25 Unbelievable Prison Escapes That Actually Worked

We’re going to kick off this list with quite a doozy, the escape from Nazi Germany prisoner of war camp, Stalag Luft, also known as The Great Escape. The idea came from Squadron Leader Roger Bushell to dig three tunnels named Tom, Dick, and Harry, in hopes one would eventually lead out. Utilizing 600 men, they dug very small tunnels 30 feet deep just enough to get men to crawl through. Eventually, Harry was successfully completed, and 76 prisoners crawled to freedom. Unfortunately, it didn’t last long. Of those that escaped, only three made it to safety.

In 1941, Sławomir Rawicz was imprisoned in a Russian gulag. Escaping with six others and traveling on foot south through the Gobi Desert, Tibet, and the Himalayas, he finally reached safety in India. Except, maybe none of that really happened. Years later, a reporter indicated Soviet documents proved Rawicz was at their gulag, and that he was released to an Iranian refugee camp due to a 1942 amnesty program. School is still out about if he falsified his account, but yeah, it doesn’t look good.

Considered one of the most escape-proof prisons in Europe, Her Majesty’s Maze Prison housed many Provisional Irish Republican Army, or IRA, soldiers. In 1983, Bobby Storey and Gerry Kelly, two IRA inmates, watched for security weaknesses and finally took advantage of them, taking over part of the prison, dressing up as guards, and taking hostages. Overall, 35 prisoners escaped, the biggest prison breakout in British history.

Joaquin “El Chapo” Guzman is a major Mexican drug lord responsible for smuggling tons of cocaine into the United States. In 2001, he was in a maximum security prison in Mexico where he held significant influence over everyone, including the jail director. Using that influence, he escaped and was on the run for almost thirteen years before being captured again. They didn’t hold him long, though. He escaped a second time, finding a tunnel that brought him to a construction site a little outside the prison. Of course, he was caught again and has yet to escape a third time.

All violent prisoners at Kingman Arizona State Prison, John McCluskey, Daniel Renwick, and Tracy Province worked with McClusky’s first cousin Casslyn Mae Welch to break them out. On July 30th 2010, she parked in the back of the prison, threw wire cutters over the fence and other tools to help them escape. They cut a hole through the fence and made a run for it. Renwick took the getaway care while the others walked 8 miles on foot and hijacked a truck. Renwick was arrested first and in less than a month the rest were arrested as well. Arizona officials concluded that it was because of prison negligence that they were allowed to leave so easily. 

Henri Charrière, nicknamed “Papillon,” was a french writer and convict. He wrote the autobiography Papillon about his escape attempts from several European prisons over his lifetime before escaping once last time and becoming a citizen of Venezuela. Critics have insisted that most of what he wrote about probably didn’t all happen to him and were likely stories he heard while in prison.

Serving consecutive life sentences for walking into a school cafeteria, shooting and killing three students, T.J. Lane was not put in a maximum security prison – a big mistake. Using wood from cabinets, he built a 13-foot ladder with two other inmates, climbed up to a roof, and jumped down fifteen feet, breaking out of the prison. However, they didn’t make it too far and were all captured within nine hours.

The Texas Seven were a group of convicts in a Texas maximum security prison that broke out. Overpowering employees and security guards in the maintenance shop, they stole a bunch of supplies and took off. A massive manhunt ensued but they remained without capture for over a year, robbing stores, killing more people, and creating all kinds of chaos. In 2001, they were on America’s Most Wanted, and after seeing the episode, a man tipped off the police where the men were hiding out, leading to their arrest.

Alcatraz is perhaps the most famous maximum security prison in American history and in its entire lifetime only one recorded prison break had ever successfully been completed, and we’re using the word “successful” loosely. Clarence and John Anglin and Frank Morris methodically planned out their escape, creating dummies, building rafts, and digging holes using materials found all over the prison. In the summer of 1962, the men escaped without detection, crossing with their raft over to Angel Island. Prison guards didn’t notice they were gone until that morning. A massive search went underway, but all they found was a boat paddle and Anglin’s wallet wrapped in plastic. Whether or not they made it out alive is up for speculation, but many believe there’s enough evidence to prove they were successful.

During the Greek economic crisis, Vassilis Palaiokostas thought the banks were responsible for their greed and corruption. He decided to make them pay. Robbing millions of Euros from banks and then handing all the money out to the needy, he became known as the “Greek Robin Hood,” but of course it caught up with him. In 2006, he was convicted of robbery and kidnapping and sent to serve a life in prison. While in prison, he hired a few men to hijack a helicopter, fly into the prison, and get him out. It worked. After being recaptured 2 years later, he was sent back to prison, but that didn’t last long. In 2009, he escaped again by helicopter. He’s still at large, known as an uncatchable folk hero.

At 59, Bruce Walter Keith lived an ordinary life in Florida, getting married and working for an air conditioning company. Except his real name is James Robert Jones, a murderer, and fugitive. Escaping one of the toughest prisons in the country, Fort Leavenworth, he went to Florida and remained a fugitive for 40 years. Marshals caught him through face recognition technology.

