Some of the most daring prison escapes of all time

In most parts of the world, prison isn’t meant to be a fun place. You don’t typically wind up in one because you did something good. If you’re in prison for a long time, you probably stole from someone or killed someone. Basically, prison is not enjoyable.


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It would make sense, then, that people would want to do everything they could to get out of prison. Some even create elaborate schemes akin to those you might see in some sort of AAA blockbuster starring Nicolas Cage or Steven Seagal, maybe even both.

When these real life prison escapes do happen, they draw the attention of many. Some can be mundane, but some really are things of beauty.

Click ‘Start Slideshow’ and see what’s behind these amazing prison escape stories!

Escaping the Tower of London

Way back in the sixteenth century, a Jesuit priest named John Gerard was locked away in the inescapable Tower of London. Well, supposedly inescapable. As a Jesuit priest, he followed the Catholic Church, which wasn’t particularly well liked in England. Using invisible ink made of orange juice, Gerard worked with his allies to climb down a rope tossed up by his helpers and into a boat they had waiting in the tower’s moat.

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Dillinger Gets Crafty

John Dillinger is a name associated with crime in the 1930s. He was a notorious bank robber, and was caught more than once. In 1934, he was picked up and locked away in Lake County Jail, which was guarded by an army of officers and was believed to be escape-proof. Apparently, Dillinger got crafty and carved a gun out of a bar of soap which he then used to steal the sheriff’s car and drive away.

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The Libby Underground

One of the greatest prison escapes goes all the way back to the Civil War. In Richmond, Virginia, there was the Libby Prison. In 1864, it housed a number of Union soldiers, and together they dug a tunnel through the prison’s basement and into a lot nearby. While only 59 of the people who escaped that day actually made it to safety, 109 made use of the tunnel. The rest of that group were recaptured, and two drowned.

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The Loverboy’s Great Escape

Leading a tawdry life could land you in jail back in the 18th century. Just ask Giacomo Casanova. Yes, that Casanova. He was imprisoned in the lead-roofed Leads prison. He managed to smuggle in a metal spike and used it to tunnel through the ceiling of his cell, get up onto the lead roof, then into another room before finally maneuvering to the ground floor and onto a gondola to freedom.

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Escape By Chopper

Pascal Payet managed to escape his French prisons with style. Both times, he was whisked away by helicopter from the prison’s roof. The first time was in 2001, after he was imprisoned following a murder conviction. French prisons tend to have exercise yards on the roof, so the chopper simply came in and picked him up. The same thing happened in 2007 when he was picked up in a hijacked helicopter and vanished.

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Escape from Laos

One man, a Navy pilot named Dieter Dengler, was shot down over Laos in 1966 and was imprisoned. During training, Dengler would often escape any POW camp situations. The same held true when the real thing came along. Dengler and a few prisoners managed to get free of their restraints and take out a couple guards before heading into the jungle. Dengler and one other survived for 23 days in the jungle before being rescued.

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Getting Out of The Rock

You can’t talk about prison escapes without mentioning Frank Morris and Clarence and John Anglin. In 1962, the trio escaped from Alcatraz. Theoretically, anyway. Using various tools constructed from things they had managed to smuggle away, they drilled through their cells into some ventilation shafts and eventually to the beach where they made a raft. Their absence wasn’t immediately noticed since they had made dummies to trick the guards. It is believed they may have drowned.

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The Maze Prison Escape

The Maze Prison experienced more of a riot than an escape in 1983 after 35 inmates took over the prison before getting free. While it was supposed to be one of those most secure prisons in Europe, the Irish Republican Army proved that wrong when a group of them planned and executed an escape using smuggled in guns. Guards were wounded, uniforms were stolen, and a fair chunk of them actually got away.

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The Midnight Express

Well, if you don’t want to go to jail, you probably shouldn’t try to smuggle drugs like Billy Hayes who was arrested in 1970 for trying to get some hash out of Turkey. To be fair, Turkey’s prisons are pretty harsh, and it makes sense he might want to escape. He hid out for some time on the island prison where he was held before stealing a dinghy and making his journey back to the United States.

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The Great Escape

Back in 1944, 76 allied soldiers made a dramatic escape from a German prison. It took nearly 600 prisoners a year of work to make the escape happen. Three tunnels were made under the main fence of the prison. The tunnels were impressive, filled with supports, lamps and pumps for air. When the men made their escape, the tunnel ended short of the forest so they were seen. Most were caught again. The story was turned into a film.

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Squeezing On Through

Thinking about the method used by 50-year-old Choi Gap-Bok to escape prison makes my entire body hurt. The man escaped through the food slot on his the food slot on his prison door. I don’t mean he used it, I mean he went through it. He put his head through, then compressed his body enough to slip on out. He made it out in 34 seconds, but only enjoyed six days of freedom before being caught again.

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The Bedsheet Rope Trick

Jack Sheppard invented the bedsheet rope trick. Probably, anyway. On at least two occasions, Sheppard was imprisoned and tied the sheets of his bed together to escape his prison cell. The first time, he had to break through his ceiling to do it. The second time, he and his wife went out a window. As simple as it is, I suppose someone had to be the first to do it.

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The Prison Inspector

Catch Me If You Can is one of my favorite films. The way Frank Abagnale keeps the police on the run for years is very exciting. The real Abagnale also made a daring escape in 1971 after he convinced the guards he had been sent into the prison as an undercover inspector. He was treated very well while in prison, then worked with a friend outside to help him walk right out the front door.

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Abagnale posing as a pilot

The Escape of the Master Craftsmen

If you can’t steal the equipment you need to get out of prison, why not make it yourself? Three men did this to escape Parkhurst Prison in 1995. First, they made a 25-foot steel ladder. Then they built a gun. Then they made a key which they used to unlock every door they needed to go through to leave the prison. By all accounts, this key was likely made from memory after seeing the key used by the guards.

