After Fidel Castro ousted business-friendly military dictator Fulgencio Batista in 1958 and instituted a series of communist reforms in Cuba, he quickly made an enemy of the neighboring United States. Intent on bringing the revolutionary down, the US government spent the next several decades engaged in fruitless attempts to weaken, sabotage, and even assassinate Castro, who remained in power until 2006. These assassination schemes ranged from run-of-the-mill hitmen to convoluted conspiracies worthy of Wile E. Coyote.   The Olympics of Assassination Attempts Fidel Castro shows off a newspaper headline about a plot to assassinate him, New York, 1959. Source: The Guardian   Executive Order 11905, signed by Gerald Ford in February 1976, formally banned US government agencies from assassinating foreign leaders. It states: “No employee of the United States government shall engage in, or conspire in, political assassination.” That political assassinations were technically legal before that may come as a surprise. The number of documented attempted political assassinations since then, including Muammar Gaddafi, Slobodan Milošević, and Saddam Hussein, suggests it hasn’t been particularly well-enforced—especially when it comes to the US’s premiere spy outfit, the Central Intelligence Agency.   The CIA is not known for its candor, so the most targeted individual in the organization’s history may never be known—but Fidel Castro, famed leader of the Cuban revolution or reviled communist dictator, depending on the audience, must occupy a top spot.   Arguably the greatest spy agency in the world acknowledged at least eight attempts to assassinate Castro during the Eisenhower, Kennedy, and Johnson administrations in testimony to the US Senate—while the leader’s own spy chief, Fabian Escalante, claims the number was over 600, up to and including the Clinton administration. The true number of plots is no doubt somewhere in between. Castro himself once said, “If surviving assassination attempts were an Olympic event, I would win the gold medal.”   These bungled assassination attempts stand out for several reasons. First, of course, the sheer number, particularly those Castro’s spy chief claims were plotted long after the practice was “outlawed.” Second, the CIA’s impressive inability to actually kill Castro, who made it to age 90 and died of natural causes. And, perhaps most importantly, how truly absurd—even downright laughable—some of the assassination plots were, drawing a sharp contrast to the agency’s powerful and professional reputation. Here are the five most ridiculous ways the CIA conspired and failed to off Castro during the Cold War.   1. Lactose Intolerance Caricature of Castro by Edmund S. Valtman, 1960. Source: Library of Congress   Castro had a well-known and slightly bizarre obsession with dairy and reportedly ate ice cream multiple times a day—so why not use it against him? Both sides have reported the details of this plot, and some of the finer points are disputed, but the basic outline remains the same. In 1961, or possibly 1963, the CIA churned up a scheme to poison one of Castro’s frozen desserts—whether an ice cream cone or a milkshake is a matter of contention—and got as far as transferring the poison, via the mafia, to a would-be assassin in the employ of a café in Havana that Castro frequented.   When the big moment arrived, however, physics reportedly intervened. The poison—possibly a vial or a pill, the details are murky—had been stashed in the freezer and, perhaps predictably, became frozen stuck. In trying to dislodge it, the employee broke and spilled it, rendering it useless. That Escalante believes this was the closest the CIA ever got to actually taking out Castro is perhaps the most laughable part of all.   2. Smoke Him Out Castro lighting a cigar, accompanied by Che Guevara. Source: The Independent   For all its intelligence, the CIA evidently could not learn much about Castro beyond what the general public already knew. Most of their plots, rather than using any secretive knowledge they had about the dictator, seemed instead to revolve around Castro’s most well-known habits—including his love of cigars. Two different cigar-related plots were reportedly dreamed up in apparent denial of the fact that someone as famous and controversial as Castro would surely have a variety of precautions in place to prevent his precious Cohibas from being tampered with.   The plot for which there is actual evidence involved a scheme to taint the dictator’s cigars with poison. In 1960, an official from the CIA’s Office of Medical Services was provided with a box of Castro’s favorite cigars and told to lace them with enough botulinum toxin that just putting one in his mouth would be fatal. Records show that the treated cigars were delivered to someone in 1961, but the trail stops there. No one knows what happened to them or whether they ever made it anywhere near the Cuban leader.   A less believable (if possible) but better-known plot involving exploding cigars has also been said to exist. In 1967, the Saturday Evening Post reported that during Castro’s United Nations visit the previous year, a CIA agent had approached the New York Police Department, providing security for the event, with a plan to slip Castro an exploding cigar. No other evidence for this fiery plot exists, and researchers have since suggested it was simply “tabloid fodder” or even a false flag designed to distract the press from the CIA’s true (yet equally absurd) plans.   3. Under the Sea Photo of James Donovan, a lawyer the CIA tried to involve in one of their assassination schemes, with John F. Kennedy, 1962. Source: John F. Kennedy Presidential Library and Museum   When he wasn’t busy turning Cuba from a military dictatorship into a communist dictatorship, Castro enjoyed relaxing under the sea, taking in the beauty of Cuba’s ocean water from a diving suit. The CIA was having none of that and devised several plans to assassinate the leader as he tried to wind down beneath the waves.   