Auschwitz was the of the most brutal concentration camps in history, and Alfred Wetzler was one of the only prisoners known to have successfully broken out. Hiding for four days under a large stack of wood used for construction, Wetzler crawled under a fence when the guards were distracted and headed for Slovakia with plans and details about the camp. This information lead to an allied bombing run which saved the lives of 120,000 Jews.

Charles Victor Thompson was a death row inmate at Harris County Prison in Texas. He escaped using a fake id and pretended to be from the attorney general’s office. The deputies bought it, and he took off running. After 78 hours, officials found him at a liquor store, intoxicated.

Known for inspiring the movie Catch Me If You Can, Frank Abagnale got out of plenty of tricky situations in his lifetime. Once he was caught for fraud, he was taken to the Federal Detention Center in Atlanta. Because of heavy inspections during that time, he was mistaken for a prison inspector and used fake ids to help him prove his identity. Claiming he needed to meet up with his FBI contact, he left the building and called a taxi.

During the American Civil War, Libby Prison was where the Confederates kept Union soldiers in Virginia. Notorious for its overcrowding, the malnutrition of the inmates, and the mortality rate, Libby Prison was the last place a Union soldier wanted to go. With such poor conditions, 103 union soldiers worked together to escape by digging tunnels. After many failed attempts, they finally built a successful tunnel to get them out.

John Dillinger created plenty of trouble during Depression-era America, robbing 24 banks and breaking out of prison twice. While in prison the first time, he became an even better criminal, learning new techniques from inmates. When he got out on parole, he started robbing banks again but was eventually caught. His first prison escape happened when his gang impersonated police officers. When guards didn’t believe them, his gang shot the guards and released Dillinger. After robbing more banks, Dillinger was thrown back in prison, this time at Crown Point, Indiana. To escape, he fashioned a wood gun and threatened the guards with it. It actually worked; he got out again. Dillinger eventually died during an FBI raid.

Billy Hayes became a legend who wrote a famous book that turned into a famous movie, but in order to do that, he had to go through a whole lot of hell first. Caught drug smuggling in Turkey in 1970, his prison sentence wasn’t easy. He got life in a Turkish prison. The conditions were so awful it practically drove him insane. Over the years, he was moved from prison to prison, and his sentence was reduced from life to 30 years until he decided to escape in 1975. Afterward, he wrote the book Midnight Express.

Known as “Houdini Hinds,” Alfred Hinds was an escape artist, breaking out of three high-security prisons. Hinds used his high intelligence, extensive knowledge of the English legal system as well as prison security weaknesses to his advantage to continue breaking out. He was also successful in evading capture for long periods of time. Eventually, he figured out how to obtain a pardon using loopholes in the legal system.

Richard Matt and David Sweat were two inmates at the Clinton Correctional Facility, serving life in prison. Getting tools they used in the metal shop and seducing a prison employee to help them, they cut their way out of the prison. An extensive manhunt went underway afterward, resulting in Matt’s death and Sweat’s capture.

In 2008, America’s Most Wanted ran a feature on Sara Jo Pender, the only woman fugitive on their list at the time. She had been convicted of murder and escaped from Rockville Correctional Center using a prison guard as an accomplice. Being smuggled out of the prison, she fled to Northside Chicago and went under a different name. A rerun of America’s Most Wanted lead to her demise as a neighbor watched the episode and immediately called the police.

Ted Bundy was one of America’s most disturbing serial killers, but what some don’t know is he also was really good at escaping prison. During a preliminary hearing, he requested to represent himself. By doing that, he was allowed to not have shackles or handcuffs. Then, during a recess, he was granted access to the library to research a case, but instead, he opened a window and jumped out. He was a fugitive for six days before getting caught. His second escape attempt was much more methodical, involving a hacksaw, losing 35 pounds, and cutting a hole in his cell. While guards were celebrating Christmas, Bundy took the opportunity to break out. 17 hours later, prison guards realized Bundy had fled.

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A convicted killer serving 30 years, Pascal Payet has broken out of prison twice using not a hacksaw or fake ids but helicopters. The second time, he broke out in under five minutes with no violence. His break-out attempts have become the subject of the White Rabbit Project on Netflix.

During World War II, Colditz Castle was used as a military prison by the Nazis. Prisoners used every trick in the book to escape including tunnels, bed sheets as ropes, and smuggling out through trucks, but the most ingenious escape plan was the glider British soldiers built. Using materials around the prison, they constructed it to hold at least two men. All their hard word was wasted, though; it was never used as the war came to an end, and they were freed. But some speculate it was functioning and could have worked.

Richard Lee McNair had no intention of staying behind bars and came up with tons of ways to break out, including a time where he used lip balm to squeeze out of handcuffs or the other time he crawled through an air vent. His most audacious attempt was wrapping up his body as a package and mailing himself out of the prison. He’s now in one of the toughest maximum security prisons in America.

Brian Bo Larsen of Denmark escaped from prison an astounding 22 times. His methods are wide ranging, including sawing the bars off of windows or hiding out in trash cans. Sometimes it would take him only a day to escape, and other times an entire month, but he’d always escape and, of course, always be caught. Brian Bo Larsen is either the king of prison breaks or Denmark is just really bad at keeping him behind bars. Probably both.