Three Guys Who Make Prison Escapes Look Like Child's Play

It’s really hard to escape from prison… right? Well, maybe nowadays. But before experience and technology allowed prisons to become the fortresses they are today, it wasn’t as difficult as all that. At least, these guys made it look pretty easy. Here are a few prisoners who managed to escape multiple times.

Jack Sheppard

Not to be consused with Jack Shephard from Lost. This Jack Sheppard was a robber in London in the early 1700s. He escaped from prison not once… not twice… not even three times. He escaped four times before finally being hanged for his crimes. His first arrest for theft resulted in his hand being branded, which was common for the time. The second arrest landed him in St. Giles’ Roundhouse, which only lasted for about three hours. He broke through the shoddy ceiling and climbed to the ground by using sheets – just like the movies. When he got to the ground, he managed to blend in with the crowd that had formed below and created a diversion – he started pointing at the roof and yelling that he could see the prisoner, then scooted off in the resulting chaos.

The second time, he was arrested for pick-pocketing and his wife was thrown in the cell with him (as an accomplice, I suppose). They were sent to the New Prison in Clerkenwell, but managed to file through their manacles before long, removed a bar from the window and again used the sheets to climb down. Then they climbed a 22-foot wall to complete the escape.

Arrest #3 came after he robbed from his former mentor in carpentry. He was arrested just east of the Tower of London. He was sent to Newgate Prison, but, as usual, not for long. When he had visitors one day, they distracted the guards while Sheppard loosened a bar in the window. He later escaped by removing the bar and then changing into women’s clothes (also thanks to his visitors) so he could just walk away unsuspected.

The fourth arrest sent him back to Newgate, this time to a strong-room called “The Castle”, where he was given leg irons and chained to the floor. By this point, he was getting a little arrogant in his escape abilities and pretty much just laughed at the guards. He showed them how silly their shackles were by finding a small nail on the floor and picking the lock that held him. Their response? More secure cuffs and tighter bindings.

Maybe Houdini should have called himself “Sheppard” (not quite the same ring, I know), because Sheppard escaped again. He picked the lock to his cuffs and removed the chains, but was unable to remove the leg irons. He climbed up a chimney, only to find a bar blocking his way. No matter; he just removed the bar and used it to break through another ceiling. Apparently he broke through six doors until he made his way to the roof of Newgate, made his way to the roof of the house next door, broke into the house, went down the stairs and escaped onto the street without waking anyone up. Keep in mind he still had his leg irons on. Those were removed a couple of days later when he bribed someone to bring him blacksmith’s tools. At such an unbelievable escape, a rumor started circulating around town that the Devil himself helped Sheppard escape.

His luck ran out after arrest #5, though. He broke into a pawn shop and stole some finery, including a suit, a sword, rings, watches and other jewelry. He was sent back to Newgate where he had round-the-clock guards and was loaded down with 300 pounds of weights. Up to 200,000 people showed up to see him hanged, but not because they were happy to see him die. No, the public actually thought he was great and even petitioned the King to free him. But to no avail. He was hanged for 15 minutes. Even after that, he had one more plan: his friends were to obtain his body quickly and take him to a doctor, who would try to revive him. But the crowds were so huge that his friends couldn’t reach him, and finally, Jack Sheppard met an unescapable end.

Alfie Hinds

No doubt it’s hard to contain a member of Mensa, who can probably run rings around the thought processes of most of us. Alfie Hinds was another Brit who managed to escape the law over and over again – a total of three escapes. Four if you count his final, legal escape.
Alfred Hinds came by his thievery honestly – his dad actually died while being punished for armed robbery. In 1953, he was arrested for a major jewelry robbery - $90,000 worth of which was never recovered. He was sentenced to 12 years, but somehow escaped through locked doors and over a 20-foot prison wall. The public started calling him “Houdini” Hinds (crap, and I thought my reference in the Jack Sheppard story was original).

He made an honest living as a builder and decorator across Europe until 1956, when Scotland Yard detectives tracked him down and arrested him again. Whatever. It wouldn’t keep him down long. When two guards escorted him to the bathroom and removed his handcuffs so he could take care of business, Alfie shoved them into the stall and locked it with a padlock (accomplices had installed screw eyes onto the door so he could do this). He was captured at the airport only a few hours later.

His third escape was from his Chelmsford Prison. This time he stayed under the radar and worked as a car dealer for more than two years. His downfall came once again when he was pulled over for being in an unregistered car (I bet that police officer was surprised at such a catch). This time, he used his smarts to find a loophole in the law – at the time, prison escapes were not considered misdemeanors, so no time was added onto his original sentence. He finished out the six years from his jewelry theft sentence in 1953, won a libel suit against the arresting officer, and spent the rest of his life as a minor celebrity. Oh, and he joined Mensa, of course.

John Dillinger

John Dillinger spent some time in jail in Lima, Ohio, in 1933, but escaped. It really wasn’t a clever escape: his cronies busted him out by killing the jailer. Escape #2, however, is pretty entertaining. It’s also pretty well known, so stop me if you’ve heard it (it won’t do you any good, though).

In 1934, Dillinger was in the county jail of Crown Point, Indiana. The jail was called “escape-proof”, but as the Titanic taught us, you could never put a definitive disclaimer on anything. J.D. carved a gun out of a piece of wood (some reports say it was a block of soap), blackened it with shoe polish and threatened to shoot the guards with his “gun”. The ruse worked. He escaped and lived to rob for another four months.

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I have met the Hinds family and done extensive research. You failed to mention that Hinds was innocent of the crime his was imprisoned for and whilst "on the run" he would risk capture by meeting with the press to plead his innocence.
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