On January 1, 1959, troops of the revolutionary 26th of July Movement marched into the Cuban capital of Havana, toppling the American-backed government of dictator Fulgencio Batista. Two weeks later, the leader of the revolution, former lawyer Fidel Castro, was sworn in as Prime Minister. Almost immediately, Castro began implementing a program of sweeping socialist reforms, nationalizing Cuba’s sugar and oil refining industries, confiscating land from private owners and redistributing it among the peasantry, and seeking closer diplomatic and economic ties with the Soviet Union. These actions incensed and frightened the United States, who saw the Caribbean island as a dangerous communist outpost in the Western Hemisphere. Over the next six decades, Cuba’s beard-sporting, fatigues-wearing, cigar-chomping leader would remain a veritable obsession of the American CIA, attracting dozens of coup and assassination attempts. But while some of these plots were well-organized and came lose to succeeding, others were so improbably absurd they sound like something Wile E. Coyote would dream up after browsing the Acme Products catalogue – involving such exotic killing methods as exploding seashells, poisoned diving suits, and LSD-laced cigars. This is the story of the of the many hilarious ways the CIA tried – and failed – to kill Fidel Castro.

The first recorded attempt to undermine the Cuban revolution took place in early 1960, a year after the fall of the Batista government. According to former U.S. Air Force Colonel L. Fletcher Prouty, who revealed the plot in 1975, the U.S. Defense Department’s Office of Special Operations chartered a small Air Force liaison aircraft to fly two CIA-trained Cuban exiles from Elgin Air Force Base in Florida to a road just outside Havana. The exiles planned to infiltrate a building in Havana overlooking Castro’s daily commute and assassinate the leader with a sniper rifle. But while the plane returned safely to Florida, the two operatives were never heard from again, having likely been captured by Cuban forces en route to Havana.

Finding it increasingly difficult to infiltrate outside agents into Cuba, the CIA enlisted the help of a person with very close ties to Fidel Castro: his former mistress Marita Lorenz. The German-born daughter of an ocean liner captain, Lorenz arrived in Havana in February 1959 and soon met and began an affair with the new Cuban leader – who immediately proceeded to knock her up. Seven months later, Lorenz was given a glass of drugged milk, passed out, and awoke in a local clinic with her baby nowhere to be found. Shortly thereafter, she was recruited by CIA agent Frank Sturgis, who gave her a package of poison capsules and convinced her to return to Cuba and kill her former lover. Unfortunately, the plan immediately went awry. Paranoid that the pills would be discovered by Cuban customs, Lorenz hid them in a pot of cold cream. Later, when she tried to recover them:

“…they were all gunked up. I fished them out and flushed them down the bidet.”

Things only got worse when Castro finally appeared, as Lorenz later recalled:

“‘Why did you leave so suddenly?’ he asked. “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.’ He asked if I was working for the CIA. 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.”

Shortly after this encounter, Lorenz left Cuba, only returning once to visit Castro in 1981.

The CIA’s next major assassination attempt targeted not Fidel Castro but his younger brother Raúl, then leader of the Cuban Armed Forces. In July 1960, José Raúl Martínez, a pilot for national airline Cubana and secret CIA operative, revealed that he had been chosen to fly Raúl Castro to a meeting in Prague, in the then-communist republic of Czechoslovakia. Seizing a rare opportunity to eliminate a key figure in the Cuban government, the CIA wired $10,000 to William Murray, its operative in Havana, and instructed him to arrange for Castro to have an “accident.” The plot was a rush job in the extreme; indeed, Murray’s only chance to discuss the mission with Martínez was while the pilot was driving to the airport. And while Martínez was eager to eliminate Castro, he was unsure of how to do so without also killing everyone on the plane. In the end, he asked Murray:

“If I die, will you make sure that my two sons have their college education paid for?”

The CIA agreed, and Martínez set off on his mission. Minutes later, however, Murray received new orders: Do not pursue. Would like to drop matter. But it was already too late; the plane had already taken off, and Murray had no means of contacting Martínez. In the end, however, Martínez found no opportunity to arrange the CIA’s desired “accident”, and returned Raúl Castro to Cuba, safe and sound. A few months later, Martínez defected to the United States.

