Former dictator and revolutionary Fidel Castro was easily one of the most prominent and polarizing figures of the 20th century. Not only was he responsible for the Cuban revolution, but he also transformed the island nation into a communist and autocratic state.

In turn, this put him at odds with much of the world—and the United States in particular. While he eventually died of natural causes in November 2016, he survived—reportedly—over 600 assassination attempts during his lengthy political career.

Not every assassination plot is created equal, however. Here are 10 of the most insane attempts to take down Fidel Castro…

1. The infamous exploding cigar: Yes, the rumors that the CIA once planned to plant a cigar packed with explosives, which would ignite when he lit the stogie, are true. It was reported by the Saturday Evening Post in 1967 that government agents had approached an NYPD officer in 1960 and asked him to carry out the assassination.


2. The contaminated diving suit: American lawyer James Donovan was once propositioned by the CIA to contaminate one of Castro’s diving suits. This would be done using a toxic strain of fungus, which would’ve given the communist leader a fatal skin disease.


3. The femme fatale: The CIA tasked Marita Lorenz, a former lover of Castro’s, to seduce and assassinate him. Her mission was to slip two botulism-toxin pills into one of his drinks. Later, she admitted that she was far too nervous to carry out the attempt. “I knew the minute I saw the outline of Havana I couldn’t do it,” she said in an interview.


4. Poisoning his pen: This James Bond-esque attempt to kill Castro involved turning an ordinary pen into a dart gun. This gun would be filled with a toxic hypodermic needle and used to jab the revolutionary by someone in his own entourage.


5. Lacing his cigar with drugs: Easily one of the more peculiar attempts on Castro occurred in 1960, when the CIA had the idea to lace one of his cigars with LSD so that he would become high while giving a speech. The goal was actually to assassinate his character. This way, the citizens of Cuba would stop trusting what he said to them.


6. The explosive seashell: The CIA once tried to utilize Castro’s affinity for scuba diving against him. The plan was to plant explosive devices in beautifully colored and strange-looking conch shells at all of his favorite diving spots. The idea was that he would pick them up, and they would detonate right then and there.


7. The botulin cigar: Clearly, the CIA knew Castro loved to smoke a Cuban cigar. That’s why they planned to lace another with a lethal dose of botulin. The hope was that Fidel would light the cigar and inhale the smoke, which would then rapidly kill him.


8. The disappearing beard: Not to be outdone by the insane LSD fiasco, a 1975 Senate Intelligence Committee report stated that the CIA planned to destroy the leader’s character by lacing his clothes and shoes with thallium salt. The salt, they hoped, would eventually lead to his iconic beard hair falling out, which they thought would greatly embarrass him.

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9. The contaminated tissues: Once upon a time, the CIA planned to get ahold of Castro’s handkerchiefs and contaminate them with toxic diseases. This way, when he went to blow his nose, he would contract the disease and eventually die.


10. The poison milkshake: It’s rumored that the CIA’s attempt to poison one of Castro’s milkshakes in 1963 was the closest they ever came to successfully assassinating him. It was only thwarted after the pill containing the poison became stuck to the bottom of the freezer where it was stored. The waiter serving the dictator ripped it open—and spilled the contents—while trying to unstick it.


The CIA certainly had some silly ideas on how to assassinate the communist dictator. They do not, however, get points for creativity.

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