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. Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to "buy me a cup of coffee" To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent 'Brothers against Brothers' or 'Gangland Wire,' the documentaries click here. To purchase one of my books, click here. 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 ...