Just one month after this hastily-organized assassination attempt, the CIA concocted a more sophisticated scheme to poison Fidel Castro by contaminating his favourite cigars with botulinum toxin – one of the most powerful poisons known to science. According to official reports from the CIA’s Technical Services Division, the poisoned cigars were ready by October 7, 1960 and delivered to an unidentified operative in Cuba on February 13, 1961. For unknown reasons, however, the cigars never made it into Castro’s hands. At around the same time, the CIA also toyed with the idea of overthrowing Castro not by assassinating him, but by undermining his credibility. One such scheme involved clandestinely dosing Castro with LSD or a similar hallucinogen prior to his delivering a television or radio broadcast to make him behave erratically. Another plot, timed to coincide with a planned address before the United Nations in New York, involved poisoning Castro with Thallium salts. The salts, which would be slipped into Castro’s shoes when he set them outside his hotel room to be polished, would, it was hoped, cause Castro’s iconic beard to fall out, making him look weak on the world stage.. In the end, however, neither plan was carried out.

The next offensive against Cuba would be a much more substantial affair. In March of 1960, U.S. President Dwight D Eisenhower authorized the CIA to arm and train a force of exiled counter-revolutionaries to land in Cuba and lead a coup against the Castro government. Though Eisenhower left office later that year, his successor, John F. Kennedy, gave the operation the go-ahead. On April 17, 1961, a force of 1,400 Cuban exiles known as Brigade 2506, sailing from bases in Guatemala and Nicaragua, landed in the Bay of Pigs in southwest Cuba. The operation was a complete disaster. Due to confusion over time zones, the expected American air support came an hour late, and Brigade 2506 found itself pinned down on the beach by Cuban revolutionary forces. And when the world learned of the illegal invasion, President Kennedy cancelled further airstrikes. Within two days 100 exiles were killed and the rest captured. The Bay of Pigs Invasion was a major embarrassment for the Kennedy Administration, further souring relations between the United States and Cuba. In late 1961, Fidel Castro officially declared himself a Marxist-Leninist and publicly sought closer cooperation with Soviet Premier Nikita Khrushchev.

In the wake of the Bay of Pigs disaster, the CIA and Department of Defense launched Operation Mongoose, a multi-phase, coordinated program of military and intelligence operations designed to undermine and topple the Cuban government. The plan, authorized by President Kennedy on November 30, 1961, included the dissemination of anti-Castro propaganda, the training and infiltration of counter-revolutionary guerrilla units into the country, the assassination of key government figures, and:

“…all other political, economic and covert actions, short of inspiring a revolt in Cuba or developing the need for US armed intervention… in order to help Cuba overthrow the Communist regime…while [remaining] consistent with US overt policy, and [remaining] in position to disengage with minimum of loss in assets and US prestige.”

Operation Mongoose was placed under the directorship of CIA operative Edward Lonsdale, and given an initial budget of $100 million. Over the next two decades, the project would consume $50 million per year and involve some 2,500 Cuban and American personnel.

In June 1962, American lawyer James B. Donovan – most famous for arranging the exchange of Soviet spy Rudolf Abel for CIA pilot Francis Gary Powers – was sent to Cuba to negotiate the release of the 1,113 Cuban exiles taken prisoner during the Bay of Pigs invasion. In the lead-up to the mission, the CIA prepared a special scuba diving outfit which Donovan was to present to Castro as a gift. The wetsuit had been treated with spores of the fungus Eumycetoma, which causes the disfiguring skin disease Madura Foot, while the breathing apparatus was infected with tuberculosis bacteria. But in another stroke of bad luck, Donovan revealed that he had already gifted Castro with a diving suit, and the infected suit never left the United States. In the end, Donovan managed to secure the prisoners’ release in exchange for $52 million in medical supplies and baby food.

