There Were 638 Attempts to Assassinate Fidel Castro – Here Are Some of the Weirdest

This year Cuba lost one of its country’s most iconic and polarizing figures, Fidel Castro. The revolutionary governed the country as Prime Minister and then President for an accumulative total of 49 years! That Castro died from natural causes is ironic, considering the number of attempts on his life over the years. We’re going to look at a few of the weirdest right now.

Death By Lover

It’s the oldest story in the book, and like something right out of a hard-boiled detective novel. We’re talking, of course, about the femme fatale approach. This was one of the cleverer attempts by the CIA to try to dispose of Castro. They made contact with his lover and mistress Maria Lopez. The idea was for her to poison Castro as he slept, with poisoned pills she hid in a jar of cold cream. This backfired when she was unable to do it. But it seems wily old Fidel knew what she’d been up to, and even offered her his pistol to shoot him. She’s alleged to have said “I just can’t, Fidel’, and the two then made love. He obviously had some sort of crazy super power that made her unable to do it!


Exploding Cigars

Another one that seems pretty logical, as Castro was a heavy smoker and big cigar lover. The idea here was to place some explosives inside a cigar and hand it to Castro at a United Nations meeting. This was one of many assassination attempts made using cigars. This was apparently the brainchild of a New York City cop and seems like a pretty sound idea in theory. The problem, of course, is that it would only work if the cigar found its way to Castro. Now, apparently, this fell through because the agent who was supposed to get the cigar to Castro got cold feet. Not exactly what you want from someone who is meant to be an assassin is it?!


Diseased Scuba Gear

Okay, now we’re really getting creative! Scuba gear infected with a deadly disease seems a pretty ingenious way of killing someone. And Castro did love scuba diving, so it seemed like the go-to idea. Yes, it made sense, but it’s still a really weird idea, and probably was one of those they came up with having tried everything else! The guy tasked with presenting Castro with this diseased suit was James Donovan. Incidentally, he’s the guy portrayed by Tom Hanks in the movie Bridge of Spies. Anyway, Donovan never actually presented the famed socialist with the TB-infused suit. Instead, Castro was given a disease-free one, but it’s unclear if this was intentional or by accident.


Exploding Conch Shell

The CIA must have been getting really desperate now because this has got to be the weirdest of the bunch. Like something out of a James Bond movie, the US government tried to set some explosives in a shell and place it in Castro’s favorite diving spot. You can just imagine Roger Moore’s 007 swimming out in his scuba gear under the dead of night and planting the explosives. However, whoever came up with the plan obviously hadn’t thought through the logistics. Apparently, CIA head Desmond Fitzgerald, who led the anti-Castro Task Force, tasked his assistant with the ins and outs of this plot. Presumably, the assistant gave it a thumbs down because the plot never ended up transpiring.


LSD Cigars

It wasn’t just assassination attempts that Castro had to contend with, there were also character assassination attempts. Presumably, once the CIA found he was harder to kill than Rasputin, they decided to go for a different approach. There were extensive plans in place to try to reduce Castro’s credibility. And one of the more loopy ones was to spike the Cuban leader with cigars laced with LSD. The thinking behind this was that it would send Castro a bit crazy and make him lose credibility during a radio broadcast. We have to say, this is one of the wackier ideas we’ve heard of, and unsurprisingly it never happened. There was also a discussion in the CIA’s Technical Services Division about spraying the studio with LSD as well.


If you thought the LSD plot was a little bit bonkers wait until you get a load of this one! The good old Technical Services Division had obviously been reading the story of Samson and Delilah when they came up with this. The idea was to dust Castor’s shoes with thallium salts. These are known to cause hair loss, and it was hoped that his beard would fall out. The thinking behind this is that the people would look at Castro differently once they saw he had no beard. Unfortunately, the powers that be didn’t seem to deduce that his power didn’t come from his beard! Everything was set in motion, and it was decided that this would happen when Castro left his shoes outside his hotel room to be dusted on a trip abroad. The plot was foiled when the Cuban revolutionary canceled the trip, and it was back to the drawing board.


Poisoned Chocolate Milkshake!

It sounds dumb, but this is actually thought to be one of the closest attempt to actually dispose of Fidel Castro. There are a few different versions of this story, one being a Mafia plot involving ice cream. But the milkshake is the most well known, and they essentially go in the same direction. So the ploy was simple, Tony Varona was given a vial of poison, and he had to slip it to a worker at Castro’s favorite Havana ice cream shop. Then the worker was tasked with depositing the poison into his milkshake and hey presto! But the attempt was thwarted when the vial became stuck in the freezer, and an attempt to remove it resulted in it cracking and the poison spelling. That’s the problem with involving too many different people in the process guys!


The Mafia

So we know that the Mafia was directly involved in the milkshake poisoning attempt. But, there is no doubt the Mafia would have concocted other plots as well. It’s well documented that they were no lovers of Castro. In fact, their hatred of him was so extreme they even waived the fee they would normally charge for assassinations. The CIA even were thought to have teamed up with the Mafia to take him out, and still, they couldn’t kill him! It was the early 1960s, and the mob had it in for Castro because he was shutting down their casinos and affecting their financial profits. This led directly to milkshake-gate. But, there’s no doubt the mob would also have made other attempts over the years to take out the Cuban leader.


