The CIA’s Wild Chase: The 600+ Attempts to Take Down Castro

 

Explosive Seashells and Poison Cigars: The CIA's Bizarre Plots Against Castro

When it comes to covert operations, the CIA has always been known for its ingenuity, persistence, and, sometimes, wild imagination. Nowhere is this more evident than in the agency's relentless attempts to take out Cuba's Fidel Castro. Picture this: a revolutionary leader who survived over 600 assassination attempts, dodging everything from poison cigars to explosive seashells. Sounds like something straight out of a spy thriller, right? Well, that’s because it nearly is.

     The CIA’s obsession with Castro began when he took the reins of Cuba as its Prime Minister. Back then, the CIA, led by the notorious Allen Dulles, wasn’t just planning; they were plotting. And who better to help take out the cigar-chomping revolutionary than some of America’s most dangerous mobsters? Enter Sam Giancana and John Roselli of the Chicago Outfit—two mafia bigwigs who had their own beef with Castro after he shut down their lucrative Havana casinos.

     So, the CIA struck a deal with the devil, using a middleman named Robert Maheu, an attorney with a flair for the dramatic, to bring the mobsters into the fold. The idea was simple: Castro had to go, and they were willing to try anything—poison pills, deadly cigars, even a femme fatale armed with a kiss of death. The plots were as audacious as they were doomed to fail.

     Take, for example, the cigar caper. It was straight out of a James Bond film. The plan was to inject Castro’s favorite cigars with a botulinum toxin so potent that just one puff would be his last. But like many other plots, this one never made it past the drawing board.

     Then there was the time they toyed with the idea of an explosive seashell, meant to detonate while Castro indulged in one of his beloved scuba diving sessions. It was the perfect plan—until someone realized that finding the right shell might be a bit tricky.

     And while the CIA was busy hatching all these fantastical plots, they were also battling Castro's network of double agents and loyalists, who were just as determined to keep their leader alive. Many of the operatives trained by the CIA were caught and, in some cases, met a gruesome end at the hands of a Cuban firing squad. Castro’s knack for survival turned him into something of a legend, even as the U.S. government’s reputation took a hit.

     Check out "1963 Spy Swap With Castro," where on April 21, 1963, three gaunt and battered Americans walked out of Cuba’s notorious La Cabana prison and flew to freedom. After enduring 949 days of brutal captivity, they were finally released in a tense prisoner exchange. These men weren’t just any prisoners—they were undercover CIA officers, caught red-handed in a bugging operation that nearly cost them their lives. Their daring return was a pivotal moment in Cold War history, shining a light on the high-stakes espionage games played between the U.S. and Cuba.

     This brings me to a scene in my spy thriller, Mission of Vengeance. In the novel, CIA spymaster Corey Pearson and his elite team notice an unsettling surge in Russian military activity in Cuba—a legacy of Castro’s era. They spot the Russian spy ship Yantar cruising down the U.S. East Coast before docking ominously in Havana.

     But when the ship suddenly hightails it out of there, headed straight for the Dominican Republic, Pearson knows something big is going down. The Yantar isn’t just playing tourist; it’s about to smuggle Russian spies and Hezbollah terrorists out of the Caribbean, and it’s up to Pearson to stop them.

     Back in the real world, despite the best efforts of the CIA, the Mafia, and a host of other conspirators, Castro lived to a ripe old age, passing away at 90 from natural causes. The man who survived hundreds of assassination attempts was ultimately defeated by time itself. And while the CIA’s attempts to kill Castro may have all the trappings of an action-packed thriller, they also serve as a reminder that even the most well-laid plans can go awry when you’re up against a man with as many lives as a cat.

     So next time you light up a cigar or take a dip in the ocean, remember Fidel Castro—an adversary so formidable that even the CIA couldn’t bring him down, no matter how many times they tried. And if you’re curious about how modern-day espionage might look, check out Mission of Vengeance. It’s got all the intrigue of the Cold War with a fresh, contemporary twist.

Robert Morton is a member of the Association of Former Intelligence Officers (AFIO) and authors the ‘Corey Pearson- CIA Spymaster’ series. Check out his latest spy thriller, ‘Mission of Vengeance