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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 about the many failed assassination attempts on Fidel Castro on this episode of Everything Everywhere Daily.
After the 1959 revolution, Cuba moved from being a US-aligned island to a radical nationalist and then an openly communist state aligned with the Soviet Union.
The Eisenhower and Kennedy administrations 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 then 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 Fabián 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 “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 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 Raúl Castro, not Fidel. In July 1960, CIA officials considered paying a Cuban pilot to arrange an “accident” on a flight carrying Raúl from Prague to Havana. The plan was rescinded, but the message could not reach the pilot in time; he later reported that he had no opportunity to carry it out anyway.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 linked to MKULTRA.
The Church Committee later declassified many of these plots, some of which were….how shall we say, unique.
For this episode, I’m 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 are time constraints.
Some of the most famous attempts to kill Castro centered around his love for cigars.
The CIA was aware that Castro had a love of 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 1961. After that, we do not know what happened to the cigars, but seeing as Castro did not die from poison, we can assume they were never given to him or were caught before he could take the lethal dose.
Another assassination attempt involving a cigar was even more cartoonish. The CIA planned to rig one with explosives, hoping it would detonate when Castro lit it. It is unclear whether the CIA actually carried out the explosive cigar plan or if it remained just an idea, but it remains one of the most famous attempts against Castro.
Moving beyond cigars, one of the more unusual ideas to end Castro’s life involved a scuba diving wet suit. While the plan was never executed, it is very interesting.
The idea was simple: the CIA knew Castro had a hobby of scuba diving and exploring Cuba’s coast, so they covered the inside of a wetsuit in a fungus that would give him a deadly skin disease.
The other option, related to scuba diving, was to purchase a large number of Caribbean mollusks. The plan was to paint the shells of the mollusks bright colors to draw Castro’s attention to them. Once he was nearby, the shells, which were going to be laced with explosives, would go off, blowing up Castro.
The plan was deemed impractical but received 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 Café 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 shaker, the pill was stuck in the ice tray.
When the waiter tried to pull the poisoned capsule free, it broke open and spilled all over the cafe floor. Castro received the unpoisoned milkshake that was prepared by the assassin and drank it. The failure of this attempt became one of the most well-known and documented assassination attempts.
Beyond technical tricks, the CIA also employed other, more unsavory methods to try to take out Castro. They formed an unlikely alliance with the American mafia in the 1960s, believing their violent tactics would succeed where others had failed.
The CIA approached organized crime figures, including Johnny Roselli and Sam Giancana. The CIA offered both mobsters $1.2 million in today’s money and legal immunity if they took out Castro.
The logic was ugly but practical: Mafia figures had pre-revolutionary casino and business ties in Havana, 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 good old fashioned shootings, but none of the plans were implemented.
The collaboration between the CIA and the mob was fairly short-lived and unsuccessful. After Kennedy was elected, he moved away from the previous administration’s extremist 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 they would be rendered useless.
Castro learned about the plan and confronted her. Strangely, he gave Lorenz a gun and told her to kill him, which she clearly didn’t do. When handing her the pistol, Lorenz reports that he told her, “You can’t kill me. Nobody can kill me,” 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 kill Castro, but instead trying to kill his 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 are considered to be slow-acting poisons that target the nervous system. One notable side effect is hair loss.
By putting Thallium salt in 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 Cuba. They had expected Castro to leave his shoes outside his hotel room for polishing, which is how they would deliver the Thallium salt.
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 charismatic leader by spraying his broadcasting studio with the hallucinogenic chemical. The thought was that 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 the attempts on 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 made, it was later revealed by the CIA that attempts on Castro’s life continued up through Bill Clinton’s administration into the 1990s.
The official assassination schemes made by the CIA were classified under the code name Executive Action.
According to the Cubans, under Dwight D Eisenhower’s reign, there were 38 plots. JFK’s administration plotted 42 assassinations. President Lyndon Johnson’s administration tried 72 times. Richard Nixon was the second-most aggressive, with 184. Jimmy Carter’s administration tried 64 times. Ronald Reagan was the most aggressive planner in 197. George HW Bush tried 16 times, and Bill Clinton tapped in at 21 attempts.
The plots failed for several reasons. Castro had strong security, Cuban intelligence was effective, many Cuban exile networks had been penetrated, operational plans were often amateurish, and many proposals depended on unreliable intermediaries.
More fundamentally, the plots assumed that killing Castro would solve the “Cuba problem.” That was a weak assumption. By the early 1960s, the Cuban Revolution had institutions, a security apparatus, and Soviet backing. Castro mattered enormously, but he was not the only thing holding the regime together.
If any one of the assassination plots had been successful, then Communist Cuba probably would have continued to function, and the fundamental problem for the US government wouldn’t have changed.
The man who ultimately assassinated Fidel Castro was Father Time. Castro had relinquished his presidency in 2008 after 49 years in power. He had decided to step down because he was having health issues and at an age where he felt he lacked the ability to govern effectively.
After giving up his power, Castro survived for another 8 years, dying of natural causes in his sleep in 2016 at the age of 90. 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 Raoul, who took over the leadership of Cuba, is still alive at the age of 96.
The assassination plots against Fidel Castro remain one of the strangest and darkest chapters of the Cold War. They included serious covert operations, reckless schemes, exile conspiracies, organized-crime contacts, and ideas so bizarre they 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 from Florida, could permanently alter the balance of power in the Americas.
The efforts to kill 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 Oetken and Cameron Kieffer.
Research and writing for this episode were provided by THE Olivia Ashe.
I want to remind everyone that we are getting into the home stretch for the 6th anniversary episode of the podcast on July 1.
I’m going to turn the show over to all of you. You can record a brief audio message at www.speakpipe.com/EverythingEverywhere and tell me who you are, where you are from, and what your favorite episode is.
There is a link to the site at the top of the show notes.
Today’s review comes from listener Lilly and the Smith Family on Apple Podcasts in New Zealand.
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 completion club too! Thank
you, Gary.
Thanks, Lilly! I’m glad to see the Kiwi Completionist Club expanding! Maybe you could put together a trivia team called the All Brains.
Remember, if you leave a review of the podcast on any of the major podcast apps, you can have it read on the show.
