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Top 10 Inmates Who Escaped From Prison Multiple Times

by Minnie Bundit
fact checked by Jamie Frater

Convicts serve their sentence for the crimes they commit by being incarcerated. We would like to think that prisons are sufficiently guarded and secure enough to make it impossible for prisoners to ever escape. And most of the time they are, but other times, inmates find unbelievable ways to make a break for freedom. In extreme cases, prisoners have escaped on multiple occasions. Here are ten of the best escape artists the prison system has ever seen.

10Pascal Payet

Pascal Payet, a French criminal convicted of murder, was well known for escaping prison Hollywood style—using a helicopter.[1]

In 2001, Payet escaped for the first time when he arranged for a helicopter to land on the prison roof and lift him to freedom. Two years later, while still on the run, he flew a hijacked chopper back to the prison to break out three of his friends. All four were captured three weeks later.

Payet was placed in solitary confinement and was shuffled from prison to prison to make planning an escape difficult, but despite this, he pulled off yet another daring jailbreak in 2007. This time, he used outside connections to hijack a helicopter, which was then redirected to a state penitentiary. Three men attacked the facility and escaped with Payet. However, he was caught three months later in Spain and has remained in custody ever since.

9Willie Sutton

Willie Sutton, also known as “The Actor” and “Slick Willie,” was considered one of the most notorious bank robbers in history.[2] He committed his brazen crimes in broad daylight by impersonating a policeman, messenger, postal officer, maintenance man, etc.

In 1931, Sutton was sentenced to 30 years in prison for assault and robbery. However, he escaped in 1932 by scaling the prison wall on two ladders. He spent two years on the run before being recaptured and sentenced to 25 to 50 years for a bank robbery.

Again he escaped, this time through a tunnel; he was caught the same day. Sutton was transferred to another facility and given life imprisonment as a fourth-time offender. In 1947, he escaped by dressing as a guard and became one of FBI’s most wanted fugitives.

He was arrested in 1952, sentenced to life imprisonment and an additional 105 years. However, he was released in 1969 due to ill health. He died 11 years later at the age of seventy-nine.

8Richard Lee McNair

carl bordelon interview of richard lee mcnair 05 april 2006

Richard Lee McNair was arrested in 1988 for killing one man and injuring another during an attempted robbery. He freed himself from the handcuffs by using his lip balm as a lubricant and escaped the police station. However, he was chased, recaptured, and incarcerated. He was given two life sentences plus thirty years for the crimes he committed.

In 1992, McNair escaped again by crawling through the prison’s ventilation ducts.[3] He eluded capture for ten months before he was found and sent to a federal prison. McNair was labeled a problem inmate, but even under the watchful eye of federal custody, he was able to execute a much more elaborate jailbreak.

In 2006, McNair used his job in the prison manufacturing area to craft himself an “escape pod,” complete with breathing tube. He hid the pod under a stack of mailbags and waited. The pallet of mailbags was shrink-wrapped and moved to a warehouse beyond the prison gates. McNair cut himself free and walked away.

Hours later, McNair was stopped and questioned by a police office taking part in the manhunt for the missing convict. The conversation was recorded on the patrol car’s dash camera, and even though McNair slipped up and gave two false names, the officer let him go.

McNair remained free for eighteen months until he finally surrendered during a chase in 2007. He was sent to a maximum security prison with almost no human interaction. He is still there to this day.

7Alfred George Hinds

Alfred George Hinds was an orphan who ran away from the children’s home when he was seven. He was arrested the first time for petty theft, but escaped from juvenile detention and joined the British army.

His next brush with the law occurred 1953 when he was arrested for jewelry theft and sentenced to 12 years in prison. However, he escaped two years later by opening a locked door and climbing a wall.[4] This earned him the nickname “Houdini” Hinds.

He spent 248 days as a fugitive before being arrested and sent to jail for the third time. While incarcerated, he filed a complaint against two officers. During the hearing, he managed to lock two police escorts in the toilet and escaped the courthouse on foot. However, he was caught five hours later at the airport.

About a year later, Hinds escaped once more and remained free for two years. He petitioned his legal case and publicized the story of his life which gained much attention from the public. He died in 1991.

6Yoshie Shiratori

Yoshie Shiratori was a Japanese man whose life story was immortalized in the famous Japanese novel, Hagok. In 1933, he was arrested on suspicion of murder and robbery and was facing a possible death sentence. However, he escaped in 1936 by picking the lock on his handcuffs by using a wire.[5]

Shiratori was recaptured twice more and successfully escaped on both accounts. In 1942 he climbed through a vent in the prison’s ceiling, and in 1944 he escaped by slipping out of his handcuffs.

