA Operative, FBI Informant, Smuggler, and Dad. Together, they unravel the incredible life of a man who was at once a patriot, a spy, and a killer.
Rick recounts growing up in Miami’s Little Havana, where his father’s shadow loomed large—rumored to have ties to the JFK assassination and known for his secret missions across the world. From escaping Cuba as a disillusioned Castro loyalist to training as part of the CIA’s Operation 40 assassination unit, Monkey Morales lived a life that reads like a spy thriller.
Sean Oliver walks listeners through Monkey’s covert missions in Africa’s Congo, his deep ties to other operatives like Frank Sturgis and Barry Seal, and the secret wars that connected Cuban exiles, the CIA, and organized crime. The conversation also explores how Monkey became entangled with Lefty Rosenthal, the Chicago Outfit’s Las Vegas gambling mastermind, and how his bomb-making skills were used in mob turf wars across Florida.
The discussion culminates with Morales Jr.’s chilling memory of his father confessing he was in Dallas on the day President Kennedy was shot—and that he had seen Lee Harvey Oswald in a CIA training camp. Whether you believe Morales was a hero, a villain, or both, his story weaves through some of the darkest and most intriguing chapters of 20th-century American history.
📘 Get the book: Monkey Morales: The True Story of a Mythic Cuban Exile Assassin, CIA Operative, FBI Informant, Smuggler, and Dad
🎙️ Highlights include:
• How Monkey Morales went from a Cuban intelligence officer to a CIA-trained operative
• The secretive Operation 40 and its links to the Bay of Pigs, the Congo, Watergate, and Dallas
• Morales’s work for the FBI and the CIA—and his dangerous double life in Miami
• His connection to mob figure Frank “Lefty” Rosenthal and the Outfit’s Florida operations
• A firsthand account from Morales Jr. about his father’s claim to have seen Oswald in CIA training
• The moral code of Miami’s Cuban bombers—and how it vanished when Colombian cartels arrived
Listen now on Apple Podcasts, Spotify, YouTube, or your favorite podcast app.
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Transcript
Speaker: [00:00:00] All right, well, hey, all you wire tappers out there. It's good to be back here in the studio of Gangland Wire. Uh. Gary Jenkins, retired Kansas City Police Intelligence unit detective turned podcaster now, and I have another story and we're gonna talk a little bit about the JFK murder and a connection to it, and a little bit about Lefty Rosenthal.
Speaker: And you guys know that I know a lot about ref lefty Rosenthal because he was calling back to Kansas City every once in a while to our mob guys and, and so, so I'm really anxious to talk about this story, but first, let me introduce my guest today and I'm really excited to have these guys on here.
Speaker: I have Rick Morales, Rick Morales, Jr, actually, and Sean Oliver. Welcome guys. Well, thanks Gary. Love the show. So, uh, you know, I, I looked at the two chapters you sent me and, and learned about the book and, and a little bit about your lives and especially yours, Rick, and it's, it's just fascinating as hell.
Speaker: Rick and I were talking a little bit before you [00:01:00] came on here. We, I didn't tape it or anything, Sean, and about I had, you know, I was a policeman and I had kids growing up and, and Rick, his dad wasn't a policeman, but his dad was, was in that. Kind of a violent, kind of a uh, occupation, if you will, about bringing that edge of violence home to your family.
Speaker: And there's no way to, you don't, you know, you know, let it loose on them, but you've been in some violent circumstance. All day long, or Rick's case, maybe his dad's case, maybe for the last several weeks. And then he comes home and, and so it's, it's just an interesting, uh, family dynamic I always think. But, let's start with you, Sean.
Speaker: Tell us a little bit about where you came from. I know you're an author and you've been into wrestling.
Speaker 2: Yeah. Um, I'm from a planet called New Jersey. No, no. Strange. I think you've covered a lot of my residents in the past. I, neighbor, just a couple of weeks ago ago, I heard you doing Bobby Manna, who was very much a, a local of mine.
Speaker 2: Yeah. And my neighbor, Chuck Webner, who you may or may not know, not a mobster, [00:02:00] but I was a, I was a film and television actor for a long time. I, um, I directed television commercials. I, I was in entertainment and then I fell into covering professional wrestling. I wasn't a wrestler myself. I know the physique has you fooled.
