Some of us always believed the CIA would get Fidel Castro eventually. It’s been more than 50 years since Jack Kennedy’s administration started cooking up inventive ways to assassinate him, but so what? The stroke of genius was waiting until nobody this side of Madame Tussaud’s gave a damn. When our black-ops people are given a job to do, that job gets done, by golly.

In case you can’t tell whether I’m ridiculing Communism’s answer to Rip Van Winkle or the U.S. government’s Rip Van Uncle Sam obsession with deposing him—a vendetta that ended only last March with President Barack Obama’s visit to Havana—the truth is I’m happy doing both. Sorry, but solemn indictments and defenses of Castro’s unbelievably lengthy dictatorial rule over long-suffering Cuba, which clamped down on dissenters and made life hell for gays and other miscreants, can be found elsewhere. I’d rather remember how the Cold War turned a minor Caribbean despot’s regime into a tragicomic banana peel (also Cuba’s approximate shape on a map) that two rival superpowers spent years skidding on at their peril.

If Castro had had the good sense to die soon after his victorious rebels entered Havana in 1959 and ousted Fulgencio Batista—the kind of puppet only the United States could love—he’d be remembered as a romantic figure today. But he lost a lot of international good will by sticking hundreds of Batista’s subordinates in front of firing squads for executions merrily overseen by the more bloodthirsty Che Guevara.

He got his mojo back thanks to the botched Bay of Pigs invasion by U.S-backed Cuban exiles, which reframed Castro as the gutsy Marxist David to America’s blundering Goliath. That cult seduced any number of left-wing American and foreign intellectuals, who persisted in seeing him as heroic well after plenty of Cubans got tired of the myth they’d been drafted into. Even so, residual sentimentality about Castro sure beats glamorizing Guevara. The difference between them is the difference between King Lear and Sweeney Todd.

In American eyes, Castro’s worst sin was turning to the Soviet Union as his patron, but it was an alliance whose potential for mutual incomprehension was farcical from the get-go. He and then Soviet premier Nikita Khrushchev never made much sense of each other, partly because Castro’s vanity wouldn’t let him realize that Khrushchev didn’t really cherish him as a fellow revolutionary. He was just a geopolitical pawn.

Hence 1962’s Cuban Missile Crisis, a showdown that ended when Khrushchev agreed to swap withdrawing the missiles he had parked in Cuba for a U.S. pullout of its own missiles from Turkey. Quite possibly, that was the deal he’d had in mind all along—and that’s how you make use of geopolitical pawns. Castro never got over the betrayal; apparently, he believed the USSR was genuinely prepared to launch a nuclear war for Cuba’s sake. To his considerable embarrassment, he’d implored Khrushchev to push the button instead of turning tail.

Meanwhile, our spooks kept trying to bump him off, cooking up one loony plot after another: an exploding cigar, a bacillus-infected scuba-diving suit, a gift pen concealing a hypo. There were literally hundreds of schemes in this vein, and the most infamous ploy might be the one that involved depilatories that would cause Castro’s beard to fall out, discrediting him with virility-loving Cubans.

Pretty damn surprisingly, another hinged on staging the Second Coming of Christ, with a U.S. submarine firing a shell to mimic the Star of Bethlehem while “Jesus’s” voice broadcasted anti-Castro propaganda from the heavens. You’d have to be awfully humorless not to wish that one had made it past the drawing boards; only Joel and Ethan Coen could truly do it justice.

Once America got distracted by Vietnam, however, Castro lost his status as our number-one nemesis. It must have grieved him since that role was vital to his international cachet. He did try to recapture our wandering attention from time to time, with stunts ranging from trying to rerun the missile crisis by allowing a Soviet combat brigade into Cuba (even Jimmy Carter wasn’t flustered) to 1980’s Mariel boatlift, best remembered as the inspiration for Brian De Palma’s Scarface. It is, incidentally, impossible to imagine American cinema of the past 50 years without Fidel’s inadvertent contributions: besides Scarface, think Woody Allen’s Bananas, Steven Soderbergh’s Che, or, of course, The Godfather Part II. Will that be his most enduring legacy, at least in the United States?

The Soviet Union went belly-up in 1991, which turned Castro into a relic for real. (It was around then I started calling him “Robinson Khruschev,” a joke I’m still ridiculously fond of.) When the only American leftist who still thinks you’re hot shit is Oliver Stone, it’s safe to say the jig is up. Not until 2006 did he cede power to Raul Castro, who must have been pretty sick by then of Fidel quipping, “He ain’t El Jefe—he’s my brother.”

The dictator did outlast 10 U.S. presidents, and could have claimed 11 if he’d made it to the end of Obama’s term. That’s an undeniable feat, considering most of them wanted him gone. For that matter, the only world figure who’s outlasted him is Queen Elizabeth II, his near-exact contemporary. I bet she’s feeling awfully smug around now, but a Cuban version of The Crown wouldn’t suit Castro’s career at all. For over half a century, he was more like Wile E. Coyote and the Roadrunner rolled into one.