An exploding seashell, a paramour, and tainted ice cream are among some of the more inventive tactics.

After years of avoiding assassination attempts by the US government, Fidel Castro died at age 90 on Friday, at the end of a decade of dealing with illness.

Castro’s longevity may even seem like the final act of defiance against the United States, which become his adversary since he first took power in Cuba in the late 1950s. The botched US-backed 1961 Bay of Pigs invasion meant to topple Castro could’ve ended in his death, but most other attempts involved more subterfuge and spycraft.

Fabian Escalante, a former head of the Cuban secret service who was charged with protecting Castro from would-be assassins, has claimed that Castro faced 634 attempts on his life, from the CIA, Cuban exiles, and others. Escalante’s count is quite possibly high (he counts 21 attempts under Bill Clinton, whose administration wouldn’t have had much motive after the end of the Cold War), but many American attempts have been verified by independent historians, government investigators, and journalists, especially as crucial documents have been declassified.

As the Church Committee, a Senate body which chronicled abuses by intelligence agencies in the mid-1970s, “The proposed assassination devices ran the gamut from high-powered rifles to poison pills, poison pens, deadly bacterial powders, and other devices which strain the imagination.”

1) The poisoned cigar

Probably the most famous attempt on Castro’s life, the cigar plot, originated in 1960, toward the end of the Eisenhower administration, according to the Church Committee.

“A notation in the records of the Operations Division, CIA’s Office of Medical Services, indicates that on August 16, 1960, an official was given a box of Castro’s favorite cigars with instructions to treat them with lethal poison,” the Committee’s report recounts. “The cigars were contaminated with a botulinum toxin so potent that a person would die after putting one in his mouth. The official reports that the cigars were ready on October 7, 1960; TSD [Technical Services Division, the CIA’s science/gadgets arm] notes indicate that they were delivered to an unidentified person on February 13, 1961. The record does not disclose whether an attempt was made to pass the cigars to Castro.”

There’s a popular belief that the CIA also tried to give Castro an exploding cigar, but this is much more poorly documented, and some historians believe it to merely be an urban legend.

2) The Mafia ice cream plot

In mid-March, 1961, Mafia contacts of the CIA came the closest of anyone to carrying out an assassination, according to Tim Weiner’s history of the CIA, Legacy of Ashes. “They gave poison pills and thousands of dollars to one of the CIA’s most prominent Cubans, Tony Varona,” Weiner writes. “Varona managed to hand off the vial of poison to a restaurant worker in Havana, who was to slip it into Castro’s ice cream cone. Cuban intelligence officers later found the vial in an icebox, frozen to the coils.” (Castro famously loved ice cream.)

There are some different versions of this story; Escalante recalls it happening in 1963, and with a chocolate milkshake instead of ice cream. One variant posits that the pills were not discovered by Cuban intelligence, but instead spilled out in freezer and rendered useless. But Escalante called the poison pill effort “the closest the CIA got to assassinating FIdel” in an interview with Reuters.

3-4) The exploding seashell plot and the poisonous diving suit plot

Scuba diving was one of Castro’s favorite hobbies, so perhaps unsurprisingly the CIA looked into the possibility of building an exploding seashell to kill him on one of his expeditions.

In 1963, the Church Committee report recounts, “Desmond Fitzgerald, chief of the [anti-Castro CIA] Task Force, asked his assistant to determine whether an exotic seashell, rigged to explode, could be deposited in an area where Castro commonly went skin diving.”

But that’s not the only diving-related plan the CIA had: “A second plan involved having James Donovan (who was negotiating with Castro for the release of prisoners taken during the Bay of Pigs operation) present Castro with a contaminated diving suit.”

Donovan is maybe most famous for negotiating the spy trade that returned American U-2 pilot Francis Gary Powers; he was portrayed by Tom Hanks in the 2015 Steven Spielberg/Coen Brothers movie Bridge of Spies. He was successful in securing the release of thousands of Cuban prisoners after the Bay of Pigs, but did not wind up murdering Fidel Castro.

