Fidel Castro: 5 of the Most Bizarre Assassination Attempts

1. The Exploding Cigar

One of the most famous (and cartoonish) assassination attempts involved a cigar rigged with explosives. Knowing Castro’s love for Cuban cigars, the CIA considered slipping him one that would detonate in his face when lit.

While it’s unclear whether the plan progressed beyond the planning stages, it has become symbolic of the desperate and absurd lengths some were willing to go to. A separate plan involved contaminating cigars with botulinum toxin, one of the deadliest known poisons. That effort also failed, and Castro quit smoking altogether in 1985, rendering future cigar-based plots useless.

2. The Poisoned Diving Suit

As an avid scuba diver, Castro often explored the waters off Havana. The CIA tried to take advantage of this hobby by planting a diving suit contaminated with deadly fungus that would cause a debilitating skin disease. In another variation of this plan, the agency bought a large quantity of Caribbean molluscs, intending to load a shell with a lethal amount of explosives. The idea was that the molluscs would be painted in vivid colours to attract the attention of an underwater Castro. Neither plan made it to fruition.

3. A Lover’s Betrayal

In 1960, one of the most emotionally dramatic attempts involved Castro’s lover, Marita Lorenz. The CIA gave her poison capsules and instructed her to drop them into his drink. But when the moment came, Lorenz couldn’t go through with it. In a dramatic twist, she confessed the plot to Castro himself.

According to her later testimony, instead of being angry, Fidel seemed amused. He calmly handed her his pistol and said: “You can’t kill me. Nobody can kill me.”

4. Poisoned Milkshake

This attempt came remarkably close to succeeding, inside Havana’s Hotel Habana Libre. CIA agents recruited a waiter to poison Castro’s favourite chocolate milkshake. The poison pill was hidden in the freezer until it was time to be added to the drink. But as the moment approached, disaster struck: the capsule got stuck in the ice tray. When the waiter tried to pry it free, it broke open and became unusable.

It was a near-miss and became known as one of the better-documented failures.

5. Mafia Hitmen

In a truly bizarre alliance, the CIA reached out to the American Mafia in the early 1960s, believing their violent expertise might succeed where others had failed. Mobsters, including Sam Giancana and Santo Trafficante Jr., were offered large sums of money (up to $1.2 million in today’s money) and legal immunity to take out Castro.

Plans included poisoned pills slipped into food or drinks and orchestrated shootings, but none came close to success. The CIA’s collaboration with organised crime was ultimately derailed by poor planning, mutual suspicion, and a change in political climate as the Kennedy administration began backing away from more extreme measures.

As it turned out, the Mafia was no better at killing dictators than the CIA.

Conclusion

Despite endless plots, Fidel Castro survived them all, often with a mix of luck, vigilance, and sheer bravado. He stepped down voluntarily in 2008 and died peacefully in 2016 at the age of 90, having defied assassins for nearly half a century. In the end, Castro outlasted nearly every enemy who tried to kill him, and left behind one of the strangest legacies of political survival in modern history.