We know that in real life, crime isn't as fancy as it is in the movies. Heists aren't carried out by slick operators in tuxedos, but by strung-out dudes looking for meth money. And in real life, most prison escapes aren't the result of mind-blowingly complex schemes, but a combination of dumb luck, indifferent guards, and unintentional hilarity.
5A Notorious Serial Killer Asks to Study Law Books, Then Just Walks Out
Unless you're confusing him with the father in Married: With Children, you know who Ted Bundy is. One of the most iconic American serial killers, Bundy terrorized the U.S. in the 1970s. Early in his career, Bundy was arrested in Colorado, where he waived his right to an attorney and decided to represent himself in court. This turned out to be the first step in an escape plan straight out of some wacky movie where the villain is played by Larry the Cable Guy.
Since Bundy was the lawyer as well as the accused, the judge excused him from wearing restraints so he would be able to move around the courtroom. You know, so he could do lawyer stuff. Then, during a court recess, Bundy was given permission to visit the courthouse's library, alone, to brush up on his lawyering. Come on, it's not like you can deny that request. The guy has a tough job. His client is a serial killer.
Although his greatest crime was that unibrow.
Sure enough, as soon as he was left unsupervised in the library, Bundy jumped out of a second-story window and escaped. See, this is why we don't guard serial killers using the honor system anymore.
Wait, it gets worse. Within six months, Bundy was caught again and his trial resumed. At this point, legal advisers told him to stay the course, because the prosecution's case was weak and he was likely to get off. Despite this, Bundy devised a crafty if cliched escape by slowly sawing a hole in his cell's ceiling. Then, on Christmas Eve, he hid books under his blanket to imitate a body and escaped through the ceiling.
It turns out that the ceiling led right to the apartment of the chief jailer, a situation that stupidly worked in Bundy's favor, because said jailer was out that night on a date. Bundy raided the guy's closet and stole his clothes, then simply walked out the man's front door to freedom, escaping to the retirement state, Florida. According to his later confessions, he intended to stop serial killing. Then, after he serial killed some more people, we executed the crap out of him. He really did forever ruin our ability to trust serial killers.
4A Greek Bank Robber Escapes Prison Via Helicopter (Twice)
Vassilis Paleokostas is considered a kind of Robin Hood figure in Greece, although with a much less catchy name. Having committed a series of bank robberies and ransom kidnappings (and reportedly sharing his loot with the poor), his luck eventually ran out when he was caught and sent to prison. We can't say whether or not a corrupt wolf sheriff was responsible.
From the story you're about to hear, this is probably closer to the mark.
But Paleokostas didn't stay behind bars for long. In 2006, he and an accomplice broke out, not through some daring Shawshank Redemption caper, but by simply getting his brother to land a freaking helicopter in the prison exercise yard and pick him up. The guards' excuse for allowing this insane plan to succeed was that they thought it was an impromptu visit from prison inspectors, given that nobody would be insane enough to try to escape prison in a helicopter. You know, because prison inspectors are more likely to make a surprise helicopter landing in the exercise yard and start lobbing smoke grenades at the staff.
The fugitives went right back to committing crimes until they were recaptured two years later. But it didn't last this time, either -- Paleokostas and his henchman were still days away from being tried for their previous escape when, in February of 2009, they escaped from the same prison a second time (and yes, we're serious) in another helicopter.
"There is elegance in simplicity. And also in helicopters."
Greek authorities are understandably a little embarrassed by this, and Paleokostas remains at large. You have to admit, it really doesn't seem like the sort of thing that would happen twice.