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The story of the CIA’s many failed Fidel Castro assassination attempts

In many ways, the late Cuban leader Fidel Castro was a man of myth and mystery. For years, rumours have swirled about him; everything from the speculation that he slept with 35,000 women during his lifetime to his trying out for the New York Yankees baseball team before his entry into politics. But whilst separating fact from fiction can be challenging, one story stands out more than most – namely that there were more than 600 Fidel Castro assassination attempts, many of them orchestrated by the CIA.

Ranging from the slightly creepy to the downright absurd, including a plot to plant a beautifully painted shell packed with explosives to tempt the diving enthusiast president, the slapstick gadgets of early James Bond films have nothing on the the CIA’s assassination attempts.

Fidel Castro during an address in Cuba.

Credit: Getty

 

Castro governed as Cuba’s Prime Minister from 1959 to 1976 then as president from 1976 to 2008, having seized power in 1959 at the climax of the Cuban revolution. During this time, communist rebels led by Castro and Che Guevara rose up against the right-wing president Fulgencio Batista. In the early 1960s, with the Cold War looking increasingly warm, the presence of a communist ally of the Soviet Union only 100 miles from the US coast was considered a genuine threat to both US security and the impenetrability of the US’s ideological sphere of influence. Much to the ire of successive US presidents, Castro’s famously charismatic leadership style meant that at the time he was portrayed as a Robin Hood figure and enjoyed widespread popularity on the island. With the US desperate for regime change, this mix of factors was to prove fatal – or at least, it was supposed to.

Contrary to the United Nations Charter, which prohibits states to overthrow or change the political system of another state or its government, attempts to kill Castro started almost immediately after the Cuban revolution. Somewhat ironically, they became more intense and organised during the administration of John F Kennedy, who would of course be assassinated himself. Between 1960 to 2000 every US administration made some attempt on Castro’s life, peaking between 1969 to 1974, during the Nixon administration. Castro additionally became a target for Cuban exile groups, with many of their attempts also being backed by the CIA.
Among the earliest attempts, and like in all good spy movies, there was a plan involving a beautiful femme fatale. Marita Lorenz, a German-born American and a lover of Castro’s in the late 1950s was recruited by the CIA to kill him in a Havana hotel room. Described by a retired FBI agent Frank Lundquist as a young woman who was visibly “in over her head” in her relationship with a man of such power, Lorenz had recently undergone an abortion ostensibly of Castro’s child, the circumstances around which are still disputed. Citing “handling personal matters” as her reason to see Castro, she set out on her mission using two capsules filled with poison provided by the CIA. However, all did not go to plan, as Lorenz explained in an interview with Vanity Fair: “I knew the minute I saw the outline of Havana I couldn’t do it.” Castro, having already twigged what was about to happen, also had other ideas: “He laid down on the bed and 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.”
Fidel Castro smokes a cigar

Credit: Getty

By Castro’s own admission, the closest the US ever came to successfully assassinating him was with a chocolate milkshake poisoned with botulinum toxins, prepared by a trusted hotel worker who had secretly been working for the CIA. Arguably the most famous however, was in the form of the exploding Havana cigar, which was intended to be offered to the leader when he visited the United Nations in New York. The plot, which was revealed by a policeman in 1967, prompted Castro to pose gloatingly with a newspaper carrying the story whilst smoking a cigar. Not one to be deterred, he continued to smoke until 1985 when he decided cigars were bad for his health and quit.

In their determination to do away with the Cuban statesman, America even took to outsourcing their dirty work to a very surprising group of hitmen. Whilst the American mafia may be commonly thought of as fundamentally at odds with a crime fighting institution such as the CIA, the release of a 702 page dossier known as The Family Jewels, compiled by the agency in 1973, revealed their collusion with the crime syndicate in multiple Fidel Castro assassination attempts. According to the document, which detailed illegal and inappropriate actions undertaken by the CIA, selected agents were, in 1960, asked to make contact with high-ranking “gangster elements” with the access to dispose of Castro, covering their tracks with the stories of unpaid gambling debts. After multiple aborted attempts, the partnership was cancelled in the aftermath of the failure of the Bay of Pigs incident in 1961.

Fidel Castro’s grave in Santiago de Cuba Fidel Castro’s grave in Santiago de Cuba.

Credit: Getty

Aside from their many murderous attempts, the CIA also embarked upon a series of “character assassination” missions designed to discredit and embarrass their arch enemy. These included using poison to destroy his signature beard – he had once reportedly said that he would shave it off only when economic sanctions had been lifted – and spiking him with LSD ahead of a public speech to make him lose control.

Having retired from public office in 2008 and all but disappeared from public life in later years, rumours of his death consistently swirled for some time before his actual death. Surely knowing the end was near, in August 2016 to mark his 90th birthday he released a column in Granma, a state run newspaper, mocking the US’s attempts on his life over the years: “I almost laughed at the Machiavellian plans of US presidents.” He passed away just three months later, on 26 November 2016, and whilst his real cause of death was never revealed by the Cuban government, it was no doubt less somewhat less exciting than the wild plans of CIA agents, with not an exploding cigar in sight.

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