The longtime Communist ruler of Cuba, Fidel Castro, once declared, “If surviving assassination attempts were an olympic event, I would have the gold metal.”

After the 1959 Revolution, Cuba’s rebel leader closed the country to free enterprise, drawing the ire of America’s Cold Warriors then combating Soviet influence across the globe. Deciding they could not tolerate the establishment of a Communist state 90 miles off the coast of Florida, John F. Kennedy and the CIA supported a large-scale amphibious assault on the island conducted by anti-communist Cuban refugees. Without air cover, however, the Bay of Pigs invasion of 1961 proved a military disaster and only succeeded in rallying the Cuban public behind Castro’s new government.

The CIA masterminded several more machinations against the cigar-chomping Communist, colluding not only with other anti-Castro factions in Cuba, but with mafia hitmen. After the Marxist despot boarded up the crime family-owned casinos along the beaches of Havana, mob bosses like Chicago’s Sam Giancana were eager to avenge the loss of their lucrative luxury resorts. In “Operation Mongoose,” underworld figures conspired with U.S. intelligence to poison Castro by various means, including the use of a syringe-like ballpoint pen, chemically-laced ice cream, and cigars substantially more toxic than typical tobacco.

For later plotters, the weapon of choice would be a cigar filled — not with poison — but explosives that would detonate when the stogie was held to a match. On another occasion, the CIA sought to bait the dictator, an avid seashell collector, with a particularly beautiful — and incendiary — conk placed on a Cuban beach. Castro’s love of the sea was again thought to be his Achilles heel when the CIA devised a plan to provide the revolutionary leader with a diving suit infected with a flesh-eating fungus.

Although most of the CIA’s schemes never progressed beyond the idea stage, according to Israel Behar, Castro’s former chief of counterespionage, Cuban agents were able to identify — and successfully infiltrate — at least 26 distinct assassination plots against the Cuban autocrat. In one instance, the womanizing Castro learned that a jealous lover, Martina Lorenz, had been recruited by the CIA to feed him poison pills. Rather than having her imprisoned, Castro personally confronted Lorenz. Handing the woman his gun, Castro said, “You can’t kill me. Nobody can kill me.” According to Lorenz, Castro “kind of smiled and chewed on his cigar. I felt deflated. He was so sure of me. He just grabbed me. We made love.”

Always one step ahead of the intrigues against him, Fidel Castro died of natural causes in 2016, outliving each of the U.S. Presidents who plotted his death.