The Plots to Kill Castro

The Cuban Revolution and a Hostile Washington

On January 1, 1959, Fidel Castro's rebels forced the dictator Batista to flee, and Castro took power in Cuba. As his government nationalized American property and drew closer to the Soviet Union, relations collapsed; the United States severed diplomatic ties in January 1961.

Why it matters: Ninety miles from Florida, a communist ally of Moscow now ruled Cuba. To Cold War Washington, removing Castro became an urgent priority — by any means.

‘A Sensitive Mission’: The CIA Decides to Kill Castro

By 1960 the CIA had begun planning not just to overthrow Castro but to assassinate him. The agency's deputy director for plans, Richard Bissell, authorized what one memo called 'a sensitive mission requiring gangster-type action' — the 'liquidation of Fidel Castro.'

Why it matters: This marked the start of a years-long secret program of assassination plots that a US Senate committee would later expose as some of the darkest work of the Cold War CIA.

Sidney Gottlieb and the CIA's Poison Lab

Many of the plots' weapons came from one man: Sidney Gottlieb, the chemist who ran the CIA's Technical Services Division and its notorious MKULTRA mind-control program. His lab devised the botulinum toxins, treated cigars and disease-causing agents intended for Castro.

Why it matters: Gottlieb's shadowy laboratory was the technical heart of the campaign — where the CIA's strangest assassination weapons were actually created.

The Depilatory Plot: Making Castro's Beard Fall Out

One scheme aimed not to kill Castro but to humiliate him: dusting his shoes with thallium salts so that his iconic beard would fall out, wrecking the rugged image at the center of his revolutionary appeal.

Why it matters: The 'depilatory' plot reveals how badly the CIA misjudged Castro — imagining his power could be undone by ruining his beard.

LSD in the Radio Studio

In another discrediting scheme, the CIA considered spraying the broadcasting studio where Castro was to appear with an aerosol of LSD, hoping the hallucinogen would make him rant incoherently on live radio.

Why it matters: Like the beard plot, the LSD scheme aimed to destroy Castro's authority rather than his life — psychological warfare from the same labs that brewed the poisons.

The Poison Cigars

In one plot the CIA had a box of Castro's favorite cigars laced with botulinum toxin so potent that merely putting one in his mouth would be fatal. The poisoned cigars were reportedly passed to an intermediary in early 1961; what became of them is unknown.

Why it matters: The poisoned cigar became the most iconic image of the CIA's campaign against Castro — improbable, but entirely real.

The CIA Hires the Mafia

The CIA turned to organized crime, using go-between Robert Maheu to recruit mobsters — including Sam Giancana, Johnny Roselli and Santo Trafficante — to arrange Castro's murder. The mob, which had lost lucrative Havana casinos to the revolution, was a willing partner.

Why it matters: The government secretly partnering with the Mafia to kill a foreign head of state was among the most explosive revelations when the plots later came to light.

Marita Lorenz and the Cold-Cream Capsules

By her own later account, Marita Lorenz — a young German-American woman who had had an affair with Castro — was recruited by the CIA to poison him with capsules she hid in a jar of cold cream. She said she lost her nerve, and that Castro, sensing the plot, handed her a gun which she could not use.

Why it matters: The 'femme fatale' plot became one of the most sensational episodes of the whole saga, though it rests largely on Lorenz's own colorful and contested testimony.

How we know: The account comes chiefly from Lorenz's own later interviews and memoirs, and elements of her story have been questioned.

A Plot to Kill Raúl Castro

Fidel was not the only Castro in the CIA's sights. In 1960 the agency approved a plot to assassinate his brother Raúl, offering a recruited Cuban pilot a payment to arrange a fatal 'accident.' The order was hurriedly rescinded before it could be carried out.

Why it matters: The Raúl plot, documented in the CIA's own declassified cables, shows the assassination campaign reached beyond Fidel to the wider revolutionary leadership.

The Poison Pills

The CIA's Technical Services Division produced poison pills of botulinum toxin — six in all — designed to dissolve in Castro's food or drink. They were passed through Mafia contacts to Cubans who were supposed to slip them to Castro, but the plots repeatedly fell through.

Why it matters: The poison-pill plots, run in tandem with the Bay of Pigs preparations, are among the plots most firmly documented in the CIA's own records.

The Bay of Pigs

In April 1961 the CIA launched the Bay of Pigs invasion, landing a force of Cuban exiles to topple Castro. It was a total failure: the exiles were quickly defeated and captured, humiliating the new Kennedy administration.

Why it matters: The disaster hardened Washington's obsession with Castro. Rather than abandon the effort, Kennedy's team redoubled it through covert action — and the assassination plots pressed on.

