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When Fidel Castro came to power In Cuba in 1959, the American government wanted to see him gone, so they hatched plots and tried to assassinate him again and again and again and again. Needless to say, none of them worked, and some of the ideas were almost farcical. Learn more about the many failed assassination attempts on Fidel Castro on this episode of Everything Everywhere Daily. This episode is sponsored by Hexclad. Over a year ago I invested in a set of Hexclad cookware. I got a griddle, a stock pot and two frying pans and I have been loving it and I use it almost every single day in my house. Hexclad completely changed the game by combining the performance of stainless steel with the convenience of non stick in a single pan. Hexclad gives you a proper sear, great heat control and cleanup that doesn't turn into a whole second job after dinner. After I cook something, cleanup is a simple matter of wiping it off or just doing some very light scrubbing. 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I just got two Quint's T shirts myself and I love them as always. Everything at Quint's is priced 50 to 80% less than similar brands, and they can do that by working directly with ethical factories and cutting out the middleman. So you're paying for quality, not brand markup. Elevate your summer wardrobe. Go to quince.com daily for free shipping on your order and 365 day returns now available in Canada too. That's Q-U-I-N-E.com daily for free shipping and 365 day returns. Quince.com daily. After the 1959 revolution, Cuba moved from being a US aligned island to a radical nationalist and then openly communist state aligned with the Soviet Union. The Eisenhower and Kennedy administration saw the Cuban leader Fidel Castro as a direct threat to the United States and the Western Hemisphere, especially after nationalizations of U.S. owned property, the export of revolution to Latin America, the Bay of Pigs failure and the Cuban Missile Crisis. Removing Castro seemed to some officials like a shortcut to collapsing or weakening the regime. According to a report delivered in 2006 by Fabian Escalante, the former chief of Cuba's intelligence Service, there were 634 to 638 assassination attempts on Castro's life. However, he had a very broad definition of the word attempt. Escalante's work is usually described as counting plots, schemes, conspiracies and operational plans, not just physically executed assassination attempts. So if someone at the CIA came up with an idea, it was considered an attempt, even if no one ever acted on it. A more realistic number came from the U.S. senate's Church Committee, which investigated CIA abuses in the 1970s and found concrete evidence of of at least eight serious plots involving the CIA to assassinate Fidel Castro from 1960 to 1965. The first known CIA assassination plot against a Cuban revolutionary leader was actually aimed at Raul Castro, not Fidel. In July of 1960, CIA officials considered paying a Cuban pilot to arrange an accident on a flight carrying Raul from Prague to Havana. The plan was rescinded, but the message actually couldn't reach the pilot in time. But he later reported that he had no opportunity to carry it out anyway. Some of the best known plots came from the CIA's Technical Services Division associated with Sidney Gottlieb, the same official who was linked to Operation MK Ultra. The Church Committee later declassified many of these plots, some of which were, how shall we say, unique. For the purpose of this episode, I'm going to focus on some of the more out there attempts on Castro's life, since that's far more entertaining than your basic run of the mill assassinations. And there's also time constraints. Some of the most famous attempts to kill Fidel Castro centered around his love of cigars. The CIA was aware that Castro loved cigars, so they tried to take advantage of this on more than one occasion. The first of these was when they wanted to spike his cigars with a botulinum toxin. Botulinum toxin is a neurotoxic biological substance that, when not properly purified, is one of the most poisonous toxins known to man. The poison is a neuromuscular blocker, meaning it causes muscle paralysis in low doses and death in higher doses. The CIA arranged for poisoned cigars to be delivered to an unidentified person in Cuba in 1961. And after that, we don't know what happened to the cigars. But seeing as Fidel Castro did not die from poisonous cigars, we can assume that they were never given to him or were caught before he could take the lethal dose. Another assassination attempt involving a cigar was much more cartoonish. The CIA planned to rig one with explosives, hoping it would detonate when Castro lit it. It's unclear whether the CIA actually carried out the explosive cigar plan or if it remained just an idea. But it was of the most famous attempts