With their assets in Cuba swiftly dwindling, the CIA next turned to another group with a major grudge against Castro: the American Mafia. Prior to the revolution, the Mafia had enjoyed a lucrative presence in Cuba, running a chain of successful hotels, nightclubs, brothels, and casinos catering mostly to American tourists. When Castro came to power, however, he seized the Mafia’s assets and expelled them from the country. The CIA’s collaboration with the Mafia had begun back in 1960, when the agency sent former FBI agent and private intelligence contractor Bob Maheu to make contact with Chicago mob bosses Johnny Rosselli, Salvatore Giancana, and Santos Trafficant. The mobsters eagerly agreed to cooperate, even waiving their regular fee to carry out the assassination. Despite this, Maheu soon dropped out of the plot, later stating:

“I was not very happy about the project in the first place. I felt that I was building up my business, I had a good business going, the demands on behalf of the [Howard] Hughes interests were increasing progressively. On the other hand, I felt that I had an obligation to my country, and I recognized the fact that the Agency had been good to me in the early stages of my business. . . . I was anxious to get back to work. My recollection is that I phased out of the project as soon as it could be accomplished after the Bay of Pigs, or after the invasion was not successful.”

Rosselli, Giancana, and Trafficant, however, carried on plotting, and in 1963 they managed to smuggle a batch of botulinum toxin pills into Cuba, disguised in a bottle of aspirin. The perfect opportunity to deploy them soon arrived when Castro visited the Havana Libre Hotel, which served his favourite chocolate milkshakes. Interestingly, Castro was such an ice cream aficionado that in 1966 he spearheaded the construction of Havana’s famous Coppelia, a massive ice cream parlour which seated 1,000 guests and served a then impressive 26 different flavours. Yet despite the mob having found the perfect delivery mechanism for Castro’s poison, once again the plot quickly unraveled. When the would-be assassin went to retrieve the poison capsule from the freezer where he had hidden it, he found it frozen to the wall. His attempts to free the capsule caused it to rupture, scuppering the assassination attempt. It was the closest they came to actually killing Fidel Castro.

But this failure was not for lack of trying, for over the next decade the agency would hatch a dizzying array of harebrained assassination schemes, each more outlandish than the next. One such plot involved planting a conch shell packed with explosives near a reef where Castro liked to scuba dive. The shell was even painted in bright colours to make it especially attractive. Other schemes involved blowing Castro’s head off with exploding cigars, pushing him into a vat of molten metal while he toured a steel mill, injecting him with a poison-tipped needle disguised in a pen, shooting him with a gun hidden in a television camera, or killing him with a grenade disguised as a baseball – another of Castro’s favourite pastimes.

Of course, none of these attempts proved successful, and in 1976 the findings of the Church Committee – a U.S. Senate group established to investigate abuses by the CIA, FBI, NSA, and IRS – prompted President Gerald Ford to pass a series of Intelligence Services reforms which, among other things, banned the assassination of foreign leaders. This effectively brought Operation Mongoose to an end. Like the Bay of Pigs Invasion, Mongoose had turned into an embarrassing failure for the U.S. Government, swallowing countless millions of dollars while accomplishing little of substance. Meanwhile, the U.S. government had found more effective ways of containing Cuban influence. Following the Cuban Missile Crisis in October 1962, the United States imposed a complete trade embargo against Cuba.

But while the CIA was no longer allowed to assassinate Castro directly, they continued to work with Cuban exiles and other anti-Castro forces. As recently as 2000, former CIA operative Luis Posada was arrested in Panama for planting explosives in a podium where Castro was scheduled to speak. Castro’s security detail found and removed the explosives, and Castro’s speech proceeded as planned. In 2004, Panamanian President Mireya Moscoso pardoned and released Posada, who subsequently fled to the United States.

According to former Cuban Intelligence officer Fabian Escalante, over his lifetime Fidel Castro survived a whopping 638 assassination attempts. This number, however, is highly debated, with declassified CIA records confirming only 8 officially-sanctioned plots. Nonetheless, Castro’s apparent invulnerability became a part of his public image, with the leader once claiming that:

“If surviving assassination attempts were an Olympic event, I would win the gold medal.”

On another occasion, Castro was offered a Galápagos tortoise as a gift. But upon learning it would live for 100 years or more, he declined the offer, quipping:

“That’s the problem with pets. You get attached to them and then they die on you.”

Indeed, for a man forever in the world’s crosshairs, Castro lived an astonishingly long life, with the leader stating on his 90th birthday that:

“Never would such an idea have occurred to me. It was not the fruit of any effort, it was the whim of fate. Soon I will be like all the rest.”

These words would prove prophetic, for three months later on November 25, 2016, Fidel Castro finally died – not from an exploding cigar or poison milkshake, but the killer that gets us all in the end: time.