In 1946, Shiratori was arrested a fourth time and received a death sentence. Awaiting his execution, he sawed through the floorboards of his cell with a piece of sheet metal, used a bowl to dig his way to freedom, and successfully escaped.

In 1948, he admitted to a police officer that he was an escaped convict. He was sent back to jail with a 20-year sentence but was paroled in 1961. Shiratori died of a heart attack in 1979 and became known as the man who escaped prison four times.

5Steven Jay Russell

In the early 90s, Steven Jay Russell was convicted of fraud and sentenced to six months in jail. However, after just four months, he simply walked out of prison by impersonating a guard.

Once he was caught and safely back behind bars, he soon managed to escape again. This time he impersonated a judge to reduce his own bail; he then fled to Florida. He was recaptured after only a week and was convicted of embezzlement and sentenced to 45 years.[6]

He escaped for the third time by impersonating a doctor and walking right out the front door, despite being under maximum security. Another 45 years was added to his sentence for this prison break.

Back behind bars, Russell took laxatives to lose a lot of weight and tampered with his medical records to claim that he had AIDS. He was sent to a hospital where he easily escaped. Shortly after, he sent a fake death certificate to the court, but the authorities didn’t buy it. He was convicted for the last time. He is now serving a 144-year sentence in solitary confinement.

4Moondyne Joe

Joseph Bolitho Johns, famously known as Moondyne Joe, was convicted of larceny in 1849. He was conditionally pardoned in 1855 but was arrested again in 1861 for horse theft.[7] He escaped while awaiting trial but was recaptured and served three years in jail.

In 1865, Joe was arrested once again for killing an ox. He made four escape attempts and was successful three of the times. He was put in solitary confinement, but even that did not stop Joe, and he escaped again in 1867. Inevitably, he ended up back in prison until he was granted early release in 1871. He died in the Fremantle Lunatic Asylum in 1900.

3Jack Sheppard

Jack Sheppard was a notorious thief and robber who was extremely popular amongst the poor. He was arrested for pickpocketing but escaped his cell by making a hole in the wall and removing iron and wooden bars from the window.

In 1724, Sheppard was sentenced to death for burglary. Once again, he escaped, but not for long. After being imprisoned, he managed to slip off his handcuffs and pick several locks.[8] He then used his blanket to slide off the roof and escape.

He was arrested two weeks later without a fight and was sentenced to death by hanging. Even facing the noose, Shephard had a plan; his accomplices would revive him after the crowd dispersed. Not surprisingly, that plan failed. After Sheppard’s death, his infamous escapes inspired many plays and novels.

2Nachman Farkash

Nachman Farkash was an Israeli boxer who turned his passion for sports to crime. In 1956, he was arrested for an armed robbery and was sent to jail. He escaped two years later but turned himself in shortly afterward.

He was arrested a couple more times for violence, break-ins, and theft, but he managed to escape from the jail every single time.[9] After four escapes, he was imprisoned once more and spent seven years locked up.

He decided to go back to boxing in 1969. In the following decade, he was arrested multiple times for violence and drug related crimes. By the end of the 70s, he gave up the crimes, married, and had children. He was found dead in 2014.

1Brian Bo Larsen

Brian Bo Larsen has the highest number of prison breaks with 22 successful escapes. Yes, 22. TWENTY-TWO! Larsen grew up with an abusive and alcoholic father. He started his life of crime at the age of eight with petty theft.[10] He robbed a gas station when he was 13 and was put in foster care.

Larsen started his long list of jailbreaks in 1989. He escaped prison a further fourteen times between 1990 and 2000. In one dramatic escape in 2000, Larsen stole a car and wrecked it during a police pursuit. Abandoning the vehicle, he continued on foot into a forest where a police dog eventually found him.

Multiple escapes later, in 2014, Larsen was on the run again. This time he was arrested after the police found him with prostitutes and with drugs in his possession. He broke out of jail for the 22nd time on December 13th, 2014, and became known as the “escape king.”

Larsen was finally tracked down; he was with a prostitute, and according to her, he was so high that he crashed through the fences and started fighting the air. However, by the time the police got there, he had already fled the scene. He was eventually located and arrested, fortunately.

Nobody knows whether 22 escapes will remain his record or if Larsen will manage to escape for the 23rd time. We’ll just have to wait and see.

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fact checked by Jamie Frater