The Most Incompetent Bucket List Ever Written

Picture this: You're a top-secret CIA operative during the height of the Cold War. Your mission? Kill one man. Simple enough, right?

Wrong. So, so wrong.

Fidel Castro managed to survive 638 assassination attempts—yes, I counted, well, the article counted, but still—over the course of his reign. And the methods the CIA dreamed up? They're so ridiculous that if someone pitched them as a movie plot, you'd laugh them out of the studio.

Let me walk you through some of the highlights. (Or lowlights, depending on your perspective.)

It All Started With a Bad Day at the Bay of Pigs

Here's the backstory: In 1961, the CIA backed an invasion of Cuba at the Bay of Pigs that went about as well as you'd expect a plan to go when you've got amateur hour running the show. Castro's forces crushed the invaders in less than 72 hours.

So there was Castro, lighting up a celebratory cigar while American officials were left humiliated and scrambling. That's when Operation Mongoose was born—a codename that sounds way cooler than the absolute disaster it turned out to be.

Where Do I Even Start?

The CIA threw everything at the wall to see what would stick. Spoiler: nothing did.

The poisoned cigars were a personal favorite of mine. They actually got botulinum toxin on some cigars and everything. But somehow—somehow—they never made it to Castro's lips. Lost in transit? Intercepted? My money's on cosmic intervention.

The exploding seashell was ambitious. The plan was to plant an explosive inside a seashell at Castro's favorite fishing spot. The tides would reveal it, and kaboom. Except—and this is my favorite part—they couldn't find a shell big enough to hide the explosives. I'm not making this up.

And then there was the fungal wetsuit. The CIA actually considered coating Castro's diving suit with fungus that would cause hideous skin growths. Imagine explaining that one in a debriefing. "Sir, our mission status is... creative."

The Mafia Joins the Party

Here's where it gets really wild. The CIA actually partnered with the mob to take down Castro.

They recruited Johnny Roselli (whose nickname was literally "Handsome Johnny"—this feels like a bad joke already) to reach out to top mobsters Sam Giancana and Santo Trafficante. These were guys the FBI wanted badly, and suddenly Uncle Sam was working with them?

The mob had ideas too. They suggested throwing a grenade at Castro during a baseball game. They pitched poisoning his milkshake at a Havana hotel. The poison capsule froze in the freezer before it could be used.

I wish I were making this up.

The Biological Warfare Angle

This is where things get genuinely uncomfortable.

The CIA experimented with infected ticks intended to spread disease in Cuba. There's evidence suggesting these experiments may have backfired spectacularly, possibly contributing to Lyme disease outbreaks in the United States.

They also thought about slipping tuberculosis bacteria into his breathing apparatus. A scorned ex-lover was recruited to slip poison into his drink, but apparently even she couldn't bring herself to do it.

At this point, you have to wonder if Castro had some kind of supernatural luck, or if the universe was just having a field day with the CIA.

What Did They Actually Accomplish?

Here's the punchline: Not much.

Operation Mongoose managed to establish a trade embargo (one that still exists today, by the way), some sabotage operations, and absolutely zero successful assassinations.

Castro lived until 2016, dying of natural causes at age 90. He outlasted nine U.S. presidents. He saw the Bay of Pigs, the Missile Crisis, the Cold War, and the fall of the Soviet Union. Through it all, those cigars kept burning, and the CIA kept failing.

My Take

Honestly? This whole story is equal parts terrifying and hilarious.

It's terrifying because it shows just how far American intelligence was willing to go during the Cold War. Biological warfare against civilians? Working with organized crime? These aren't exactly ethical checkpoints on the way to success.

But it's also hilarious because the plans were so stupid. A seashell that was too small. A milkshake that froze. Poisoned cigars that got lost. You really have to question the quality of CIA brainstorming sessions in the early '60s.

What strikes me most is the sheer persistence. 638 attempts! You'd think after the 50th failure, someone would say, "Maybe we should try diplomacy?" But no. It was always, "What about... more poison?"

Castro wasn't a good man, by most accounts. But you have to admit, the man had an incredible run of luck.

Sometimes I wonder what happened to all those failed plots in CIA archives. Are there still boxes of ruined seashells in some basement? Probably. And honestly? I hope they're never opened.

Source: Popular Mechanics