Top 10 Prisoners Who Kept Escaping Prison

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As we all know, really creepy murderer Richard Matt and his slightly less creepy murderer friend, David Sweat, escaped from prison recently.

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Using power tools, authorities say it probably took the men about two days to saw through their cells and into the pipe they eventually tunneled out through. The night of the escape, the men positioned dummies made out of sweatshirts to fool the guards, then slid into the pipes, exiting from a manhole located just outside the prison walls.

While none of us like to hear of murderers running free, especially if they are in our neighborhood, there is something about a prison escape that draws us in.

Here are 10 convicts that escaped from prison multiple times.

10. Ted Bundy

bundy-escapes

I mean seriously, how did this happen? Of all people you would not keep a close eye on, you let Ted Bundy escape? Twice?

We all know Ted Bundy, he was the friendly murdering necrophiliac next door, arguably one of the most sickest and dangerous people to ever live. Word is that he killed over 100 women.

The first time he escaped he actually just jumped out of an open window at a jail law library and ran away. He was recaptured a few days later.

So this time they would watch him a tad more carefully. Right? Nope.  He ended up cutting a hole through his cell ceiling with a hacksaw, found some street clothes in a jailers apartment and walked out the door.

He made it Florida, where instead of laying low and hiding out, he slaughtered a whole bunch of women instead. He was soon arrested again and probably watched a tad closer from then on.

9. Brian Bo Larsen

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Larsen is an armed robber from Denmark. Larsen is not nearly as scary as a lot of people on this list and Denmark prisons are relatively easy to escape. They don’t take things all that seriously over there.

Still, with that said, Larsen has escaped from prison 22 times. He usually just cut through his bars and jumped out, but he has used other methods as well, such as as hiding in trash containers. The last time he was caught after crashing a stolen car. He was on drugs and had a hooker with him. He must have gone to the Ted Bundy School of Laying Low.

8. Joseph “Moondyne Joe” Bolitho Johns

moondyne-escapes

Moondyne was originally from Great Britain, but spent most of his time in Australia, where he became a bit of a folk hero for all of his escapades. In Australia there is the Moondyne Festival, and numerous poems and books have been written about him.

He was a petty criminal, a robber and a horse thief, who would have been long forgotten about if he didn’t escape from prison from 5 times. He was the original “bushranger” convict who hid in the Australian bush and robbed to survive, a bit like the “highwaymen” of Great Britain.

7. Richard McNair

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McNair killed a man during a burglary in North Dakota. A few hours after he was arrested, he was handcuffed to a chair. He used lip balm to lubricate his hands free of the cuffs and ran away. He was caught soon afterwards.

After he was sent to prison, he and some other inmates escaped by crawling through an air duct. The other prisoners were caught almost immediately. McNair lasted 10 months before he was arrested.

One would think that would be it, but no. In 2006, 14 years after his last encounter McNair hid in a large box and literally mailed himself outside of prison. Once he was out, he just cut himself out of the box and walked away. This time he last a year and a half on the fun before being recaptured.

6. Jack Sheppard

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Sheppard was a thief in 18th century London. He was known for his drinking and hanging out with what were known as back then as whores. He was basically a petty thief and a pickpocket.

He was arrested numerous times in 1724, and each time he escaped. He would do things like file through his manacles and using a bed sheet to lower himself down to freedom. Sheppard was becoming a bit of a folk hero, he was rather handsome, his crimes were not violent and it seemed that no jail could hold him.

But you know things were a bit different back then. The last time he was caught he was hung.

5. Pascal Payet

payet-escapes

Payet, while almost assuredly a bad person, was without a doubt a bad ass. After being incarcerated for killing a guard during a robbery in France in 2001, one of his associates broke him out of the prison by using a helicopter.

While this is pretty wild, what makes it even more so is that while on the run, Payet came back to the same prison, yes, in a helicopter and broke out some associates of his. He was caught soon after and returned to prison.



So this is it right? No more escapes, no more helicopters.  Wrong. Even though Payet was one of the biggest escape risks in France, and was being moved from prison to prison every 6 months, on Bastille Day in 2007, four masked men hijacked a helicopter and broke him out again.   He was captured soon after and is back in prison where I imagine he spends a lot of time staring at the sky.

4. Steven Jay Russell

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While undoubtedly one of the more brilliant minds on this list, Russell is also one of the more pathetic, as each of his schemes eventually blew up in his face in a horrific way, and most were done so he could be with his boyfriend.  He is the inspiration for the movie “I Love You, Phillip Morris.”

Russell was in prison for a petty crime when he fell in love with his cellmate, Phillip Morris. They were both released, but Russell was soon back in prison again for embezzling a large sum of money. He made his first “escape” when he called the bail office pretending to be a judge, and lowered his own bail from $950,000 to $45,000. He was soon recaptured and sentenced to 45 years.

He escaped by using a highlighter and his cell toilet to make his jail uniform turn green, which was the color of doctor uniforms, and he walked out the door. He was soon recaptured.

He then somehow managed to convince the prison he had AIDS, and contacted a hospice impersonating a prison doctor. He was released, had himself admitted into a false treatment and, later, declared himself dead.

He was eventually caught and sentenced to 144 years.

3. Yoshie Shiratori

shiratori-escapes

Yoshie was arrested for murder and robbery.  Prosecutors sought the death penalty. He wasn’t having that though. Shiratori escaped four times over the years, using methods such as fleeing through air vents and sawing through his floorboards and digging his way out through the dirt with a bowl.

He became a bit of a folk hero while on the run, but eventually tired of the escapee life and turned himself in. He was paroled in 1961 and lived his last 18 years as a free man.

2. John Dillinger

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Dillenger is one of the most well known bank robbers and gangsters in American history. He was responsible for 24 bank robberies before he was captured.

His first break out occurred in a county jail in Ohio when he and a bunch of his associates escaped with guns that were smuggled into the jail. He stayed on the run for another few months before he was recaptured.  He escaped again though, this time using a fake gun that was made out of wood.

Dillinger didn’t go back to jail. He was shot and killed by lawmen when they tried to arrest him.

1. Willie Sutton

sutton-escapes

Sutton was a bank robber who escaped on three different occasions. Over his career he was said to have stolen over 2 million dollars. Because of this and his escape attempts he was known as “Slick Willie.” Like others on this list, he had a good rep with the public, it was said he never robbed a bank if a woman screamed or a baby cried.

Sutton escaped a few times by grabbing a gun and scaling a wall with a ladder but one escape stands out, which was the one he really didn’t have much to do with.

Two inmates,  Clarence Klinedinst, and William Russell, dug a hole 15 feet down, 97 feet long to the road and 15 feet back up to freedom. The tunnel had lights and wood bracing. Sutton was just along for the ride and went out the tunnel with around ten other inmates. He was captured soon after.

Sutton was released later in life and became a consultant with banks on how to avoid robberies and did a TV commercial for a credit card.

To read more about bad guys doing bad things, check out Brian’s book, Raping the Gods on Amazon.


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