From Castro to Cheney: history’s most insane assassination plots

Last year was a weird one for assassinations plots.

We learned that former Vice President Dick Cheney was so worried about the security of his artificial heart that he asked his doctors to deactivate its wireless device, lest hacker assassins use it to deactivate him.

Then a Mexican drug lord was killed at a children's party in Cabo San Lucas by a team of assassins dressed as clowns.

These sound like crazy assassination plots, right? Not especially.

Target: Fidel Castro
Method: Take your pick

Fidel Castro in Algieria, 1973. (Stig Nilsson/Getty Images)

Any conversation about crazy assassinations plots needs to start with Fidel Castro, who was likely the target of more assassinations plots and attempts than any other human in history. Some estimates put the number as high as 600. Like all the plots on this list, those against Castro blurred the line between "crazy" and "crazy like a fox." 

The CIA was the preeminent creative force when it came to killing Castro. When I try to imagine how these plots were hatched, I picture the writers' room at Saturday Night Live. But instead of joke ideas, these bespectacled nerds were tossing around ideas for how to murder world leaders. Most of their ideas, of course, turned out to be jokes. 

The plots against Castro that emerged from the CIA.'s assassins' room can be broken down into two main categories: Poisoned Things and Exploding Things. 

1) Poisoned Things: A wetsuit (Castro liked scuba diving); a poison-filled syringe disguised as a ballpoint pen; a cigar laced with botulin; a handkerchief covered in bacteria; and a milkshake.

2) Exploding Things: Most famously, a cigar. Less famously, a conch shell on the sea floor.

None of these worked. In his prime, Castro was the Mike Tyson of assassination targets. His defense was impregnable. Castro nows spends his days dodging nature's assassin: age. 

Target: Agrippina the Younger
Method: Mechanical ceiling. Self-sinking boat.

Agrippina and her son, Nero, depicted on a Roman coin. (Wikimedia Commons)

As Castro's life attests, the CIA owned the insane assassination plot during the Cold War. But there were plenty of crazy plots of yesteryear that would make even the CIA tip its cap.

Nero, the Roman Emperor between 54 and 68 AD, came up with two such schemes while trying to off his mother, Agrippina. Even though Nero was Emperor, Agrippina still held a great deal of power. Nero, whose name became synonymous with brutality, was not one for power sharing. Mom had to go.

Accounts of the plots vary, like most accounts of things that happened forever ago. According to some contemporary chroniclers, Nero had a mechanical ceiling above his mother's bed that, when activated, would crush her to death. That didn't work, so he put his full effort into drowning her at sea. Some claim that he instructed captains of other vessels to ram Agrippina’s ship until it sank. Others describe a collapsible boat, specially built to sink itself with her on board. Either way the ship plan didn’t come off as hoped, so Nero went with a tactic that was already old-fashioned in 58 AD: having assassins murder her and frame it as a suicide.

Quite the son.

Target: Jörg Jenatsch
Method: Axe, wielded by a man in a bear costume

Jörg Jenatsch, Rätisches Museum. (Wikimedia Commons)

Fast forward to 17th century Switzerland. There, we encounter Jörg Jenatsch, a political leader and fairly unlikeable dude. Something of an assassin himself, he participated in the axe murder of a political rival in 1621. That is to say, Jörg had it coming.

It took almost two decades for Jörg's comeuppance, and when it came, it came in style. The year was 1639 and the season was Carnival. Everyone was in costume as something crazy, so it was easy to overlook a strike team of assassins dressed to party. Still, Jörg should have kept a better eye on the man decked out head-to-toe in a bear costume. That bear was carrying an axe, and that axe would end up buried in Jörg.

The assassins were never identified. It's suspected, though, that the axe-wielding bear was the son of the same political rival that Jörg had helped axe so many years earlier.

Target: Patrice Lumumba
Method: Toothpaste

Patrice Lumumba in Brussels, January 1960. (Getty Images)

Fast forward again to the Cold War and the case of Patrice Lumumba.

Lumumba was a key figure in the Congolese independence movement and the first democratically elected Prime Minister of the Democratic Republic of Congo. He was elected in June 1960. Three months later, he was deposed in a coup and executed by firing squad.

There are suspicions that the CIA, Britain's MI6, and the Belgian government each played a role in the coup. The ostensible American interest was that Lumumba was a pan-Africanist and seemed too friendly with the Soviets. That wasn't a surprise, since an anticolonialist would obviously support the struggles of his anticolonial neighbors, and since the USSR had been more supportive of anticolonialist movements than the United States had been. Belgium, for their part, considered Lumumba a threat to their stake in Katanga, a mineral-rich province that, with Belgian backing, sought to break from the Democratic Republic of Congo. Either way, Lumumba ended up dead. The precise role of the CIA, MI6, and the Belgian government remains undisclosed.

