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Top Five Ballsiest Criminals of All Time

Sometimes, having a great plan isn’t nearly as important as being a lucky bastard.

We've all heard about criminals stupid enough to try to mug a cop, crack an ATM with a meat cleaver, or look directly at Lady Gaga. They are rightly punished for their errors. But what about the ones who fail upward? Some people, despite or because of their
incredibly poor judgment, actually get away with it, at least until something even dumber trips them up. People like...

Skyjacker: D. B. Cooper
Even though he looks like a Fed, this is one of the most notorious and audacious criminals in living memory. No one has ever figured out Cooper’s true identity.

All we know is that one morning he put on some snazzy clothes and decided to sip bourbon while terrorizing the skies—even though that’s more of a tequila impulse. Cooper strolled up to the airline ticket counter, gave a fake name, and boarded with his carry-on bomb (you can blame this guy the next time a TSA agent inspects your underwear for sexy chemical agents). Midflight, he asked pretty stewardess Florence Schaffner to sit next to him with what had to be the most original pickup line ever: “I have a bomb.” He released everyone but the crew in exchange for $200K (the handoff happened during a pit stop) and some parachutes.

This is where it becomes legendary. Mr. James Bond of Crime decided this hijacked plane wasn’t dangerous enough to hold his interest, so he leapt out of the plane in midflight, rain and low altitude be damned. When your plan involves “hoping they have a parachute and then jumping out of a plane”, even Patrick Swayze can barely get away with it, and yet Cooper apparently did. We like to think he planted a few grand to stage his death, then escaped back to rich anonymity. But even if he died, how does Hell plan on holding him?

Royal Bedroom Intruder: Michael Fagan
Michael Fagan broke into Buckingham Palace… twice. The first time he shimmied a drainpipe past a (presumably saucy) maid. She dutifully called palace security, who—and we’re quoting directly here— “decided not to act.” He spent a half hour eating cheese, then sat on the throne, because: wouldn’t you? England’s new cat burglar king abdicated when he got drunk and tired, and left the palace on his own.

Since it went so well the first time, he decided to return, because there are worse hobbies than terrorizing elderly aristocrats. Plus it was the Thatcher years, so it was a good to remind the government that the poor had yet to be destroyed. Waking up the Queen for a chat, he disturbed a silent alarm (which was ignored, possibly because the police were busy not responding to Her Majesty’s two phone calls for help). Then he bummed some smokes from her because, again: wouldn’t you? At this point, guards had no choice but to do their jobs, but rather than having his head lopped off for committing treason, he simply ended up with a six-month stint in a psychiatric hospital.

Art Thief: Vincenzo Peruggia
Quelle Horreur! That’s French for “Wasn’t the Mona Lisa here a minute ago?” When the Mona Lisa was stolen from the Louvre on August 21, 1911, it took two years and a stroke of luck for the culprit to be revealed as a patriotic Italian.

A former Louvre worker, Peruggia simply hid till the coast was clear, smuggled the painting out under his artist’s smock, and walked out past an empty guard box (this saved an awkward explanation about why his torso was so square - the Mona Lisa’s painted on wood, not canvas). So simple it’s brilliant, right? (And we mean “simple”: “walking in and hiding it under your coat” ranks up there with “I’ll just write a fake suicide note” for disguising a beheading as a subtle and ingenious plan.)

Peruggia hid the painting in a false trunk, told police he was nowhere near the crime scene, and left France scratching its head with a clean getaway to his native Italy. Now for the really dumb part: Assuming his countrymen would be thrilled to once again own a treasure pilfered by that Corsican bastard Napoleon, he cold-contacted an art dealer. It’s sad, because there can’t be much practice for casually offering to sell someone the most famous painting of all time. One confirmed viewing later, Peruggia was in cuffs, and Mona was touring the country to great acclaim (so in that regard, he was right). Italy can’t sincerely punish a crime of passion, so he skipped through a measly six-month jail term. The kicker? He returned to France and opened a paint store in a forgiving neighborhood.

Chinatown Gangsta: Mock Duck
Let’s be clear that Sai Wing Mock, a.k.a. “Mock Duck,” was, in most regards, a really competent crook.

The dude was barely 20 when he put the screws to Chinatown’s top gangster, and already had a penchant for having his rivals decapitated with hatchets, meaning Kung Fu Hustle was more historically accurate than it looks. One war grew so bloody the U.S. and Chinese governments had to negotiate a truce and let Mock walk away. Atop this mountain of evil success, The Mayor of Chinatown did one really, really dumb thing: he fought his gun battles by squatting in the street and closing his eyes. Somehow it worked, but that’s not bad-ass, that’s just getting lucky in a stupid way. The only time he ever lost was when three opponents pulled the same tactic on him. Heck, maybe there’s something to it.

Marathon Faker: Rosie Ruiz
Fraud is the least of the crimes in this list, but ask yourself, “Who do I want to kick in the shins? One of the adventurers, guilty only of living out our dreams (and shattering lives forever)? Or a dirty cheat?” Rosie Ruiz skimmed the New York Marathon, by taking the damn subway. Granted, in 1979 that was even more hazardous than running 26 miles, but c’mon.

Without crossing the finish line, she qualified for Boston, where she “ran” the third-fastest marathon in history with her focus, winning attitude, and lies. Beantown politely asked, “Hey…whyn’tcha sweatin’?” and only then did anyone question her New York finish. So basically, all she had to do was feign an injury and quit while she was ahead. Or at least not pretend to hurdle the limits of human endurance.

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