10 People Who Have Escaped From Prison More Than Once

10 People Who Have Escaped From Prison More Than Once

There is something about the prison escape that gets the blood circulating.  These dangerous guys were put in prison for a reason so we, as a society, are safe. Right? Well not all the time. Sometimes these murderers, rapists and robbers escape which then causes mass panic.

Recently, murderers Richard Matt and  David Sweat escaped from prison and it became news all over the world. Matt was killed, while Sweat was captured and returned to prison. The two used power tools to saw through their cell walls and into a pipe and then eventually tunneled out through.  They put dummies  in their beds made out of sweatshirts to fool the guards, then went through the walls and exited from a manhole. 

Even though they were caught, they still made a daring escape and were famous all over the world for doing so. But they only escaped once. A few prisoners have escaped more than once, and that takes some doing. Some are minor criminals who became folk heroes for all of their escapes, some are terrifying murderers that never should have seen the light of day again.

10. Ted Bundy – Jumped Out Of Window

Wait a minute. Ted Bundy escaped twice?  Of all the horrible people that were in prison, this psychopath escaped..twice? Yes, he did.

Word is that Bundy killed over 100 women. He was one of the sickest people to ever roam the Earth. The first time this murdering necrophiliac escaped, he jumped out of a window while at a law library and just ran off. He was quickly captured. The next time he was a little more subtle. He  cut a hole through his cell ceiling with a hacksaw, and escaped in clothing he stole from a jailers apartment.

He then went to Florida, where he killed more women before he was caught again. I imagine after that they paid a little bit more attention to him.

9. Steven Jay Russell – Escaped For Love


Russell escaped quite a few times just so he could be with his boyfriend, whom he met in prison. The story is so odd that it inspired the movie I Love You Phillip Morris.

Russell was in prison for fraud. After he and cellmate Phillip Morris fell in love, they were both released. That could have been the end of the story but Russell was soon back in prison again for embezzling. He simply could not stand to be without Morris and escaped by calling the bail office, pretending to be a judge, and lowered his own bail from $950,000 to $45,000. He was caught but then escaped by impersonating a doctor and walking out the door before being recaptured.

This last one takes the cake though: He convinced the prison he had AIDS, (he didn’t) and was released, to a treatment center that didn’t exist ( he had set it up pretending to be a prison doctor. He later tried to declare himself dead. He was caught and sentenced to 144 years.


 8. Richard McNair – Mailed Himself Out Of Prison


McNair was a bad man. After killing a man during a burglary in North Dakota, he was arrested, and handcuffed to a chair in a holding area. Somehow he used lip balm to free himself from his handcuffs and ran away.

He was caught and sent to prison for the murder. Once again, he escaped by crawling through an air duct and made it 10 months before being caught. Two prison escapes is enough right? Well, not for McNair. He put himself in a large box and  mailed himself outside of a prison. No, that isn’t a joke.  Then he got out of the box and walked away. He was free for over a year before he was busted yet again.

7. Willie Sutton – The Famous Escapee


Sutton was a well known and successful bank robber. He was said to have stolen over $2 million during his bank robbing days. He was known as Slick Willie, and had a soft side for a reputably bad guy. Sutton allegedly called off bank robberies if a woman screamed or a baby cried.

Sutton escaped a few times from prison: once he got control of a gun, and another time he scaled a wall with a ladder. His most famous escpape, though, he was just along for the ride. Some prisoners dug a hole 15 feet deep and almost 100 feet long. The tunnel even had lights. Sutton escaped with around 10 other guys but had nothing to do with digging the hole.

Sutton became a consultant with banks on how to avoid robberies later in life, and even did some TV commercials.

6. Pascal Payet – The French Love Their Helicopters

Payet took breaking out of prison to a whole new level.  In 2001, while in prison for killing a bank guard during a robbery, one of his gang members broke him out of the prison by using a helicopter. Then while on the run, Payet got in a helicopter, came back to the same prison he broke out of and broke out some other prisoners. He was caught and went back to prison.

You would think that’s where the story ends for Payet, but it doesn’t. In 2007, some men yet again arrived via a helicopter and broke him out again. He is now back in prison where I imagine he doesn’t spend too much time outside.

5. Jack Shepard – The Bed Sheet Escape

Shepard was a a petty thief from London. He was known for his drinking and hanging out with women. He was arrested numerous times in 1724. Every time he would be arrested for a minor crime, he would escape. One of his more well known escapes was when he used a bed sheet to lower himself down to freedom. Since he was charming, handsome, and his crimes were not violent, he became a bit of a folk hero. The law wasn’t impressed though. The last time they caught him after an escape, he was hung.

4. Brian Bo Larsen – 22 Is His Magic Number


Brian Bo Larsen is from Denmark and was in prison originally for armed robbery. Remarkably, the man  has escaped from prison 22 times. Obviously folks in Denmark don’t take things like prison escapes as seriously as we do.  Sometimes he cuts through bars, other times he hides in trash cans. When he gets out, he has fun. One time he escaped he had crashed a stolen car while with a prostitute and high on drugs. Last heard he was back in prison, but will probably be back out soon.

3. Yoshi Shiratori – The Innovative Escape Artist

Yoshi murdered a man during a robbery in Japan. Shiratori escaped four times over the years. He got out through air vents; he would saw through his floorboards; and he once dug his way out by using a bowl. He even escaped by rusting his handcuffs with miso soup.

He was a free man for a long time, but got tired of life on the run and turned himself in. He was good this time and was eventually paroled. He lived his last 18 years of life free, outside of prison.


2. Moondyne Joe – The Folk Hero

Born as Joseph Johns in England, Moondyne Joe was a petty criminal. His crimes were pretty basic: he was a robber and a horse thief. At one point, the criminal was transfered to the penal colony of Western Australia. So what was the big deal about this man? Well, he escaped from prison 5 times.

That sort of feat gives you respect in Australia where Moondyne Joe now is a folk hero. In fact, there is something called the Moondyne Festival which was named after him. In addition, many poems, songs and books have been written in his honor. He died a free man.


1. John Dillinger – Escaped Using A Wooden Gun


Dillinger is well known for being a bank robber; he is one of the most famous of all time. He robbed well over 2o banks before being caught.

His first escape came was from a county jail when he and a bunch of his gang members escaped with guns that were smuggled to them. Really? How did that happen? He was recaptured, then escaped again. This time he was using a fake gun that was made out of wood. Well I guess if you had already escpaped with a real gun it makes using a fake one easier. He was shot and killed when the police arrived to arrest him.




10 People Who Have Escaped From Prison More Than Once

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