Shockingly, the plan sort of ... worked? The two men got the poison in his ear, but Mashal's bodyguards saw it and chased them down. The remaining agents fled to the Israeli embassy, which was quickly surrounded by troops. It turned out that squirting poison into a political leader's ear and running away was not as subtle as they'd hoped. The five would-be assassins tried to blend in by falling back on their cover as Canadian tourists, their hopes hanging entirely on people believing that Canadians were so stupid that they would seek shelter in a completely different country's embassy.

And boy howdy, these men were especially not Canadian. They didn't know basic facts about the country, couldn't sing its national anthem, and each wrote "f**k YOU THIS IS CRAZY" next to pictures of milk in bags. They didn't even know about the Toronto Blue Jays, who had recently won back-to-back World Series. They knew so little about Canada that they might have been trying to invent a fake country and accidentally landed on three syllables that happened to be a real one.

The king of Jordan, dying of cancer at the time, was not amused in the slightest by these -- to be fair, highly amusing -- antics, and put Israel through the wringer. Not only did they have to provide the antidote to cure Mashal, but they were also forced to free a bunch of political prisoners. They failed so hard at assassination that they wound up with a net positive for the living. It was an absolutely humiliating loss, and Benjamin Netanyahu had to fly to Jordan to publicly apologize to Crown Prince Hassan, swearing it would never be repeated. Hassan later said it was one of the most bizarre things he had ever experienced. We're inclined to agree.

Trujillo was furious, and started a nonsensical anti-Church campaign. He issued 1,000 fake invitations to a reception hosted by Archbishop Lino Zanini, ensuring the place was swamped by a massive crowd. Then he had prostitutes barge in to dance to obscene songs while his men dropped stink bombs in the place. When the old Smelly Whore Gambit inexplicably failed to bring the entire Church down, Trujillo unveiled his most daring plan yet: the assassination of the pope himself.

Fortunately, as you may already have gathered, Trujillo was not totally tethered to reality. Instead of "some guy with a gun," he summoned a local one-armed spell-caster who could supposedly curse people with the evil eye. The man was informed that he was being sent to Rome as "Secretary of the First Class in the Embassy at the Vatican," and his sole job would be to use his mystical powers to kill Pope John XXIII, whom Trujillo had nicknamed "Juan Pendejo."

Wiki CommonsHis next choice was "The Poop"

So did the vague plan to murder someone with bad luck work? Well, the one-armed curse-monger went to Rome, and Dominican newspapers even published a photo of the new "secretary" meeting the pope. But the pope's good magic must have cancelled out Trujillo's evil magic so hard that it reflected back, because Trujillo himself was murdered within the year. So, young warlocks, remember: If you're going to go magic-to-magic with God's main guy, you best bring both hands.

On another occasion, the CIA smuggled more dissolving poison pills to Castro's mistress, Marita Lopez, but she brilliantly decided to hide them in her cold cream, where they, y'know ... dissolved. Lopez did not then hatch a plan to get Fidel to eat the cold cream; she dumped the whole sticky mess down the toilet. The Mafia then smuggled six more poison pills to Castro's secretary, but he panicked and went into hiding (he eventually showed up again as a toll booth operator in Miami).

You're probably taking a very comforting lesson from this: Most people aren't super comfortable with (or competent at) murder. The CIA never got that one, though. They continued trying to turn everyone Castro ever knew into an assassin. They bribed one of his bodyguards to do it, and he became so visibly nervous that people thought he was having a heart attack. He ultimately broke down and sobbed out a confession.

Attempts to use an unwitting patsy didn't go any better. One plan had U.S. negotiator James Donovan (of Bridge Of Spies fame) giving Castro a poisoned wetsuit as a gift. Yes, a poisoned wetsuit. And you won't believe the monkey wrench that derailed that plan: It turns out Donovan had, through sheer bad luck, already given Castro a non-poisoned wetsuit as a gift. Politics might seem insane right now, but for decades, we lived in a world in which the United States government performed wacky slapstick comedy for an audience solely of Castro.

