Answer: Fidel Castro
Let’s cut through the mythology: plenty of world leaders have had someone try to kill them. Some had a couple attempts; some a handful; a few, more than seems statistically possible for a single lifetime. But the king of dodging bullets—literally and metaphorically—might just be Fidel Castro.
It almost sounds like a running joke: “How many times did someone try to assassinate Fidel Castro?” The number you hear tossed around by former U.S. officials and the Cuban regime itself is somewhere between at least 600 and 638 attempts—depending on who’s counting and what you consider a “real” attempt. Some were almost cartoonish: exploding cigars, poisoned diving suits, femme fatales with a pistol under the pillow. Some were straight out of a Cold War fever dream.
Let’s talk specifics, because this is where it gets wild: One plot involved giving Castro a diving suit contaminated with deadly spores, banking on his love of underwater exploration to do him in. Another time, a former lover, Marita Lorenz, was handed poison pills by the CIA, only to break down at the last second, overwhelmed by the surreal reality of killing the man she’d once loved. There’s the infamous exploding cigar—which sounds like something Bugs Bunny would dream up if he worked for the CIA. And, of course, there were mafia hitmen, sometimes contracted by the U.S. government itself, lurking in the background with their own motives, their own grudges.
But let’s widen the lens: Why did so many different people want this man dead? For the CIA, it was about stopping communism at America’s doorstep. For exiles, it was about vengeance and reclaiming a lost homeland. For the mafia, it was about getting their Havana casinos back. If you ever needed a case study in how ideology, money, and personal vendetta can intersect in the most combustible ways imaginable, Fidel Castro was it.
What does it do to a person to live like this? Castro never went anywhere the same way twice. He trusted almost no one, kept his inner circle in constant rotation, and slept in different places, always a step ahead of the next plot. The guy once said, “If surviving assassination attempts were an Olympic event, I would win the gold medal.” But behind the bravado, there’s a human cost. Imagine the anxiety, the fatigue, the impact on family, friends, and even allies—anyone close enough to be collateral damage. Was it paranoia if everyone really was out to get you? Or was it survival instinct, honed into an art form?
And then there’s the legend—this larger-than-life narrative of an invincible revolutionary. But let’s put on our skeptic hats for a moment: How much of this is true? Was it really over 600 attempts, or did the Cuban regime find value in stoking the myth of the indestructible leader? Did the U.S. really bungle that many plots, or was the legend itself a psychological weapon, making Castro appear immortal and untouchable to his enemies and people alike?
Castro’s survival didn’t just shape his leadership; it shaped how history remembers him. To some, he’s a cunning survivor who outlasted ten U.S. presidents. To others, he’s the architect of a surveillance state where trust was a liability. Maybe both are true. And maybe that’s the lesson—when the world tries to end your story so many times, the story itself becomes the shield. You stop being just a man, and start becoming a myth.