What is known for sure is that the CIA had devised an assassination plan against Lumumba that was never carried out.

Larry Devlin, the CIA’s Congo station chief at the time, recalled the moment when he first became aware of the plot. It was the moment he was handed poison toothpaste and told to get it into Lumumba's mouth. Devlin was shocked. He hid the toothpaste in his office safe and then threw it in the Congo River.

Target: Admiral Luis Carrero Blanco
Method: Explosives packed into a homemade tunnel

Policemen search among the wreckage caused by a bomb attack on Dec. 20, 1973 in Madrid, Spain (GettyImages)

Next up: an assassination plot in fascist Spain. The year was 1973. Luis Carrero Blanco was the Prime Minister. Blanco was the successor to fascist dictator Francisco Franco, which means he came into office with plenty of enemies, including the ETA (Euskadi Ta Askatasuna), a Basque separatist group.

While Catalan separatists were cheering on Johan Cruyff, the newly arrived Dutch star at F.C. Barcelona, the ETA was planning to kill Prime Minister Blanco.

The plot was code-named Operación Ogro. ETA operatives rented an apartment along the driving route that Blanco used to attend mass, claiming to be sculpture students to keep the landlord’s suspicions at bay. All they were sculpting, though, was a tunnel from their apartment outward, across the street that Blanco would be crossing in a Dodge Dart en route to his weekly holy obligation. The faux-sculptors packed the tunnel with 80 kilograms of explosives, and on Dec. 20, 1973, three operatives dressed as electricians, remotely detonated the explosives as Blanco passed by. The prime minister died from his injuries.

Target: Georgi Markov
Method: Ricin pellet, shot from an umbrella

People attend a commemoration service marking 35 years since the death of Georgi Markov, a bulgarian disident killed in London in 1978. (Nikolay Doychinov/Getty Images)

Here's a ricin murder conspiracy decades before Breaking Bad.

Georgi Markov was a Bulgarian dissident and communist defector who settled in London and worked for the BBC World Service in the 1970s. On Sept. 11, 1978, he left work and headed home. He was standing at a bus stop when he felt a sharp sting in his thigh. When he turned around, he saw a man picking up an umbrella and apologizing.

Four days later he was dead.

The autopsy discovered a pellet containing .2 milligrams of ricin. Investigators never found the assassin or uncovered the plot. It's widely assumed to have been orchestrated by the KGB.

Target: Khaled Meshaal
Method: Poison injected into the left ear

Hamas leader in exile Khaled Meshaal waves goodbye upon his departure from the Gaza Strip on Dec. 10, 2012 in Rafah, on the border with Egypt. (Said Khatib/Getty Images)

Khaled Meshaal is a Palestinian leader of Hamas’ political bureau. The year was 1997. Benjamin Netanyahu, now prime minister of Israel, ordered an assassination on Meshaal. It was a major debacle.

Five agents from Mossad, Israel's version of the CIA, traveled to Amman, Jordan in pursuit of Meshaal. They posed as Canadian tourists and tried to kill Meshaal in broad daylight on the street by injecting poison into his ear.

The poison was supposed to induce immediate paralysis and imminent death. It didn't, and Jordanian security forces arrested two Mossad agents and forced three others into hiding.

To secure their release, Netanyahu freed dozens of prisoners from Israeli jails, including nine Jordanians, 61 Palestinians, and Sheikh Ahmed Yassin, the “spiritual leader” of Hamas.

And he handed over the poison antidote.

Things, you could say, did not go as planned.

Target: Osama Bin Laden
Method: Vaccination program

An Afghan health worker (R) administers a polio vaccine to a child during the first day of a vaccination campaign on the outskirts of Jalalabad, Nangarhar province on July 1, 2013. (Noorullah Shirzada/Getty Images)

One of the weirdest assassination plots is also one of the most famous.

If you've watched Zero Dark Thirty, or read a newspaper in the last couple of years, you know the going story of how Osama bin Laden was killed: a team of Navy Seals assaulted his compound in Abbottabad, Pakistan and shot him in the head.

But the assassination itself shouldn't distract you from the plot that preceded it.

When the CIA developed a sense of where Osama bin Laden was hiding out, they knew they needed proof. His DNA would be good proof, right? But how to get it?

They recruited a Pakistani doctor, Shakil Afridi, to run a door-to-door polio vaccination campaign in Abbottabad, with the hope of getting close enough to bin Laden to extract a DNA sample.

The plan didn't work, but it has had huge effects in the region. Health workers now have a harder time than ever administering to patients in Pakistan and Afghanistan. If a vaccination campaign had once been a cover for espionage and assassination, so why not again? Vaccination workers have been murdered, and this summer, the Taliban announced a ban on vaccinations in Pakistan's tribal regions. It will remain in effect until US drone strikes end.

So there you have it. The lesson here is a depressing one: that people and nations seem to do their most creative thinking when trying to murder someone.