against Castro and the one people know the most about moving beyond cigars. One of the more unusual ideas to end Castro's life involved a scuba diving wetsuit. While the plan was never executed, it was kind of interesting. The idea was simple. The CIA knew Castro had a hobby of scuba diving and exploring Cuba's coast. So they wanted to cover the inside of a wetsuit with a fungus that would give him a deadly skin disease. Other options related to scuba diving was to purchase a large number of Caribbean mullusks. The plan was to paint the shells of the mullus a bright color to draw Castro's attention to them. And once he was nearby, the shells, which were going to be laced with explosives, would go off, blowing up Fidel Castro. The plan was deemed impractical, but it did receive serious consideration. One plan that was implemented and was almost successful involved a poisoned milkshake. The CIA became aware that Castro visited the Havana Libre Cafe in Havana. CIA agents had recruited a counter revolutionary waiter to poison Castro's chocolate milkshake. They had ensured that a poisoned pill was hidden in the freezer of the cafe so that it could be dropped in Castro's shake without detection. When it was time to put the capsule into the shake, the pill was stuck in the ice tray. When the waiter tried to pull the poisoned capsule free, it broke and spilled all over the cafe floor. Castro received the unpoisoned milkshake that was prepared by the assassin and drank it without problem. The failure of this attempt became one of the most well known and documented assassination attempt failures. Beyond the technical tricks, the CIA also employed other more unsavory methods to try to take out Fidel Castro. They formed an unlikely alliance with the American mafia in the 1960s. Believing that their violent tactics would succeed where they had failed, the CIA approached organized crime figures including Johnny Roselli and Sam Giancana. The CIA offered both mobsters the equivalent of $1.2 million in today's money and and legal immunity if they took Castro out. The logic was ugly, but practical. Mafia figures had pre revolutionary casino and business ties in Havana. They hated Castro for shutting them down and had contacts who might be able to reach him. The mobsters came up with a few different plans, including slipping poison into Castro's drinks and a good old fashioned shooting. But none of these plans were ever implemented. The collaboration between the CIA and the mob was fairly short lived and unsuccessful. And after President Kennedy was elected, he moved away from the previous administration's extreme measures ending the alliance between them. Another attempt to kill Castro involved his lover, Marita Lorenz. The CIA recruited Lorenz in 1959 and gave her poisoned capsules to slip into Castro's drink which would kill him within 30 seconds. Lorenz later testified that she got cold feet and hid the capsules in a jar of cold cream, believing that they would be rendered useless. But Castro learned about the plot and confronted her. Strangely, he gave Lorenz a loaded gun and told her to kill him, which she clearly didn't do. When handing her the pistol, Lorenz reported that he told her, you can't kill me. Nobody can kill me, Lorenzo. And evidently he was right. Not every American plot aimed to kill Castro. The United States also attempted to assassinate his character. This is fundamentally different as they weren't trying to murder him, but instead trying to simply reduce his political power. One of the plans against Castro was a targeted attack against his beard. Castro's beard was a huge part of his public image. To destroy that image, the CIA planned to lace his shoes with thallium salts. Thallium salts are odorless, tasteless and highly toxic. They're considered to be slow acting poisons that target the nervous system. And one notable side effect is hair loss. By putting thallium salt into Castro's shoes, the CIA had hoped it would cause his beard to fall out, distorting his public image. The plan was put in place for when Castro was traveling outside of Cuba. They had expected Castro to leave his shoes outside his hotel room for polishing, which is how they would deliver the thallium salt. But the plan failed because Castro canceled his trip. Another plan to assassinate Castro's image was through the use of a chemical similar to lsd, which can cause hallucinations. Because Castro was a charismatic Public speaker. The hope was to undermine his image as a leader by spraying his broadcasting studio with the hallucinogenic chemical. The thought was, as Castro was speaking, he would hallucinate and come off as crazy and unreliable. This plan also failed because the chemical was too unreliable to be released in such a setting. Despite all of the attempts on Fidel Castro's life, he managed to survive all of them. Castro was once quoted as saying that if surviving