The Strangest Political Assassination Attempts in History

When it comes to history, political assassinations are often grim, tragic, and world-changing. But every so often, you stumble across one so bizarre that it feels like something out of a dark comedy. So, let’s take a look at some of the weirdest and most unbelievable assassination attempts that somehow actually happened.

Fidel Castro and the Exploding Cigar

You can’t talk about strange assassination attempts without mentioning the CIA’s decades-long obsession with killing Fidel Castro. Between the 1960s and 1980s, the U.S. intelligence community basically treated Castro’s survival as a personal insult. They tried everything — and I mean everything.

There were poisoned wetsuits, booby-trapped seashells, hallucinogenic sprays meant to make him sound insane during speeches, and, most famously, exploding cigars. The logic was simple: Castro loved cigars. So why not make one blow up in his face?

The CIA reportedly developed cigars packed with high explosives and even others laced with deadly toxins. Fortunately (or unfortunately, depending on your point of view), none of these plans worked. Castro somehow outlived nine U.S. presidents and died peacefully in his 90s.

The Confused Fox

In 1800, Napoleon Bonaparte was attending a performance at the Paris Opera when a group of royalist conspirators decided to blow him up. They built a cart packed with gunpowder and metal shrapnel, which they called an “infernal machine.” Their plan was to detonate it as Napoleon’s carriage passed. Simple enough.

Except the assassins got confused about which carriage was his. They ended up blowing up the wrong one — killing innocent bystanders while Napoleon drove on, unharmed and probably irritated about the traffic. The blast shook Paris, destroyed buildings, and killed several people — but the intended target simply arrived at the opera, dusted himself off, and enjoyed the show.

The “Curse” of the Orange Box

Queen Victoria was one of the most targeted monarchs in history. She survived eight separate assassination attempts — and some of them were incredibly strange.

In 1840, just months after her marriage to Prince Albert, a man named Edward Oxford decided he wanted to become famous. His brilliant plan? Shoot the queen in broad daylight as she rode in her carriage through London. He fired two pistols at her — and missed both times.

When police arrested him, they found his pockets stuffed not with bullets or extra weapons, but with a notebook full of made-up stories about an imaginary secret society he claimed to lead. Turns out, Oxford wasn’t part of some political plot — he was just delusional and wanted attention. He spent the rest of his life in an asylum, later moving to Australia and becoming a bartender.

The Time Someone Tried to Kill Hitler… With Cake

There were over 40 documented attempts to assassinate Adolf Hitler — and a surprising number of them were just plain weird. One of the lesser-known ones involved a group of German officers who decided to hide a bomb inside a box of brandy and cake. It was supposed to explode midair on Hitler’s plane as he returned from a meeting.

The plan almost worked — except the detonator froze in the unheated luggage compartment, and the bomb never went off. Hitler landed safely, completely unaware that dessert had nearly ended his dictatorship. Later, another famous attempt (the July 20 plot) also failed because the bomb’s placement under a heavy wooden table absorbed much of the blast.

The Knife, the Notebook, and the Mayor of Chicago

In 1933, a man named Giuseppe Zangara decided he hated politicians — all of them, apparently. He went to Miami, Florida, where President-elect Franklin D. Roosevelt was giving a speech. Zangara stood on a chair, pulled out a pistol, and started shooting wildly toward the podium.

He missed Roosevelt entirely but managed to hit Chicago Mayor Anton Cermak, who was standing nearby. Cermak later died from his wounds, reportedly telling FDR: “I’m glad it was me instead of you.” Zangara’s only explanation for the attack? He said his stomach hurt all the time and blamed rich people for it. That’s… not exactly a manifesto.

The Letter That Was Literally Too Hot to Handle

In 2001, an attempt was made to assassinate the president of Taiwan, Chen Shui-bian, with a letter bomb hidden inside a greeting card. The card contained a small amount of explosive material and was designed to detonate when opened. Unfortunately for the sender, the bomb went off early, injuring a postal worker before it ever reached its target.

The would-be assassin was later caught and confessed that he simply didn’t like the president’s policies. No shadowy spy agencies. No elaborate plot. Just a guy with bad timing and even worse engineering.

The “Umbrella Murder”

Perhaps the strangest assassination that actually worked took place in 1978, in the middle of London. Bulgarian dissident Georgi Markov was waiting for a bus when he felt a sharp sting in his leg. He turned around and saw a man picking up an umbrella before quickly walking away.

Three days later, Markov was dead. An autopsy revealed a tiny metal pellet inside his leg, which was filled with the deadly poison ricin. Investigators concluded that the assassin had used a modified umbrella to inject the toxin. It was Cold War spycraft at its most surreal, and it became one of the most infamous murders of the 20th century.

The Guy Who Tried to Kill Andrew Jackson

In 1835, President Andrew Jackson was attending a funeral when a man named Richard Lawrence decided to make history — badly. Lawrence pulled out a pistol, aimed at the president… and it misfired. He pulled out a second pistol… and that one misfired too.

Before he could try again, Jackson, 67 years old at the time, beat him nearly unconscious with his cane. Both guns were later tested and found to be in perfect working order. Historians still can’t explain why they both failed. Divine intervention? Bad luck? Either way, the president walked away with his ego — and his cane — intact.