One early plan involved giving Nasser a bomb disguised as an electric razor, which was designed to activate when it was pressed up against stubble (MI6 presumably had a mole standing by to make a quip about a "close shave"). Another plot saw an agent spending hours carefully heating and cutting chocolates open to put poison inside. Someone almost certainly suggested the line "Now this is what I call death by chocolate," before they abandoned the plan because they were worried Nasser might share his candy. No, that's really the reason. It's a problem they wouldn't have had to worry about with Nasser's predecessor, King Farouk, shown here in swimming trunks size Pickle Barrel.

A plan to bribe one of Nasser's doctors went wrong when the English bagman got confused and accidentally left a parcel containing 20,000 pounds for the wrong Egyptian. A special cigarette package that fired poisonous darts was successfully tested on a sheep, but never used, presumably because MI6 realized that shooting a guy with a cigarette dart is basically as obvious but less deadly than shooting him with a gun.

Finally, MI6 thought, "Screw it. Nerve gas?" They wanted to try pumping lethal gas into the vents of Nasser's palace to kill everyone inside. Luckily, that plan was nixed by Eden, who wasn't enthusiastic about "war crimes business." Instead, Eden took a bunch of drinamyl (a lunatic combination of uppers and downers, sometimes called "purple hearts"), and hatched a bonkers plan to invade Egypt. It caused an international fiasco, blew up in his face, and destroyed his career, while making Nasser a hero to his people. In other words, almost the exact opposite of an assassination.

CCB agents attempted to kill Reverend Frank Chikane by breaking into his luggage and coating all his underwear with deadly poison. This failed, because the underpants were too small to hold enough poison. If they'd put it on his shirt or pants instead, he almost certainly would have died. Still, they got a bunch of poison on a guy's dick, and then found out it wasn't big enough to be lethal.

Meraj Chhaya/Wiki CommonsThat's gotta hurt your pride. CCB gets half points.

After the underwear scheme, the CCB made an attempt to replace a lawyer's heart meds with poison, but failed because the man they hired to do it ripped them off and threw the poison away. It's almost as if you can't even trust guys who claim to be willing to murder people for money!

But probably the most stupidly elaborate plan was their "Bulgarian Umbrella" -- an umbrella that shot poisoned bullets, and served both functions as poorly as you'd expect. While demonstrating how to use it, one CCB agent spilled poison on himself and almost died. Then the umbrella started to come apart, so they had to repair it with hair curling tongs. And while all this was going on, the two men they wanted to kill left town, and the CCB had to throw the umbrella in a river.

That failure hints at a recurring problem: The Soviets were so ruthless that it over-complicated things. It bit them in the ass in 1942, when they recruited a youth named Omer Tokat to assassinate the Nazi ambassador to Turkey, Franz von Papen. Since von Papen was a high-profile figure who had helped Hitler come to power, the Soviets thought this might destabilize relations between Turkey and Germany. But obviously that wouldn't happen if the assassin was caught and confessed to being a communist agent. So the Soviets came up with a brilliant plan: They gave Tokat a device that they said would release a smokescreen to cover his escape, ninja-style. Awesome! But ... not really. The device was in fact nothing but a bomb that would kill the idiot as soon as he pressed the button.

Here's the problem: If you have a kickass James Bond ninja smoke gadget, you're going to use it ASAP. The nervous student fired his gun and hit the smoke button at exactly the same time, and was promptly vaporized. Vaporized. They found his foot on the sidewalk and his penis in a nearby tree. It was circumcised, which made investigators first suspect he was a Muslim, but they found a distinctive wart on a chunk of his forehead.

It turns out getting vaporized screws up your aim, so Tokat's bullet missed, and Von Papen was wildly confused but unhurt. He didn't even know that anyone shot at him. As far as he knew, some nearby guy simply up and exploded. The point is, Tokat probably could have hit him if he had a couple more chances, and that's exactly why schemers should always be honest with their hired killers.

These would have made for some crappy Assassin's Creed Origins stories, huh?

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