Prisoners Who've Escaped Jail A Surprising Amount Of Times

Humanity has struggled with how to deal with criminals throughout its history. Society has been imprisoning people for almost as long as we've had society, but dumping folks in prison was originally not considered punishment — it was just a way to make sure criminals stayed around to receive punishment. In other words, prison was really just a waiting room on the way to execution, corporal punishment, or something else. When executions became increasingly rare in the 18th century, prison became the chief way to actually punish criminals, eventually leading to the modern prison system.

One thing is certain: For almost as long as people have been sent to prison, people have been escaping from prison. And for almost as long, we've been fascinated by prison escapes. No matter how terrible the people involved might be, the idea of figuring out a way to leave a place specifically designed to stop you from leaving is simply a great story — from "The Count of Monte Cristo" to "The Shawshank Redemption", we love a good prison escape story.

The reason is obvious: Managing to break out of prison is cool. It requires incredible luck, skill, or both, seasoned with a generous amount of "Sticking It to The Man." Doing it once? Impressive. Doing it multiple times? Absolutely mind-blowing. Here's a list of prisoners who've escaped jail a surprising amount of times.

Ted Bundy was one of the most terrifying people of all time because of his ability to appear totally normal — even charming. According to Britannica, Bundy sexually assaulted and murdered at least 28 women, and possibly many more. Despite the grievous nature of his crimes, Bundy was able to escape from prison twice — and came very close to a third attempt.

As reported by Bustle, Bundy was caught with maps and other documents suggesting he was planning an escape in Utah in 1976, and was placed in solitary confinement before he could put his plan into action. He was extradited to Aspen to stand trial for the murder of Caryn Campbell in 1977. Since he was assisting in his own defense, Bundy was permitted access to the law library at the Pitkin County Courthouse — unshackled, which meant he wasn't restrained in any way. One day, when his guard stepped outside for a smoke, Bundy simply jumped out a window, spraining his ankle. Bundy fled and sheltered in a cabin for six days, then hobbled back to Aspen, tried to steal a car, and was recaptured.

According to Yahoo!, Bundy escaped from prison again a few months later — but this time it wasn't an impulsive decision. Noticing a gap in the ceiling of his cell, he stopped eating in order to lose enough weight to fit through it, stole a set of clothes from a guard, and simply walked out of prison. He managed to stay free for the next two months before being recaptured.

You might think you're good at things, but there is no way you will ever be as good at breaking out of prison as Brian Bo Larsen. According to Yahoo!, Larsen, who hails from Denmark, broke out of prison an absolutely incredible 22 times.

IceNews reports that the "jailbreak king" has used many different tricks to get out of various prisons. In 1995 he simply took advantage of good luck, when a truck crashed into a prison's wall and created a big hole that Larsen simply walked through, along with 11 other inmates. In 2004, he was working raking up leaves and dumping them in a container. Just before the container was set to be taken out of the prison for disposal, he jumped in and hid. And in 2014, while serving a seven-year sentence for armed robbery, Larsen really went old-school by sawing off the bars of his cell and using a rope ladder, which seems like something out of a movie — although the police in Copenhagen described the escape as "risky" due to the height involved.

The Straits Times reports that Larsen didn't stay free for long: He got really high on drugs, stole a car, and crashed it, which led to his recapture.

According to The Vintage News, Moondyne Joe was born Joseph Bolitho Johns in Wales in 1826 and worked as a copper miner until he was arrested for theft in 1848, when he was 22. He was sentenced to 10 years of penal servitude and promptly shipped off to Australia.

When he arrived in Western Australia, he was granted his freedom. He moved into an area called Moondyne by the local Aboriginal tribe and from there gained his nickname, but according to 9News he was arrested for stealing a horse in 1861. He escaped his first jail cell in the middle of the night — and even stole the horse a second time — but was recaptured the next day and sentenced to three years, although he was released early due to good behavior.

He was arrested four more times in the next ten years, and escaped three times in a row, once from an "escape-proof" cell constructed especially for him. After his fourth arrest the local governor simply set him free, probably thinking it was too much trouble trying to hold him. According to author Graham Seal in his book "Folk Heroes and Heroines Around the World," Moondyne Joe's exploits were so famous he became an Australian folk hero.

Incredibly, when Joe was found wandering in his old age, he was sent to an old-age home — and promptly escaped from it three times, earning himself one final prison sentence.

The Los Angeles Times reports that Richard Lee McNair was arrested in 1987 for murder and sentenced to life in prison. Since his conviction, he has escaped from prison three times in pretty spectacular fashion.

While sitting in a police station just a few months after his conviction, he used lip balm to grease his hand and slip it through the handcuffs he was wearing. He made a run for it but found himself on the third floor of a nearby building — he jumped, but was recaptured.

