How Fidel Castro Survived 638 Very Bizarre Assassination Attempts
- Daniel Holland
- 7 hours ago
- 8 min read
It is one of those claims that sounds too extravagant to be true, yet stubbornly refuses to disappear. In 2006, Fabián Escalante, the former head of Cuban counter intelligence, sat down with a British documentary team and calmly stated that the United States Central Intelligence Agency had tried to kill Fidel Castro more than 600 times over the course of roughly four decades. Not dozens. Not even hundreds. More than 600.
Escalante spoke without theatrical flourish. For him, assassination attempts were not rumours or propaganda talking points, but a routine feature of his professional life. As a senior figure in Cuba’s security apparatus, he had spent years analysing threats, intercepting plots, and reconstructing the intentions of foreign intelligence agencies. Yet even for seasoned Cold War observers, the number raised eyebrows. Six hundred assassination attempts felt closer to myth than history.
The truth, as it often does, sits somewhere between exaggeration and bureaucratic reality.
The origins of a lethal obsession
The hostility between Washington and Havana did not emerge slowly. It arrived with speed and intensity after Castro’s 1959 revolution swept away the US backed Batista regime. Almost overnight, American business interests were nationalised, organised crime lost its lucrative Cuban casinos, and the Caribbean gained a socialist government openly aligned with the Soviet Union.
For US policymakers in the early 1960s, Castro was not simply a foreign leader with an opposing ideology. He was viewed as a contagious symbol. A successful revolution ninety miles from Florida threatened to inspire similar movements across Latin America. Removing him became a strategic goal, pursued through sanctions, sabotage, propaganda, and covert action.
Assassination was discussed early, even if rarely admitted publicly.
Declassified CIA records show that by 1960 the agency was already exploring ways to eliminate Castro without leaving fingerprints. Internal memoranda spoke euphemistically of “executive action” and “gangster type operations”. The language itself reflected a mindset shaped by deniability rather than morality.
Mobsters, poisons, and plausible deniability
One of the most extraordinary chapters in this history involves the CIA’s willingness to collaborate with organised crime figures. At the time, American Mafia leaders were nursing deep grievances against Castro. His closure of Havana’s casinos had wiped out millions in revenue. Their interests briefly aligned with those of the US government.
CIA officials met with prominent mob figures and intermediaries connected to Cuban contacts willing to attempt an assassination. The preferred method, according to agency documents, was poisoning. Firearms were considered too public, too messy. A discreet death would be easier to explain away.
One CIA report records an operative suggesting that a “potent pill” placed in Castro’s food or drink would be the most effective approach. Botulism capsules were supplied. Weeks passed. Nerves set in. The would be assassin withdrew. A second operative also failed to act. Eventually, the CIA retrieved the poison pills and quietly closed the operation.
These episodes reveal something important. Many assassination attempts never progressed beyond planning. Others collapsed under the weight of human fear. It is one thing to discuss killing a head of state in a briefing room. It is quite another to slip poison into the meal of a heavily guarded revolutionary leader.
From cloak and dagger to cartoon logic
As the years went on, the schemes grew stranger. This is where the story begins to resemble parody, and where comparisons to Wile E. Coyote or a satirical James Bond film are often made. Yet the documents are real, and the proposals were seriously discussed.
Among the ideas examined by the CIA and later exposed by congressional investigations were:
An exploding cigar, designed to detonate when Castro smoked it. A contaminated wetsuit, laced with a fungus intended to cause a debilitating skin infection. A diving mask dusted with botulismA booby trapped seashell placed in an area where Castro was known to dive
Some plots appear to have originated from technical staff eager to apply ingenuity to geopolitical problems. Others likely reflected a culture in which creative thinking was encouraged, even when detached from practical reality. Few of these plans moved beyond early stages. Several were abandoned as unworkable. Some were never attempted at all.
But their existence tells us something about the internal culture of Cold War intelligence agencies. With vast resources, minimal oversight, and a perceived existential threat, extraordinary ideas could circulate with surprising momentum.
Congressional reckoning and the Church Committee
By the mid 1970s, the secrecy surrounding US intelligence operations began to unravel. Investigative journalists uncovered evidence of surveillance abuses, covert interventions, and assassination plots targeting foreign leaders.
The resulting scandal led to the creation of the Church Committee, a Senate investigation tasked with examining abuses of power by US intelligence agencies.
Its findings were stark.
The committee concluded that there was “concrete evidence of at least eight plots involving the CIA to assassinate Fidel Castro between 1960 and 1965”. These were not speculative ideas scribbled on notepads, but credible operations involving weapons, poisons, and coordination with external actors.
The report stated that the proposed assassination devices “strained the imagination”, a phrase that has since become inseparable from this chapter of Cold War history. It also revealed that before resorting to lethal measures, the CIA had explored humiliating alternatives, including attempts to make Castro’s beard fall out or to chemically disrupt his speech during radio broadcasts.
These efforts reflected a belief that undermining Castro’s image could weaken his authority. When such schemes failed, more direct options returned to the table.
In response to the committee’s revelations, President Gerald Ford issued an executive order in 1976 banning political assassinations. It was an attempt to draw a line under the most controversial practices of the Cold War.
