The Most Bizarre Assassination Plots That Almost Worked

Assassinations have always played a role in shaping history, whether it’s the dramatic end of Julius Caesar or the tragic assassination of JFK. But not all assassination plots succeed. Some miss the mark in ways so bizarre they sound more like bad movie scripts than real life. These aren’t the meticulously executed plans we read about in history books. These are the weird, messy, and often ridiculous attempts that failed—but almost worked. Let’s dive into some of the most surreal and stranger-than-fiction plots that could’ve changed the course of history. Here are the bizarre assassination plots that almost worked.

Fidel Castro

If assassination attempts were an Olympic sport, Fidel Castro would be a gold medalist—for surviving. The Cuban leader was targeted by the CIA and other enemies so many times (some say over 600) that it’s almost laughable. And while some of these plots were straightforward, others were downright absurd.

Take the exploding cigar, for instance. Castro was known for his love of fine Cuban cigars, and someone at the CIA thought, “What if we made one blow up in his face?” It was the kind of plan that sounds like it belongs in a cartoon. Another equally ridiculous scheme involved a poisoned milkshake. CIA agents even created a capsule filled with a deadly toxin, but the would-be assassin fumbled it. The capsule broke before it could make its way into Castro’s drink.

And then there was the scuba diving fiasco. Castro loved diving, so the plan was to gift him a wetsuit dusted with deadly fungal spores or infect him with tuberculosis. To top it off, they even considered planting a booby-trapped seashell in one of his favorite diving spots. It would’ve been brightly colored and filled with explosives, hoping Castro would be too curious to resist picking it up.

The most bizarre plot, though, might be the beard sabotage. The CIA theorized that Castro’s iconic beard was part of his power. So, they developed a plan to sprinkle thallium salts in his shoes or cigars to make his hair fall out. Because, obviously, a beardless Castro would lose the respect of the Cuban people, right?

Remarkably, Castro outlived all these attempts, dying of old age in 2016. He even joked about it later, saying, “If surviving assassination attempts was an Olympic event, I’d win gold.”

Franz Ferdinand

We’ve all taken a wrong turn, but most of us haven’t triggered a world war because of it. Franz Ferdinand, the heir to the Austro-Hungarian throne, wasn’t so lucky. His assassination in 1914 set off a chain reaction that led to World War I, but what’s often overlooked is just how chaotic the whole thing was.

On the day of the assassination, the Black Hand, a group of Bosnian Serb nationalists, had planned to kill the Archduke during his motorcade. One of the conspirators threw a grenade, but it bounced off Franz Ferdinand’s car and exploded underneath another vehicle, injuring several people. The Archduke and his wife, Sophie, were unharmed, but the plotters weren’t done yet.

After the failed attempt, Franz Ferdinand insisted on visiting the hospital to see the injured. However, his driver wasn’t familiar with Sarajevo’s streets and made a wrong turn. By sheer coincidence, this wrong turn brought the Archduke’s car right in front of Gavrilo Princip, one of the remaining conspirators. Princip seized the moment, pulled out a pistol, and shot both Franz Ferdinand and Sophie.

It’s almost unbelievable how a failed grenade attack and a wrong turn led to the deaths of millions. If just one detail had been different, who knows how history might’ve played out?

Georgi Markov

Imagine waiting for a bus on a regular day, only to feel a sharp sting on your leg—and then dying a few days later. That’s what happened to Georgi Markov, a Bulgarian dissident living in London in 1978.

Markov was a vocal critic of Bulgaria’s communist regime, which didn’t sit well with those in power. On the morning of September 7, Markov was standing at a bus stop when a man brushed past him, apologizing as he fumbled with an umbrella. At first, Markov thought nothing of it. But by the end of the day, he was feverish and in intense pain.

Doctors later found a tiny pellet embedded in his leg. It was loaded with ricin, a deadly poison. The umbrella, it turned out, was a high-tech assassination weapon developed by the KGB. It could inject a small amount of poison without anyone noticing.

Markov’s death became one of the most chilling reminders of Cold War espionage. It also fueled countless conspiracy theories about the lengths governments would go to silence dissent.

Adolf Hitler

Adolf Hitler was the target of numerous assassination attempts, but none were as dramatic as the July 20 Plot in 1944. German officer Claus von Stauffenberg led the effort, hoping to end Hitler’s reign and negotiate peace to save Germany from further destruction.

The plan seemed simple enough: Stauffenberg would plant a bomb in a briefcase and place it under the table during a meeting at Hitler’s headquarters, the Wolf’s Lair. The bomb went off, killing four people and injuring many others. But Hitler survived, thanks to pure luck.

Someone had moved the briefcase slightly, placing it behind a thick wooden table leg. The table absorbed much of the blast, leaving Hitler with only minor injuries. The failed attempt led to brutal consequences, with thousands of people arrested, tortured, and executed.

Despite its failure, the July 20 Plot remains one of the most famous resistance efforts against Hitler, showing that even in the darkest times, there were those willing to risk everything for a chance at change.