A few years later, McNair wriggled through a ventilation duct to escape North Dakota State Penitentiary, and managed to remain free for nine months before he was recaptured. But it was his third escape that crowned him a true legend in the escaping "business." McNair was sent to a supposedly inescapable maximum security prison in Pollock, Louisiana. As author Cameron K. Lindsay notes in his book "Triple Deuces," all inmates at Pollock were required to have a job, and McNair worked in a factory that shipped a lot of orders. In 2006, McNair created a hiding space on a shipping pallet under a stack of mailbags, used a breathing tube, and essentially shipped himself out of the prison. Incredibly, McNair was stopped by police almost immediately — but was set free because he didn't seem to match the photo the officer was given. McNair managed to stay free for over a year.

As noted by Britannica, Jack Sheppard grew up rough. His father died when he was young, his education was minimal, and he fell in with thieves and sex workers as a young man. This led to a legendary life of crime that included four prison escapes of increasing difficulty and awesomeness.

As Historic UK explains, Sheppard was an enthusiastic criminal and drunkard. In 1723, he was arrested for picking pockets and sent to New Prison in Clerkenwell. Sheppard proceeded to file off his chains and window bars, and made a rope from sheets and blankets. In 1724, Sheppard was sentenced to death in Newgate prison, but once again filed down bars in his window and climbed out to freedom while some friends distracted the guards.

According to BBC Radio 4 Sheppard's next escape involved using a woman's dress as a rope — and then putting the dress on and walking away disguised as a woman. His final escape was his most famous. Once again in Newgate Prison, he slipped out of handcuffs and a chain and made his way through several doors and up onto the roof. He then went back to his cell to get a blanket and used it to slide down the roof. Sadly that was it for his career and his life: He was recaptured and hung in 1724, when he was just 22 years old.

If you're going to go through the trouble of escaping from prison, you might as well do it as spectacularly as possible. At least that's apparently what French supercriminal Pascal Payet believes.

According to author Paul Buck in his book "Prison Break," Payet was sentenced to 30 years in prison for a murder he committed during a bank robbery in 1997. In 2001, according to "TIME-LIFE Great Prison Escapes", Payet got some friends to fly a helicopter to the prison and pick him up off of the roof, as one does. Incredibly, Payet remained free for years — and even arranged to have a helicopter fly over to the same prison and help some of his friends escape.

Payet was eventually recaptured, and the authorities began moving him every few months and keeping him under surveillance. But according to Time, it didn't matter — in 2007, friends of his hijacked a helicopter (yes, again), flew it to the penitentiary and forced their way inside with guns. They retrieved Payet and flew off with him — according to ABC News the whole prison break took five minutes. He managed to stay out of prison for three more months, before being recaptured in Spain.

When you're serving 144 years in prison, it's understandable that you might put a lot of energy into figuring out how to escape. As reported by The Daily Beast, Steven Jay Russel became very, very good at escaping from prison — over a five-year period, Russell escaped four times from different prisons in Texas. That's impressive enough, but it was the flair and drama that Russell brought to his escapes that made him truly remarkable. According to The Guardian, in 1993 he broke out of Harris County Jail by stealing some women's clothes as well as a walkie-talkie and pretending to be a worker. In 1996, he squeezed the ink from green felt-tip pens he stole from prison art classes and dyed his prison overalls green to look like surgical scrubs — and pretended to be a doctor. When he was recaptured, he began to feign illness, using laxatives and faking medical records to get himself transferred to a nursing home. From there, he then posed as his own doctor on the phone to have himself declared dead.

All of this showmanship brought Hollywood calling. As Russell himself detailed in HuffPost, in 2010 the film "I Love You, Philip Morris," based on his life and prison escape exploits and starring Jim Carrey and Ewan McGregor, was released, making Russell one of the most successful prison break artists in more ways than one.

When your crime career earns you the nickname "Pretty Boy Floyd," your life is not going in the right direction. Michael Floyd Wilson is the perfect example of this general rule: Sentenced to two life sentences after being convicted of two murders and several other crimes in 2015 according to CBS News, he's done his best to get out of prison ever since. And he's succeeded no fewer than three times.

The first wasn't so impressive: Back in 2001 Wilson escaped from a county jail — not exactly the epitome of security — while being held on a burglary charge. But after his murder convictions, Wilson stepped up his game. According to WLOX, in 2018 Wilson escaped from Stone County Correctional Institute in Mississippi by simply climbing over a fence and hoofing it. The escape sparked a three-day manhunt that tracked him down about 70 miles away.