Castro’s own tally
In 1975, Castro himself submitted a list of 24 assassination attempts he claimed were sponsored by the United States. The Church Committee examined these claims and concluded that none of those specific incidents could be verified. Instead, investigators identified eight other plots they considered credible.
This discrepancy highlights the difficulty of counting assassination attempts. What qualifies as an attempt? A fully operational plan? A proposal that reached senior approval? An idea never acted upon? Escalante’s figure of 600 almost certainly included everything from serious plots to half formed schemes discussed and discarded.
In that sense, the number may tell us less about how many times Castro nearly died, and more about how frequently US intelligence returned to the idea of killing him.
Violence beyond the ban
Despite the 1976 executive order, violence surrounding Castro did not entirely cease. In 2000, former CIA operative Luis Posada Carriles was arrested in Panama and charged with planting explosives beneath a podium where Castro was scheduled to speak at a summit.
Castro’s security team discovered the explosives in time. Posada was later pardoned in 2004 by Panamanian President Mireya Moscoso and fled to the United States. His past cast a long shadow. Posada had long been linked to the 1976 bombing of a Cubana airliner that killed 73 people, including members of the Cuban national fencing team.
These later plots complicate the idea that assassination attempts ended neatly with Ford’s order. They suggest a murkier reality, where deniable actors and former operatives continued to operate in the margins.
A tale of obsession and irony
Perhaps the most unsettling aspect of this history is its duration. According to Escalante, the administration of John F. Kennedy alone authorised 42 attempts on Castro’s life. Yet Kennedy himself was assassinated in Dallas in 1963, a reminder that violence has a way of rebounding in unpredictable ways.
For all the resources devoted to eliminating Castro, he outlived ten US presidents and died of natural causes in 2016. The man portrayed for decades as an existential threat proved remarkably durable, both politically and physically.
What remains is not simply a catalogue of failed plots, but a portrait of a bureaucracy operating with immense power and limited restraint. The repeated attempts to kill Castro reveal how myth, fear, and ideology can distort decision making, producing actions that appear absurd in hindsight but felt urgent at the time.
Escalante’s claim of 600 attempts may never be proven in any strict numerical sense. Yet when viewed as a measure of obsession rather than arithmetic, it captures something undeniably real. For decades, the idea of killing Fidel Castro never fully left the minds of those tasked with confronting him. That persistence, more than any exploding cigar, may be the most revealing detail of all.
For anyone that cares, here's my favourite 5 attempts on Fidel Castro's life...
1. Exploding Cigar
Where: New York
When: 1966
Who: Police officer
How: A newspaper reported in 1967 that a year earlier the CIA had approached a New York City police officer with the idea of slipping Castro a cigar packed with enough explosives to take his head off. This has never been confirmed, though we know the CIA did use cigars for another, separate assassination attempt. In 1960, the CIA laced a box of Castro's favourite kind of cigars with poison, but the package never made it to Castro.
Close but no cigar.
2. Mafia ice cream surprise
Where: Havana
When: 1961
Who: Waiter
How: Castro loved ice cream as he loved cigars, and the CIA hit upon a plan to poison his dessert. To do this, they asked for help from the casino mafia who had been kicked off the island after Castro took power and outlawed gambling. According to some accounts, the mafia was able to slip a jar of poison pills to a cafe worker in the capital of Havana.
Some say the worker was meant to slip the poison into an ice cream cone, other say it was a milkshake. But at the crucial moment, the poison could not be dislodged from inside the freezer. It was frozen stuck.
Either way, this was the closest the CIA came to getting the marked man.
3. Exploding seashell
Where: Under the sea
When: 1963
Who: A Commie-hating mollusc
How: Castro loved diving as he loved cigars and ice cream, and the CIA looked into the idea of luring him to his doom with a large, brightly painted sea shell packed with explosives. It would be rigged to explode and then dropped in an area where Castro commonly went diving. The CIA purchased a large number of shells for this purpose, but there's no evidence the weaponised marine life were ever deployed.
4. Flesh-eating wetsuit
Where: Under the sea, slowly
When: 1961
Who: Lawyer
How: This plan got quite far. The gadgets arm of the CIA dusted the inside of a diving suit with fungus that caused a chronic skin disease, and put tuberculosis in the breathing apparatus. All they needed to do now was get Castro to put it on. It was decided a high-profile American lawyer who had been leading negotiations with Castro would become their unwitting accomplice, and present the suit to the Cuban leader. The plan fell apart when the man was tipped off by a CIA lawyer.
5. Character assassination
Where: On air
When: 1960
Who: The periodic table
How: The idea was to undermine Castro's public image by making him behave strangely while he was speaking to the nation. To do this, they would spray the radio broadcasting studio with a chemical similar to LSD, so that he would hallucinate on air. Another idea was to give him a box of cigars that would temporarily disorient him while he was giving a speech on television. Yet another scheme was to dust the inside of Castro's shoes with a chemical that would make his iconic beard fall out.
In the end, Fidel had the good fortune of growing old, bearded and not tripping balls.