Veciana's Bazooka Plot

In October 1961 the Cuban exile Antonio Veciana — working under a mysterious CIA handler he knew as 'Maurice Bishop' — plotted to kill Castro with a bazooka fired from an apartment overlooking the Presidential Palace in Havana. The gunmen lost their nerve as Castro's security flooded the area.

Why it matters: The bazooka plot launched a parallel campaign: exile militants, armed and trained by the CIA, who would hunt Castro for decades after the agency's own plots wound down.

Operation Mongoose

After the Bay of Pigs, the Kennedys launched Operation Mongoose, an aggressive covert campaign of sabotage and subversion aimed at bringing down Castro's government, run from the CIA's giant Miami station and overseen with the personal involvement of Attorney General Robert Kennedy.

Why it matters: Mongoose intensified the secret war on Cuba and kept the assassination plots alive, forming the backdrop to the tensions that led to the Cuban Missile Crisis.

The Cuban Missile Crisis

The relentless pressure — the Bay of Pigs, Operation Mongoose and the assassination plots — helped drive Castro into the arms of Moscow. In October 1962 the discovery of Soviet nuclear missiles in Cuba brought the world to the brink of nuclear war.

Why it matters: The campaign against Castro was not cost-free: it helped provoke the most dangerous confrontation of the entire Cold War.

The Poisoned Milkshake

In 1963, working again through the Mafia, the CIA had a waiter at the Havana Libre hotel drop a botulinum capsule into Castro's regular chocolate milkshake. The capsule had frozen to the inside of a freezer where it was hidden and broke apart when the waiter tried to pry it loose.

Why it matters: Cuba's own longtime security chief later called the frozen milkshake the single closest the CIA ever came to actually killing Fidel Castro.

The Contaminated Diving Suit

Knowing Castro loved to scuba dive, the CIA plotted to give him a diving suit dusted inside with a fungus to cause a chronic skin disease, and a breathing apparatus contaminated with tuberculosis bacteria. It was to be handed over by the American lawyer James Donovan during hostage negotiations.

Why it matters: The poisoned wetsuit is a textbook example of the CIA exploiting Castro's personal habits — and of how elaborate the plots had become.

The Exploding Seashell

In another scheme built around Castro's love of diving, the CIA considered packing a large, brightly painted seashell with explosives and placing it on the seabed where he liked to dive, hoping he would swim over to inspect it. The idea was abandoned as impractical.

Why it matters: Later confirmed in declassified JFK-assassination files, the exploding seashell became a byword for the sheer creative desperation of the campaign to kill Castro.

The Poison Pen and the Day Kennedy Died

The CIA cultivated a high-level Cuban official, code-named AM/LASH (later identified as Rolando Cubela), to kill Castro. On November 22, 1963 — the very day President Kennedy was assassinated in Dallas — a CIA officer in Paris handed Cubela a poison pen fitted with a fine hypodermic needle.

Why it matters: The extraordinary coincidence — a CIA plot to kill Castro advancing at the exact hour Kennedy was murdered — has fueled speculation and investigation ever since.

The AM/LASH Files: Cubela's Long Plot

For years the CIA cultivated the disillusioned Cuban major Rolando Cubela — AM/LASH — as an inside assassin. Beyond the 1963 poison pen, the agency offered him rifles with telescopic sights to shoot Castro. Cuban security eventually uncovered the plot, and Cubela was arrested in 1966.

Why it matters: The AM/LASH files document the CIA's most sustained and serious effort to have Castro killed from within his own government.

How we know: Detailed in the CIA Inspector General's 1967 report, later published in the State Department's Foreign Relations of the United States series.

Alpha 66 and the Exile Raiders

After fleeing Cuba, Veciana founded Alpha 66, one of the most militant Cuban-exile paramilitary groups. From bases in the United States it launched armed raids on Cuba for years, part of a shadow war waged by exiles — many of them CIA-trained — who never stopped trying to kill Castro.

Why it matters: As the CIA's official plots faded, the exile groups it had armed carried the campaign forward, keeping Castro a hunted man for decades.

Drew Pearson's Column and the CIA's Secret Report

In March 1967 the columnist Drew Pearson publicly alleged that the CIA had plotted to kill Castro. A rattled President Johnson ordered the agency to investigate itself, producing Inspector General John Earman's secret 1967 report — the most detailed internal accounting of the plots ever written.

Why it matters: The Earman report, kept classified for decades, became the authoritative record when Congress and historians finally forced the plots into the open.

The CIA and the Death of Che

The hunt extended to Castro's comrade-in-arms. In October 1967 Che Guevara, leading a guerrilla campaign in Bolivia, was captured by a US-trained Bolivian battalion with the CIA officer Félix Rodríguez on the scene. On orders from the Bolivian high command, he was executed the next day.