Speaker 2: Yeah, so I had a pro wrestling production company, and then through that, kind of fell into that world. And so my first few books when I started writing were covering that world. And then, um, wrote some novels and then, uh, my first foray into true Crime, certainly not reading it, but writing it came when I met a man.
Speaker 2: Beside me known as, uh, Rick Morales Jr. When I found out who his father was. And I went on a hunt for someone alive who could talk to me about Ricardo Monkey Morales. And that's how I met Rick, I guess six years ago now, Rick. Yeah.
Speaker 3: Six years.
Speaker 2: Yeah. And we began [00:03:00] developing the story initially for television, um, as it's, uh, really lends itself to an episodic.
Speaker 2: It's, yeah, it's so vast to the story, but COVID hit production shut down. We, it was impossible for anyone to produce anything of this scope. So about two years ago, I said to Rick, we had been past our last. Pass was, uh, Rob Reiner, I guess. And I said, Rick, I, let's do this as a book. You know, I have an inn in the publishing world.
Speaker 2: I have, you know, multiple books out. Let's tell your dad, we gotta get the story out. So that's when we started doing this for publication.
Speaker: Interesting, interesting. And it is interesting story. We go from, uh, JFK assassination to Las Vegas, like I said, and, and a whole bunch of stuff down in South America. Rick, you gotta tell us about yourself.
Speaker: You know, Richard Morales. Yeah, Ricardo Mon Monkey Jr. I guess her dad was called Monkey Morales. So tell us a little bit about [00:04:00] your childhood. It had to be a little bit different than a lot of other childhood.
Speaker 3: Yeah,
Speaker: yeah. A little
Speaker 3: bit different than Sean's, I would say. Yeah. I was, uh, born in Miami. I got older brother, younger brother, and a sister.
Speaker 3: I was born in 63 in Miami the same year. JFK gets second vaccinated. So I was there, but I wasn't able to. To watch my dad do much 'cause I was only a couple of months old. So grew up in Miami. My dad and my mom left Cuba. My dad was a G two government agent for the Castro government when it took over.
Speaker 3: And then during the two years between 58, 59 or 59 and 60. Disillusioned as much as many were. He was trying to figure out which way the direction of the country was going, and eventually they, uh, tried to kill him. They, they put him on a hit list because his father was a judge for Batista's regime and [00:05:00] had, his father was a judge in the Batista regime, so they were eliminating anybody that had to do anything with the Batist regime.
Speaker 3: So eventually he escapes through the Brazilian embassy. He spends like 82 days there with a bunch of other people. And, uh, eventually they're taken out and he moves to Miami where he immediately goes to work for Cuban revolutionary groups. Because he's, he is got the abilities. He's a bomb maker. He is a master bomb maker.
Speaker 3: He is a sniper, so he's been trained in the government and all those things. So he joins Cuban power groups in Miami trying to fight. Against the castor regime and, and the power. And that's where he starts making his name for himself and then that leads to further jobs with government agencies. CIA what All this time we're kids.
Speaker 3: We're not aware in the early ages, like when I'm young, I'm not aware of what my father is [00:06:00] doing, but eventually there comes times when I see news stories on tv, they try to hide it from us, but they can't. We hear stories from friends. I would go to friend's house when I was young and they would one day be my friend, and then the next day they weren't allowed.
Speaker 3: And when I would ask them at school, what happened is, your dad's Monkey Morales, he was involved in the JF Kennedy assassination. That's what everybody in Little Havana was saying. And so they weren't allowed to come to my house anymore for fear of anything happening at my house that they would become, uh.
Speaker 3: Involved and heard or something. So I grew up with that stigma, you know, uh, as a child. Wow.
Speaker: Crazy. Well, like, do you guys, uh, Sean, did you did you get into investigating any of these pro anti-Castro groups down in Southern Miami? They were, it was Southern Florida. They were all kinds of little groups down there.
Speaker 2: Yeah, so you've got Cuban exiles coming here [00:07:00] landing in the waiting arms of the CIA who are able to train arm,
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