Fidel Castro took power in Cuba on January 1, 1959. Within eighteen months, the CIA was trying to kill him.

Not informally. Not rogue. With presidential authorization, agency resources, and a budget. Under eight American presidents from Eisenhower to Clinton, the United States government ran what was arguably the longest sustained assassination program against a single foreign leader in modern history.

Fabián Escalante was Castro’s counterintelligence chief — the man whose entire career was dedicated to keeping Castro alive. When he retired, he estimated the total number of plots, schemes, and attempts at 638. He broke them down by administration: 38 under Eisenhower, 42 under Kennedy, 72 under Johnson, 184 under Nixon, 64 under Carter, 197 under Reagan, 16 under George H.W. Bush, 21 under Clinton. These are Cuban government figures. The 1975 Church Committee — the U.S. Senate’s own investigation — documented eight proven CIA attempts between 1960 and 1965. Both counts are real. They measure different things.

The Church Committee also published the methods.
The CIA poisoned a box of Castro’s favorite cigars with botulinum toxin in 1960 — strong enough to kill anyone who put one in their mouth. They were delivered to an unidentified person. Castro never smoked them. They tried to contaminate a cigar with a chemical that would disorient him before a televised speech. They tried to make his beard fall out by dusting thallium salts on his shoes, believing public humiliation would undermine his authority. Castro canceled the trip. They tried to dose him with LSD on live television.

The CIA’s head of Cuban operations, Desmond FitzGerald, bought two books on Caribbean mollusks researching which shell would be colorful enough to catch Castro’s eye on a dive — then fill it with explosives. The plan was described in the Church Committee report as “discarded as impractical.” They designed a diving suit contaminated with a fungus that would cause a chronic debilitating skin disease, meant to be handed to Castro by an American lawyer during hostage negotiations. The lawyer gave Castro a different suit.

They hired the Mafia.
Sam Giancana, boss of the Chicago mob, and Santos Trafficante, head of the mob’s Cuban operations, were contracted by the CIA to kill Castro for $150,000 — over a million dollars in today’s money. The Mafia had their own reasons. Castro had shut down their Havana casino operations when he took power. The CIA wanted deniability. The mob wanted their casinos back. The contract was documented in the Church Committee report. None of the attempts succeeded.

Escalante — Castro’s own intelligence chief — later said the closest anyone ever came was a hotel employee at the Havana Libre, bribed to put a poison capsule into Castro’s milkshake. The capsule had been stored in a freezer. It stuck to the ice tray. When the employee tried to retrieve it, it broke.
Castro survived because a capsule got stuck to ice.
On November 22, 1963, a CIA case officer in Paris handed a Cuban asset a hypodermic needle concealed in a ballpoint pen — the needle so fine that the victim would not feel its insertion. The meeting was underway at the exact moment President Kennedy was shot in Dallas. The Church Committee documented this. No one has ever fully explained the timing.

Castro quoted himself on survival: “If surviving assassination attempts were an Olympic sport, I would win the gold medal.”
He was not wrong. He died in Havana on November 25, 2016. He was 90 years old. Natural causes.
The 1975 Church Committee findings were so damaging that President Gerald Ford issued Executive Order 11905 the following year. It banned U.S. government political assassinations. The order remains in effect.

The seashell was never planted. The cigar was never smoked. The beard stayed on. The milkshake capsule stuck to the ice.
And the man they spent decades trying to kill outlived most of the people who tried.

Culled