assassination attempts were an Olympic event, I would win the gold medal. The attempts on Castro's life slowed down following an executive order given by Gerald Ford who declared that no employee of the US Government should engage, conspire or commit political assassinations. Ford's decree largely stemmed from the information released by the Church Committee while this order was in place. It was later revealed by the CIA that attempts on Castro's life continued up through the Clinton administration into the 1990s. The official assassination schemes made by the CAA were all classified under the codename Executive Action. According to the Cubans, under Dwight Eisenhower's Reign, there were 38 plots. JFK's administration had 42 assassination plots. President Lyndon Johnson's administration tried 72 times. Richard Nixon was the second most aggressive with 184. Jimmy Carter's administration had 64. Ronald Reagan was the most aggressive with 197. George H.W. bush had 16 tries, and Bill Clinton tapped out at 21 attempts. The plots all failed for multiple reasons. Castro had strong security, Cuban intelligence was rather effective. Many Cuban exile networks had been penetrated. Operational plans were often amateurish, and many proposals depended upon unreliable intermediaries. More fundamentally, the plots all assumed that killing Fidel Castro would solve the Cuba problem, and that was an incorrect assumption. By the early 1960s, the Cuban Revolution had institutions, a security apparatus, and more importantly, Soviet backing. Castro did matter, but he was not the only thing holding the regime together. If any one of the assassination plots had been successful, then Communist Cuba would probably have continued to function and the fundamental problem for the United States government wouldn't have changed. The man who ultimately assassinated Fidel Castro was Father Time. Castro had relinquished the presidency in 2008 after 49 years in power. He decided to step down because he was having health issues and at an age where he felt that he lacked the ability to govern effectively. After giving up power, Castro survived for another eight years to dying of natural causes in his sleep in 2016 at the age of 90. And I suppose if you live to be a nonagenarian and die of natural causes, you can claim to have won the assassination game. His younger brother Raul, who took over the leadership of Cuba, is still alive as of the recording of this podcast at the age of 96, the assassination plots against Fidel Castro remain one of the strangest chapters of the Cold War. They included serious covert operations, some reckless schemes, exile conspiracies, organized crime, contacts, and ideas so bizarre that they almost sound like satire. Yet beneath the exploding cigar stories was something very real the Cold War fears that a small island nation aligned with the Soviet Union and sitting just 90 miles off the coast of Florida could permanently alter the balance of power in the Americas. The efforts to kill Fidel Castro failed, but they revealed how far governments were willing to go in the name of national security during the Cold War. The executive producer of Everything Everywhere Daily is Charles Daniel. The associate producers are Austin Otkin and Cameron Kieffer. Research and writing for the episode is provided by the Olivia Ashe I want to remind everyone that we're getting into the home stretch for the sixth anniversary episode, which will be appearing on July 1st. I'm going to be turning the show over to all of you. You can record a brief audio message that will appear on the show@speakpipe.com everything everywhere. Tell me who you are, where you're from, and what your favorite episode is. There's a link to the site at the top of the show notes and on the website. Today's review comes from listener Lily and the Smith family on Apple Podcasts in New Zealand. They write incredible podcast. I listen every day while working and play it on road trips for my family to listen to as well. We've just joined the Completionist Club too. Thank you, Gary. Well, thanks Lily. I'm glad to see the Kiwi Completionist Club is expanding. Maybe you could put together a trivia team and call them the All Brains. Remember, if you leave a review of the podcast on any of the major podcast apps, you too can have it right on the show.
Host: Gary Arndt
Date: June 23, 2026
In this episode, Gary Arndt explores the astonishing and often bizarre history of assassination attempts against Fidel Castro, the longtime leader of Cuba. Drawing from declassified files, historical reports, and colorful anecdotes, Gary discusses both the serious and the outlandishly farcical plots devised—mostly by the CIA—to remove Castro from power. The episode focuses on how these plots, ranging from poison cigars to exploding seashells, reveal the Cold War paranoia of the era and the extremes to which governments would go.