Myriad ways CIA tried and failed to assassinate Fidel Castro

1) Getting the Mafia to do it 

When a sizable cache of classified CIA documents, amicably called ‘Family Jewels,’ was finally released in 2007, Cuban communists felt a sense of vindication, finally gaining the ability to publicly accuse the United States government of what they claimed was already common knowledge.

In the summer of 1960, the CIA recruited former FBI agent Robert Maheu. He became the go-between from the agency to two prominent Italian gangsters on the FBI’s Ten Most Wanted List – Santo Trafficante of the Miami Syndicate, and Salvatore Giancana – Al Capone’s successor in Chicago. They were gotten hold of by way of Las Vegas mobster Johnny Roselli. A payment of $150,000 was on the table. According to the declassified documents, Giancana suggested using poisoned pills – six of them. But despite gaining access to officials inside the Cuban government, the plan had been unsuccessful, and was later scrapped in the run-up to the failed Bay of Pigs invasion. It is said the agency was able to retrieve all the poison pills.

The closest the Americans got to killing Castro was with a poisoned chocolate milkshake, Escalante claimed to Reuters. According to the 2007 documents, another batch of poison was delivered through the Mafia in 1963 in a bottle of Bayer aspirin pills. An opposition group, it was believed, had a good chance. But the plot failed when a disguised waiter did not manage to lace Castro’s milkshake in the cafeteria of the then-Hilton Hotel (now Havana Libre), as the pill got stuck in the freezer – where it was hidden – and broke apart when the assassin attempted to dislodge it from the wall.

2) Contaminating an entire broadcast studio with LSD with the intention of eroding public trust

This was not just about spiking drinks or cigars. The CIA went all-out. After a failed attempt to embarrass El Comandante by having his beard fall out due to boots spiked with chemicals, the agency had opted for a box of cigars spiked with LSD. The plan was to have Castro burst into laughter during a televised interview, thus subjecting him to ridicule in the public eye. But it was not just cigars. The CIA planned to lace the entire studio. This plot was not implemented, but was high in the running for ways to spark a national uprising against Castro.

3) Tuberculosis-laced scuba gear that followed the exploding sea shell 

The CIA had back-paddled on another of its ingenious plans to kill Castro, leading to the poisoned scuba gear idea. The agency knew the revolutionary was an avid diver. The plan had been to attract El Comandante with a sea shell practically impossible to miss, having been painted in colors bright enough to attract him. Castro would swim closer to inspect it, whereupon a lethal amount of explosives would detonate. But the idea was aborted due to impracticality, the declassified documents claimed. So the spies went the more practical way: lacing Castro’s scuba gear with tuberculosis to trigger a deadly skin disease. The man who was supposed to give Castro the suit had opted to give him an ordinary one, it turned out. 

4) Evolution of the poison cigar – the exploding cigar

According to a Saturday Evening Post report on November 4, 1967, a CIA agent had approached a New York cop with the idea of handing Castro an exploding cigar during a UN meeting. That was reportedly after the plan to poison the cigar had been abandoned. This was despite the poison having already been injected into the cigar, with the CIA dismissing the person tasked with carrying the plan out in the final stages.

However, the exploding-cigar plan also failed due to the double agent changing his mind at the last instant. 

5) Femme fatale