A more well-known plot involved selecting a particularly noteworthy seashell, rigging it with explosives, and planting it where Castro was sure to stumble upon it during one of his dives. Once he picked it up—kaboom! More than just a vague notion, officials actually bought (and presumably read) two books on Caribbean mollusks for further research. The plan was discarded as impractical when the CIA determined there was no shell, both large enough to contain the necessary volume of explosives and spectacular enough to guarantee Castro’s attention.   Not willing to abandon the surefire “scuba-related accident” theme, a less well-known CIA brainstorming session resulted in an even more puzzling game plan: gifting the dictator a diving suit dripping with disease. The CIA’s zany schemes division treated a breathing apparatus with tuberculosis and then dusted an accompanying suit with a fungus that causes mycetoma, a serious infection that can lead to amputations if left untreated.   How, exactly, the suit could have been safely transported without infecting anyone in its vicinity was apparently not important enough to come up in any testimony, but it was all for naught. The individual the CIA had determined would deliver the suit, James Donovan, a lawyer involved in negotiations to free Bay of Pigs prisoners, was tipped off that there may be an attempt to tamper with a suit he had already purchased. Donovan did ultimately gift Castro a non-lethal dive suit—and secure the release of over 1,000 prisoners.   4. Crowdsourcing Castro speaking during a visit to the United States, April 1959. Warren Leffler. Source: Library of Congress   The CIA wasn’t above outsourcing the unpleasant task of taking out the Cuban dictator—their earliest schemes famously involved paying off members of the mafia (angered by Castro having shut down their Cuban casinos) to do the deed. Efforts to work with the disgruntled Cuban diaspora who had set up camp in Florida after the revolution were also documented.   Perhaps frustrated by their seemingly inexhaustible collection of foiled plots, senior officials in the Kennedy administration floated the idea of offering cash rewards to Cubans for killing members of Castro’s regime and communist party operatives, as well as the big man himself. Operation Bounty proposed rewards of up to $1,000,000 for such targeted attacks, which would be advertised via leaflets dropped over the country. To collect, all they had to do was present proof of death, the deceased’s party membership card, and, of course, the leaflet. Who these items would have been presented to and how seems like a reasonable question.   So, how much would you rake in if you took down Castro himself? A measly $0.02. According to Senate testimony from Edward Landsdale, who held a number of roles with the Department of Defense during the Kennedy Administration, the puny reward was proposed as a way “to denigrate … Castro in the eyes of the Cuban population.” Unsure that the scheme would actually work, the plan also included dispatching agents to kidnap some of the lower-level targets themselves to convince the locals their neighbors were cooperating in secret while sowing distrust within the nation’s communist party. Like many of the CIA’s half-baked ideas, the operation was never launched.   5. Jesus Saves Members of the Church Committee meeting with President Gerald Ford’s legal counsels, 1975. Source: The Intercept   Save the best for last—if “best” means “most absurd.” This last plot is so outlandish that, if it weren’t for the transcript of actual Senate testimony from a CIA agent attesting to its existence, it likely would have gone down in history as an urban legend. And while there’s no evidence that any attempt was ever made to carry out the preposterous plan, the details in that testimony suggest it was more than just a fleeting thought.   The brilliant idea: convince the very Catholic Cuban populace that Castro was the Antichrist and then fake the second coming of Jesus to prompt Cubans to rise up and overthrow (and, presumably, kill—it’s the Antichrist, after all) him.   Yes, really.   According to CIA agent Thomas A Parrot’s testimony to the Church Committee, it was Lansdale (again) who concocted this particular scheme. Agents would be enlisted to spread the word around Cuba about Castro being the Antichrist “and then on whatever date it was, that there would be a manifestation of this thing. And at that time—this is absolutely true—and at that time there would be an American submarine which would surface just over the horizon off of Cuba and send up some starshells. And this would be the manifestation of the Second Coming and Castro would be overthrown…”   Details about how, exactly, agents thought they would manage to persuade Cubans that Castro was the Antichrist or how rockets would convince them of Jesus’s imminent return are disappointingly absent from the testimony. Lansdale himself, unsurprisingly, denied any such plot ever existed.   Fidel Castro arrives at what is now Reagan National Airport, Washington DC, 1959. Source: PBS   It’s worth noting that when not cobbling together outlandish schemes to assassinate their Cuban nemesis, the CIA was also busy plotting hare-brained antics designed to undermine and humiliate him, hoping to goad the Cuban public into overthrowing him—including slipping him LSD before a televised speech and lacing his boots with poison designed to make his signature beard fall out—which also produced a zero percent success rate. If nothing else, these abject failures are perhaps something to keep in mind the next time someone alleges the existence of a widespread government conspiracy.

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