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Five Prisoners Who Kept Escaping Prison

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College graduate, freelance writer, cooking aficionado. Political junkie by day and screenwriter by night.

Prison escapes have been taking place all over the country and throughout America's history. In 2015, murderers Richard Matt and David Sweat escaped from the Clinton Correctional Facility in upstate New York. They managed to escape using power tools and sawed through their cells and into a pipe they tunneled through. The men ended up using dummies to fool the guards. They escaped from a manhole just outside the prison walls.

While none of us want to learn of dangerous men escaping from prison and walking around our neighborhoods, these are five convicts that escaped multiple times.

5. John Dillinger

John Dillinger has become one of the best-known bank robbers and gangsters in American history. Law enforcement has tied 24 bank robberies to him before he was captured. His first escape was from a county jail in Ohiowhen he and his cohorts escaped with guns.

He managed to stay on the run for several months. After his recapture, he used a fake wooden gun to escape. Dillinger ended up being shot and killed by law enforcement when they tried to capture him.

4. Jack Sheppard

Prison escapes have been around for centuries. Jack Sheppard was arrested and put in prison for being a thief and pickpocket. In 1724, he managed to be arrested multiple times. Each time he was sent to prison, he managed to escape. He used a handful of different ways to escape, including using a bed sheet to lower himself to the open world. Sheppard was a folk hero and it seemed no prison could hold him.

3. Willie Sutton

Willie Sutton escaped from prison three times. He was a bank robber, who stole more than $2 million dollars throughout his career. He was given the name "Slick Willie" for his multiple escape attempts.

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Sutton escaped multiple times by a variety of methods. One particular escape that can't really be attributed to him was when two fellow inmates dug a massive tunnel. The tunnel had lights and wood bracing. Sutton was just there for a ride, but ended up escaping with 10 other prisoners.

Sutton was quickly captured and was later released from prison. He ended up being a consultant with banks.

2. Brian Bo Larsen

Brian Bo Larsen is a Danish armed robber. Larsen probably has the record number of prison escapes with 22. Denmark prisons have been said to be easy to escape from. Larsen escaped prison by cutting through his bars and hiding in trash containers. During his last escape, he was caught after he crashed a stolen vehicle. Police found him on drugs and with a hooker.


1. Ted Bundy

Probably the most evil person to escape from prison was Ted Bundy. Many question how he was able to escape twice. Ted Bundy is definitely one of the most evil individuals to ever live. He ended up killing more than 30 women.

Bundy's first escape was from a jail law library, but he ended up being captured days later. Ted Bundy later escaped by cutting through his cell ceiling. He switched out his prison uniform with street clothes he found in a prison apartment and walked right out the front door.

© 2019 Lawrence

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