Why it matters: If the CIA never got Fidel, it helped get Che — a reminder that the secret war targeted the revolution's whole leadership, not just its figurehead.

The Church Committee Exposes the Plots

In 1975 the US Senate's Church Committee investigated CIA abuses and published 'Alleged Assassination Plots Involving Foreign Leaders,' finding concrete evidence of at least eight CIA plots to kill Castro between 1960 and 1965. It could not establish that any president had directly ordered the killings.

Why it matters: The report confirmed the plots as official fact for the first time, and its revelations helped drive sweeping intelligence reforms.

Executive Order 11905: Ford Bans Assassination

The exposure of the Castro plots produced a landmark reform. On February 18, 1976, President Gerald Ford signed Executive Order 11905, declaring that 'no employee of the United States Government shall engage in, or conspire to engage in, political assassination.'

Why it matters: For the first time the United States formally banned the very kind of assassination plotting it had aimed at Castro — a prohibition reaffirmed by every president since.

Veciana and the Kennedy Connection

Antonio Veciana later made an explosive claim: that in 1963 he saw his CIA handler 'Maurice Bishop' meeting with Lee Harvey Oswald, months before Oswald allegedly shot President Kennedy. Investigators came to identify 'Bishop' as the veteran CIA officer David Atlee Phillips, who denied it.

Why it matters: The claim ties the Castro plots to the enduring mysteries of the Kennedy assassination — and to suspicions that the secret war on Cuba somehow rebounded on Dallas.

How we know: The account rests on Veciana's own testimony, which he maintained for decades but which Phillips and others disputed.

Luis Posada Carriles: The Exile Assassin

Luis Posada Carriles was the archetype of the CIA-trained exile: recruited and schooled by the agency in the 1960s, he spent the rest of his life plotting against Castro and Cuba, tied to bombings and assassination schemes across the hemisphere while repeatedly evading justice.

Why it matters: Posada embodied the long afterlife of the CIA's secret war — a militant the agency had created who pursued Castro for over forty years.

The Wasp Network: Havana's Spies in Miami

Castro's survival owed much to his own spies. In the 1990s Cuba ran the 'Wasp Network,' agents who infiltrated Miami exile groups such as Alpha 66 and Brothers to the Rescue to detect plots. The FBI arrested five of them in 1998 — the 'Cuban Five' — in a case that became a cause célèbre in Havana.

Why it matters: The Wasp Network shows why so many plots failed: Cuban intelligence had penetrated the very exile groups trying to kill Castro.

The 2000 Panama Summit Plot

In November 2000, as Castro attended a summit in Panama, Posada and three accomplices were caught with a large cache of explosives in a plot linked to a University of Panama auditorium where he was to address students. Castro publicly exposed the scheme; the men were convicted, then controversially pardoned in 2004.

Why it matters: The Panama plot, four decades after the first poison cigars, showed that the campaign to kill Castro outlived the Cold War itself.

Cuba's Count: 638 Alleged Plots

Fabián Escalante, the former head of Cuba's counterintelligence tasked with protecting Castro, claimed there had been some 638 plots and schemes to kill him over the decades (634 in his book) — a figure popularized by the 2006 documentary '638 Ways to Kill Castro.'

Why it matters: The '638' number became legendary, capturing the sheer scale of the effort — even as it vastly exceeds the eight plots the United States has officially confirmed.

How we know: The figure comes from Cuban intelligence sources and cannot be independently verified; it is far higher than the number substantiated by US investigations.

The Family Jewels

In 2007 the CIA declassified the 'Family Jewels,' a long-secret internal compilation of the agency's most controversial activities. Among them was the record of the CIA-Mafia collaboration to assassinate Castro, confirming details the agency had guarded for decades.

Why it matters: The Family Jewels laid bare, in the CIA's own words, that the plots to kill Castro were not rumor but documented agency operations.

How Castro Survived: The Gold Medal

By his 90th birthday, Cuba's spy chief Fabián Escalante had catalogued hundreds of attempts on Castro's life, foiled by counterintelligence, incompetence and luck. Castro himself liked to joke: 'If surviving assassination attempts were an Olympic event, I would win the gold medal.'

Why it matters: That the target of so many schemes died in his bed became a defining part of Castro's legend — and a lasting humiliation for the agency that tried to kill him.

Castro Outlives Them All

Fidel Castro died of natural causes on November 25, 2016, at the age of 90. He had ruled Cuba for nearly half a century and outlasted ten US presidents — dying, in the end, not by any plot but of old age.

Why it matters: That the target of so many assassination schemes died peacefully at 90 is the saga's final irony — and the reason the plots are remembered as much for their failure as their audacity.