The Technical Services Division of the CIA did wind up buying a diving suit, dusting its insides with a fungus that caused the chronic skin disease Madura foot, and put TB in the breathing apparatus. But the suit never left the laboratory.

5) The paramour

Marita Lorenz, Fidel Castro’s one-time lover, has said that she was recruited by CIA-funded anti-Castro groups in late 1959 and tasked with slipping him botulism-toxin pills. Her CIA contact, she claims, was E. Howard Hunt, a then-agent who would later go to jail for his role in the Watergate break-in.

As soon as her plane reached Havana, however, Lorenz was having doubts about killing Castro. Vanity Fair’s Ann Louise Bardach writes:

Even if she had had the will to go through with her mission, she had already botched it, having stashed the capsules in a jar of cold cream. When she looked for them, “they were all gunked up. I fished them out and flushed them down the bidet.” When Castro finally appeared, he was wary. “Why did you leave so suddenly?” was his first question, she says. “ ‘Are you running around with those counterrevolutionaries in Miami?’ I said yes. I tried to play it cool. The most nervous I have ever been was in that room, because I had agents on standby and I had to watch my timing. I had enough hours to stay with him, order a meal, kill him, and prevent him from making a speech that night, which was already pre-announced.

“He was very tired and wanted to sleep. . . . He was chewing a cigar, and he laid down on the bed and said, ‘Did you come here to kill me?’ Just like that. I was standing at the edge of the bed. I said, ‘Yes. I wanted to see you.’ And he said, ‘That’s good. That’s good.’ ”

Castro asked if she was working for the C.I.A. “I said, ‘Not really. I work for myself.’ Then he leaned over, pulled out his .45, and handed it to me. I flipped the chamber out and hit it back. He didn’t even flinch. And he said, ‘You can’t kill me. Nobody can kill me.’ And he kind of smiled and chewed on his cigar…. I felt deflated. He was so sure of me. He just grabbed me. We made love. I contemplated staying—to try talking to him later, after his speech, but it would be too late, because he rambles on for 8, 10, 12 hours. That was the hardest part. I wanted him to beg me to stay, but he got dressed and left. I just sat there by myself awhile. I left him a note. I told him that I would be back.”

Lorenz ‘s own testimony is less iron-clad than the internal CIA documents that the Church Committee had access to, so the details on this one are less certain, but given the CIA’s frequent poison-based attempts on Castro’s life, it’s not implausible.

6) The poison pen

In the early 1960s, the CIA made contact with a senior Cuban official known only as AM/LASH. “Each case officer testified that he did not ask AM/LASH to assassinate Castro,” the Church Committe report writes. “The record clearly reveals, however, that both officers were aware of his desire to take such action.”

AM/LASH asked for, and apparently received, a cache of high-powered rifles with scopes, which he intended to use for an assassination. But the CIA also offered him a ball-point pen rigged with a hypodermic needle “so fine that the victim would not notice its insertion.”

But AM/LASH apparently did not “think much of the device,” according to his CIA case officer, and complained the CIA could surely “come up with something more sophisticated than that.”

7) Character assassination through LSD-like drugs or debearding

These technically weren’t attempts to kill Castro so much as discredit him and undermine his rule. But they’re too strange to not include here.

“From March through August 1960, during the last year of the Eisenhower Administration, the CIA considered plans to undermine Castro’s charismatic appeal by sabotaging his speeches,” the Church Committee report writes. “According to the 1967 Report of the CIA’s Inspector General, an official in the Technical Services Division recalled discussing a scheme to spray Castro’s broadcasting studio with a chemical which produced effects similar to LSD, but the scheme was rejected by the chemical was unreliable.”

The TSD also experimented with dosing a box of cigars with a chemical producing temporary disorientation, which could lead to an embarrassing failed speech by Castro. The CIA inspector general also found a plan to dust Castro’s shoes with thallium salts, “a strong depilatory that would cause his beard to fall out.” It was supposed to be delivered to Castro when he was traveling abroad, and left his shoes outside his hotel room to be shined, but when Castro canceled the trip, the attempt was abandoned.

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