Wilson was charged with the escape and had time added to his sentence — and the judge classified him as a "habitual offender." The extra security didn't stop him from climbing yet another fence in February 2022, however, according to The New York Post. Wilson escaped the Central Mississippi Correctional Facility, suffered severe cuts from razor wire, and somehow managed to be treated at a local hospital — twice! Wilson was eventually recaptured when his stolen car ran out of gas.

John Dillinger is one of the most famous American criminals in history. As noted by Britannica, he's known as a bank robber who committed a series of crimes across the country between 1933 and 1934 as the Great Depression smothered the country.

But Dillinger is just as famous for his two prison escapes, which is generally two more than most people manage. Dillinger was first arrested in September 1933 and thrown into an Ohio jail — but five of his friends, who Dillinger himself had previously helped escape prison, returned the favor, killing a local sheriff in the process.

But it was his escape in 1934 that made him legendary. As reported by Time, Dillinger had been arrested in January and charged with armed robbery and murder of a police officer in Indiana, where he was taken to await trial. As noted by The History Reader, the second floor of the Lake County Jail was considered to be "escape-proof" by standards of the time, but Dillinger made a mockery of the concept. Dillinger began a habit of whittling a piece of wood — and eventually carved a realistic-looking gun, which he used to bluff his way out of prison, aided by at least one guard who fell asleep at his desk. He then stole the sheriff's car and drove off with an automatic rifle stolen from the cops.

Willie Sutton was the kind of bank robber you want to be. Using convincing disguises and an ability as an actor, Sutton posed as policemen, messengers, and maintenance workers as he merrily robbed banks — Britannica reports that Sutton himself estimates he stole about $2 million from banks over the course of his career.

He was also known for some pretty brazen and surprisingly common prison escapes. The FBI reports that Sutton was sentenced to 30 years in prison for assault and robbery in 1931, but escaped from prison a little more than a year later, by attaching two ladders to each other to create one long enough to scale the prison walls. He stayed free for nearly two years, but was eventually apprehended and received an additional 30 years on his sentence.

Sent to Eastern State Penitentiary, Sutton was held for the next 11 years before escaping with a group of fellow inmates in 1945. As Smithsonian Magazine details, Sutton made at least five escape attempts before he and his compatriots used spoons and flattened cans to dig a tunnel over the course of months. Sutton was recaptured the same day and was sentenced to life in Philadelphia County Prison. Two years later, Sutton and some other prisoners dressed up as guards and escaped again — the searchlights actually caught him in the act of putting a ladder against the wall, but his uniform convinced the other guards that everything was okay.

When your nickname is Alfie and you wear glasses so thick you might be able to see the future, you're not a candidate for "Coolest Criminal." And yet Alfred "Alfie" George Hinds was an accomplished safecracker and thief, as well as a consummate prison escapee.

The Vintage News reports that Alfie grew up in a harsh orphanage, driving him to run away at the age of seven and turn to thievery to support himself. According to "TIME-LIFE Great Prison Escapes", when Alfie was arrested and convicted of robbery in 1953 and sentenced to 12 years in prison he freely admitted he was a thief, but vigorously denied committing that particular crime. His sense of injustice convinced him he had to escape in order to prove himself innocent. Two years into his sentence, he managed to slip past a normally locked door, climbed the fence, and was gone.

He managed it twice more. Eight months later, Hinds was recaptured in 1956 and sent back to prison. According to Time, he filed a lawsuit against the arresting officers, and, when he was taken to court, he managed to lock his guards in a bathroom and flee. He was recaptured five hours later and sent back to prison — and escaped for the third time a year later. He managed to remained a free man for two years, and was only caught because he drove a car with an expired registration.

As reported by The New York Times, Mark DeFriest's story is a tragedy: When he was 19 years old, his father passed away and left him his tools in his will. But DeFriest took the tools before the will had been processed, and he was arrested for theft. If he'd served his time, he would have been free in a few years. Instead, he attempted escape a remarkable 13 times, succeeding seven times and adding many more years to his sentence.

As noted by CBS News, DeFriest also made things worse for himself by accumulating hundreds of disciplinary complaints while a prisoner, which many believe can be attributed to undiagnosed autism — or genius. For his multiple escape attempts and better than 50% success rate, DeFriest is known as the "Prison Houdini" — and The Washington Post reports that even the corrections officers that guarded him referred to him as an "escape artist."

And his escapes were brilliant. In one, he dosed the prison staff with LSD and escaped while everyone was freaking out. In another, he crafted wooden "zip guns" in the prison's workshop, then pulled one of his own teeth in order to prompt a visit to the dentist. But each of his 13 attempts cost him in terms of more prison time. According to The Bitter Southerner, he was finally granted parole in 2019 after serving a cumulative 39 years of his life behind bars for stealing his own tools.