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The Death Camp

Sobibor Death Camp, as its name implies, was an awful place, but one prisoner had had enough. He worked with a group of other prisoners to create various weapons in the prison’s shops in order to execute a plan: kill every Nazi in the place. When the time was right, Leon Feldhendler and his crew used their weapons to take out every Nazi in the prison, leaving only the Ukrainian guards. Not everyone escaped, but a fair chunk did.

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The Survivors

The Disappearing Serial Killer

Authorities really should have kept a better eye on Ted Bundy, the well known serial killer. Bundy represented himself during one of his trials and, during a recess, asked for permission to go to the court’s library to look something up. Unsupervised, Bundy climbed out a window and escaped. He was caught again in six months, at which point he again escaped by climbing through a hole in the ceiling of his jail cell.

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More Helicopter Escapes

Perhaps taking a page from France’s helicopter escapes, Vassilis Paleokostas in both 2006 and 2009 escaped from a Greek prison by hopping into a helicopter which had landed in the middle of the prison yard. The first time, at least, guards figured it was just an unscheduled visit by prison inspectors. I’m not really sure what happened the second time, as they were both in the same prison.

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Well Dressed for Escaping Prison

A nice set of clothes got Charles Victor Thompson out of prison. He smuggled some clothes in, called his lawyer to set up a meeting, then walked out the unlocked door when his lawyer left. In his new duds, nobody paid much attention to him. He approached the guard booth, said he was with the attorney’s office and needed to leave, showing them his inmate badge when prompted for identification. The guard didn’t notice and let him leave.

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Locked in the Loo

You’ve got to love a criminal with style. Jewel thief Alfie Hinds escaped from prison several times, but one was of note. His second escape came when he was taken to court for a lawsuit filed against the officers who arrested him. He asked to be taken to the restroom, where a padlock had been hidden away. He had his handcuffs removed, then shoved the guards into a stall and locked them in with the padlock.

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The Repeat Escapee

Richard Lee McNair apparently really didn’t like to be in prison. He escaped on three separate occasions. The first time, he used lip balm to slip out of his cuffs while sitting with three detectives. The second time, he went through the ventilation system of his prison. The final time, he literally mailed himself out of prison after climbing inside a mailbag he had repaired as part of his work.

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Getting Handy

One of the more recent crimes, 19-year-old T.J. Lane made his way out of prison, along with a couple other inmates, by building a ladder out of junk they found in a warehouse to which they discovered they had access. On September 9, 2014, the group climbed the ladder and onto a building, then jumped over the prison wall and ran. They were only out for about nine hours before they were back in prison.

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The Texas Seven

When it comes to Texas prison breaks, the escape of the Texas Seven is probably the most well known. In December of 2000, seven prisoners, lead by George Rivas, overpowered prison staff, stealing their clothes and vehicle keys. They then managed to get weapons from other guards, who they then tied up. Finally, they drove out in a truck. The group went on a crime spree across the state and into Colorado before they were caught or killed.

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Have a Nice Day

A cordial note was all which was left behind when Richard Matt and David Sweat escaped Clinton Correctional Facility in tunnels they had dug. They first used tools to cut through the steel walls of their cell, then apparently got to digging. They left behind a note which read “Have a Nice Day.” Less than a month later, Matt was shot and Sweat was back in prison.

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Saving Lives

One prison escape eventually resulted in the rescue of 120,000 people. Alfred Wetzler and Rudolf Vrba managed to escape Auschwitz by covering themselves in tobacco and gasoline, to hide their scent from dogs, and hiding in a wood pile before escaping in stolen clothes. Wetzler had with him a report detailing the goings on in Auschwitz, information which led to the bombing of various Nazi officials and the release of the prisoners.

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The French Lovebirds

Yet another helicopter escape happened in France when the wife of Michel Vaujour learned how to fly a helicopter so she could bust him out of prison. Nadine Vaujour landed on the roof of the French prison as Michel made his way to the roof using nectarines which had been painted to look like grenades. They flew away, landed the chopper, and went on the run. Both were eventually caught.

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Michel Vaujour

The Escape of El Chapo

Back in 2001, the Sinaloa Cartel leader Joaquin “El Chapo” Guzman escaped prison by using a laundry cart. He was arrested again in 2014 and made an even more incredible escape. From within a shower, El Chapo gained access to a mile-long tunnel, complete with lights and ventilation, which he traversed on motorcycle which rode on rails. He was picked up again in January of 2017.

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Napoleon Leaves Elba

Going back in time, you might be interested to know Napoleon made a great escape himself. After being exiled to the small island of Elba, Napoleon knew he would have to do something more to stop his enemies, so he gathered up some loyal soldiers and made his way back to France, where he recruited the soldiers sent to stop him. Then Waterloo happened and he finally was sent to a prison from which he couldn’t escape.

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An Inside Job

When several hundred Taliban inmates escaped from prison in Kandahar City, people suspected there was something fishy going on. The prisoners had tunneled through their cells, digging some 1,050 feet away into an abandoned house, all without being seen. It was suspected to be about five months worth of digging. Additionally, the jailbreak was discovered just after all the prisoners had safely escaped. Because of this, many believe prison staff were involved.

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The Long Walk

Polish soldier Slawomir Rawicz was arrested by the Soviet Union on November 19, 1939. After questioning, he wound up in Lubyanka prison in Moscow. He was sentenced as a spy and was sent to a Siberian prison camp for 25 years of hard labor. One and a half years later, Rawicz and six other prisoners apparently managed to sneak out during a blizzard and made their way south, traveling for nearly a year before stopping in India.

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