5

A Caribbean Dictator Tried To Kill The Pope With Magic

Rafael Trujillo was a toad-faced little prick with the porn star version of Hitler's mustache who ruled the Dominican Republic with an iron fist from the '30s to the '60s. In 1960, the Catholic hierarchy finally turned against his brutal regime, sticking with the Church's strict "30 years of unlimited strikes and maybe you're out" policy. Prayers were altered to include a request to pray for "all those who are suffering in the prisons of the country and their afflicted families." Yes, the people dared to take God's side instead of an evil dictator's. Clearly, this would not stand.

Dominican Press"THIS WILL NOT STAND!"

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.

4

The CIA's Best Assassination Plan Was "Give Poison To Schmucks"

The CIA came up with a bunch of wacky plans to get rid of Fidel Castro, and Cracked has already covered some of the craziest, like cigar bombs, infected hankies, exploding clams, anti-beard poison, and dropping a big anvil on him from a cliff (only one of those is made up). But even when the CIA managed to think of a sane plan, they hired the most bumbling klutzes possible to execute it.

The agency once learned that Castro frequently visited a specific cafeteria to get his milkshake fix, so they persuaded a worker there to slip a poison pill into one of his shakes. They had a guy in Castro's favorite restaurant with a deadly poison ready to go, so it should have been a slam dunk, right? But the would-be assassin had stored the pill in the restaurant freezer for some reason, and when he went to retrieve it, found it frozen to the side. He tried to pull it free, but it ripped open, spilling the poison. Realizing how many things can go wrong in a milkshake murder, the guy got nervous and refused to try again.

Jack Manning/The New York TimesAttemps to poison his milkshakes at the source also failed.

3

MI6 Tried To Kill The Egyptian President With An Exploding Razor

In the 1950s, British Prime Minister Anthony Eden hated Egyptian president Gamal Nasser. He would literally scream into the phone that he wanted the guy "destroyed." But MI6 didn't have much experience killing a well-protected world leader, and weren't sure how to do it. So, being British, they did what came naturally to them: a bunch of silly James Bond shit. That's not even a joke; Eden was close personal friends with Ian Fleming.

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.

APAnother devastating King Farouk burn here on Cracked.com, your home for 20th-century Egyptian leader roasts!

2

South Africa's Hit Squad Tried To Poison Their Enemies' Underwear

The Civil Cooperation Bureau (CCB) was the most blandly named death squad in Apartheid-era South Africa. While they were genuinely horrifying people, the CCB apparently overreached their own evil when they tried to expand from bombs and guns to biological weapons. For the life of them, these racist idiots could not figure out how to do poisons.

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.

via South African History OnlineNo points, CCB. No points.

1

The Soviets Were Too Ruthless To Actually Kill Their Targets

When Yugoslavia's Marshal Tito pissed off Stalin, the Soviets had a Russian spy go undercover as a Costa Rican to get appointed Costa Rican ambassador to Yugoslavia, all so he could infect Tito with weaponized bubonic plague at a diplomatic reception. Weaponized plague at a fancy party. Now that's an assassination plan! Fortunately, it took so long to come together that Stalin died before it could start, and his successors called it off.

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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