Hypodermic Pen

Now this one really is a plot right out of a James Bond movie. Obviously inspired by Britain’s suave secret agent, the CIA concocted a cunning plan. They managed to rope in a double agent to help them in their attempt. The plan was that a ballpoint pen would be rigged with a hypodermic needle, and used to inject Castro with some form of a deadly disease. The insider was a high-ranking Cuban official, known in CIA papers only as AMLASH. He was later discovered to be Cuban revolutionary Rolando Cubela. Allegedly he asked for a collection of high-powered rifles with scopes. Not wanting to be taken for fools the CIA wisely refused and instead offered up the hypodermic pen as an idea. AMLASH apparently derided the idea and wanted something more sophisticated. So that was that idea out the window!


Exploding Baseballs

We know that baseball can be an explosive game at times, but not literally! Consider for a moment the idea of using our national sport as a way of taking out the enemy. Well, it’s something that no one would see coming, but that’s mainly due to the safety aspect. And so it came to pass the idea to blow up Castro up with baseball grenades during a game. Naturally, you can imagine the health and safety gurus would have had a field day. It’s no surprise that the plan was abandoned over fears that it would be unsafe for players and fans alike. Well, duh. Can you imagine anyone coming up with such a reckless and dangerous idea today?!


Panama Summit Explosion

Sometimes, if you want something done, you have to go about it in the old-fashioned way. And when it comes to assassination attempts that sometimes means blowing people up! So, you can understand why the CIA at some point decided they needed to go back to basics and blow Fidel sky high! The Cuban leader was giving a speech in Panama, and there was a plan to possibly put explosives under the podium he was going to use. Again, this was another plan that was aborted due to long-standing safety concerns over the threat to bystanders. The CIA really didn’t have much luck did they? And they didn’t really seem to think things through and consider their practicality.


Poisoned Cigar

It’s those pesky cigars again! Not content with trying to blow Castro up or dose him with LSD using his prized cigars, there was also a plan to poison his cigars too. This is arguably the most famous attempt on his life and took place in the 1960s. An official was given a box of Castro’s favorite cigars and instructed to lace them with a poison so strong he would die just from placing one in his mouth. This was perhaps the most foolproof plan as everyone knew how much Fidel loved a stogie. It’s unclear whether the cigars were passed to Castro, but it’s thought the agent tasked with the responsibility got cold feet.


Consulting a Novelist!

Believe it or not, the US government actually consulted with famed novelist Ian Fleming. The story goes that, during a dinner in 1960, President Kennedy asked for Ian Fleming’s advice. Kennedy was notably a huge James Bond fan and bent the author’s ear for suggestions. It’s unclear how serious Kennedy was or whether he was just, to coin a phrase, chewing the fat with the famed novelist. With typically British wit, the author suggested that Kennedy spread rumors that the Cuban leader was impotent. Fleming may have said this with tongue firmly in cheek, but the idea of humiliating and discrediting Castro is something the US government explored.


Deadly Handkerchief

Poisoning Castro seemed to be the avenue of choice for the CIA. And they attempted yet another poisoning, only this time it was done using a handkerchief. They were seemingly obsessed with showering him with disease and bacteria. An attempt was made to give him a germ covered handkerchief that would poison him. It obviously didn’t work, but it’s unclear as to why. It could be that the logistics of getting a bacteria-ridden hankie to Castro was probably too difficult. Who would take a hankie from someone they didn’t know? Especially when you know, people are targeting your life. Sort it out CIA!



You wonder why they didn’t try a sniper before! Indeed, apparently, there was an assassination attempt when a sniper tried to take the Cuban leader out at the University of Havanas. However, the assailant was caught by security before he was able to carry out the attempt. It seemed Castro was pretty fearless and when asked whether he wore a bulletproof vest he replied that he wore a ‘moral vest.’ In fact, The Beard seemed to wear his assassination attempts as a badge of honor. He is quoted as saying that if the Olympic Games had a sport for surviving assassination attempts “I would want the gold medal.” And, looking at how many different attempts there were it’s hard to argue with him.


Hemingway Museum

It might surprise you to hear that Castro was a huge fan of writer Ernest Hemingway. Perhaps not so surprising, given that the author is one of the greatest writers in history. But there were long-standing rumors the two were friends. This may have been unsubstantiated, but Castro remained a fan. How does this link? Well, another assassination attempt on Castro took place when he visited Hemingway’s museum in Cuba. There was an attempt made to blow him up, though it’s unknown why this didn’t end up happening. It seems as though God himself may have been on the side of the polarizing revolutionary.



If you thought the would-be Castro assassins were all cloak and dagger you’d be wrong. Cuban exile Antonio Veciana actually attempted to kill Castro a few times, and had one attempt that involved a bazooka! It’s often said that sometimes a blunt instrument is the best way to go. And this is a good example of that; though imagine the damage a bazooka could do. We’re pretty sure the CIA weren’t involved in this, at least not directly. It would have been too messy for them to have considered as a viable attempt. But, after the failed attempt to dispose of Castro at the Bay of Pigs, Veciana directed as assassination attempt from a Havana apartment. Unfortunately for him, and the USA, the attempt was unsuccessful.