CIA tried to kill Castro with an exploding cigar!

The 5 Craziest Fidel Castro Assassination Plots From the CIA

The CIA and creativity go hand-in-hand. Take, for instance, its creation of wild programs like MK-Ultra. Which, among other things, studied LSD’s potential as a mind-control drug, for use on our soldiers. This creativity is apparent in the multitude of assassination attempts and plots the CIA developed for Cuba’s longtime communist dictator, Fidel Castro.

Fidel Castro Assassination Plots

The following are the five most “outside-the-box” Fidel Castro assassination plots confirmed by the Church Committee, a U.S. Senate task force aimed at investigating security agency abuses of power. In all likelihood, many more became developed and likely attempted. Fabian Escalante, Castro’s former head of intelligence, claimed the dictator survived 638 assassination attempts. Castro himself proclaimed, “If surviving assassination attempts were an Olympic event, I would win the gold medal.”

Poison/Exploding Cigar

Castro was an avid cigar smoker. During the early 1960s, the CIA reportedly researched cigars with explosive charges rolled in with the tobacco. One New York City police chief claimed the CIA approached him with a plan to get Castro to smoke an exploding cigar during his visit to the United Nations in 1966. Sources claim the CIA also toyed with the idea of slipping a neurotoxin-coated cigar in with Castro’s supply. Supposedly, the CIA never tried to execute either plan, and claim they were simply misdirection to cover other assassination efforts.  

The Mafia

In 1960, under President John F. Kennedy, the CIA contracted with Mafia members on the FBI’s 10 Most Wanted Fugitives list to kill Fidel Castro. This isn’t the only example of the CIA operating in accordance with the old “The enemy of my enemy is my friend” principle, but it is especially ironic considering that Bobby Kennedy headed a historic crackdown on organized crime as part of his brother’s staff. According to CIA documents released in 2007, the agency contacted Sam Giancana, a successor of Al Capone in Chicago, and Santo Trafficante Jr., a powerful mob boss in Miami, to discuss the removal of the Cuban dictator.

The Mafia had extensive business dealings in casinos, hotels and resorts in Cuba that curtailed when Castro’s revolution nationalized all private business. The CIA hoped they would jump at a chance to open Cuba back up by removing Castro.

At a meeting set up by Las Vegas mobster “Johnny” Roselli in New York City, Giancana agreed to have Juan Orta, one of his men in the Cuban government, slip Castro a poison pill. The CIA manufactured a deadly cyanide pill and delivered it to Orta. The story goes that Orta fumbled the pill when trying to slip it into Castro’s drink. When he attempted to remove it, the capsule broke and the poison lost. Orta demanded to be released from the mission shortly thereafter for fear of being discovered. The CIA and the mob then began preparations for another attempt, using Cuban doctor Anthony Verona. Details about the plan are sparse, and the mission halted in preparation for the Bay of Pigs invasion.


Another plot involved Castro’s German-born, American-citizen lover, Marita Lorenz. She met Castro on her father’s ship in Havana’s harbor when she was 19 years old. Castro boarded the boat with a group of uniformed soldiers, and the two were apparently taken with each other at first glance. Not long after, once Lorenz returned to the U.S., Castro sent a private plane for her. The plane took her back to Cuba where she stayed with Castro in his personal suite. 

Marita seen here with Fidel Castro.

Eventually, she became impregnated by Castro. He then drugged her, kidnapped her, and her pregnancy was aborted before she was sent back to the States. Once there, a CIA agent approached her and offered her the opportunity to get revenge on Castro by slipping poison pills into his drink. She returned to Cuba and reunited with Castro, but she lost her nerve and told him everything. Once she did so, he reportedly handed her his pistol and dared her to shoot him, knowing she wouldn’t. He turned out to be right. Lorenz reports that instead she gave up the gun and they made love, later returning to the U.S. 

Diving Suit/Conch Shell

Along with cigar smoking and women, Castro also loved diving. So, naturally, the CIA made plans to target him during his daily swims. According to CIA documents, plans existed to paint a large conch shell a brilliant, eye-catching color in the hope that Castro would see it and swim closer to investigate. Of course, explosives filled the conch. Another plan reportedly involved planting tuberculosis bacteria in Castro’s diving suit. It became abandoned since getting Castro to pick up a specific diving suit would have been a longshot, at best. 

Poison-Pen Syringe

In remarkably ironic fashion, on the very day President Kennedy was assassinated, the CIA gave a Cuban “asset” in Paris a pen containing a syringe loaded with a deadly poison. CIA reports indicate that on Nov. 22, 1963, the meeting with Castro’s potential assassin was underway at the exact moment of Kennedy’s shooting. It is unclear why the asset, was never able to administer the poison. 

CIA tried many times to assassinate Fidel Castro.

Despite all the attempts on his life, Castro lived a long life and died of natural causes at age 90 in 2016. The Cuban communist regime remains intact. Fidel’s brother, Raúl Castro, is currently head of the regime. Plots on Castro deserving of honorable mention include a plan to gas his radio broadcast room with LSD. The use of thallium salts to destroy his trademark beard. Castro’s security team also discovered 200 pounds of explosives under a podium back in 2000.

Check out our podcast Skillset Live for even more crazy tales in history. Get in on the conversation on our social media pages or pick up a back issue at

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