List o’ Top Ten Jailbreaks and Prison Escapes

list of top ten jailbreak prison escapes“There isn’t a prison made that can hold me!” This line has been in dozens of movies and TV shows, usually said by a tough guy after he has been caught, tried and sentenced. While most jails and prisons are in fact highly secure and impenetrable, there have been some escapes that fall into the amazing category. Fake heads, fake guns, daring risks have all been used, and some have been made famous by highly successful movies. This list presents ten of the top jailbreaks and tells the stories behind them.

10. Pascal Payet

pascal payet caught and arrested

This “criminal who could not be held” escaped from jail using a helicopter, not once but three times. Late in 2001 Payet escaped with another inmate in a helicopter from Luynes prison in France. At the time of the escape he was awaiting trial for the murder committed during a armed robbery, when he shot a security guard 14 times. Still at large in 2003, Payet helped three other inmates break out of the same prison from which he had escaped. Again a helicopter was used in the escape. Payet was eventually recaptured and sentenced to seven years for having organized the 2003 breakout plus a six year sentence for his own 2001 escape.

Pascal Payet was freed with the help of four masked men who hijacked the aircraft and took the pilot hostage. They landed on the prison roof at the start of the night shift and used heavy machinery to break open two doors and enter the isolation ward where Payet was held. Authorities said he had been moved from one jail to another almost every three months because of his escape record. * full story here *

9. John Dillinger

Dillinger wanted poster

This daring jail escape was accomplished using a fake gun made of wood and shoe polish. A bank robber in America’s Midwest during the early 1930s, John Dillinger had robbed at least two dozen banks and four police stations and escaped from jail twice. He served time at the Indiana State Penitentiary at Michigan City, until 1933, when he was paroled. Within four months he was back in jail in Lima, Ohio. Dillinger had helped conceive a plan for the escape of himself and eight others he had met while previously in prison, most of whom worked in the prison laundry. Dillinger had friends smuggle rifles into their prison cells which they used to escape, killing two guards, four days after Dillinger’s capture. The group known as “The First Dillinger Gang” included Harry “Pete” Pierpont, Russell Clark, Charles Makley, Edward W. Shouse, Jr. of Terre Haute, Harry Copeland, James “Oklahoma Jack” Clark, John “Red” Hamilton and Dillinger’s mentor Walter Dietrich, a member of the Herman Lamm Gang . Three of the escapees arrived in Lima on October 12, where they impersonated Indiana State Police officers, claiming they had come to extradite Dillinger to Indiana. When the sheriff asked for their credentials, they shot him and beat him unconscious, then released Dillinger from his cell. The four men escaped back into Indiana where they joined the rest of the gang.

After this initial escape, and a spree of bank hold-ups, in 1934 Dillinger was again captured and again escaped. On March 3, 1934, Dillinger escaped from the “escape-proof” (as it was dubbed by local authorities at the time) Crown Point, Indiana county jail, which was guarded by many police officers and national guardsmen. Newspapers reported that Dillinger had escaped using a fake gun made from wood blackened with shoe polish. With his fake gun he was able to trick a guard into opening his cell. He then took two men hostage, rounded up all the guards in the jail, locked them in his cell, and fled.

8. George “Alfie” Hinds

prison cell block - prison escape george alfie hinds

Alfie Hinds under arrest following one of his three jail breaks, Portsmouth, 22 December 1960. Hinds was a petty criminal who was sentenced to 12 years for robbery, but used his IQ of 150 and an in-depth knowledge of law to gain legitimate freedom.

Mr Hinds escaped from jail three times, one of them by locking the guards in the bathroom. Alfie Hinds was a British man who managed to escape the law over and over again a total of three escapes. Four if you count his final, legal escape. Hinds came by his thievery honestly his dad actually died while being punished for armed robbery. In 1953, he was arrested for a major jewelry robbery $90,000 worth of which was never recovered. Although pleading not guilty, he was convicted and sentenced to 12 years imprisonment. Somehow he escaped through locked doors and over a 20-foot prison wall. The public started calling him Houdini Hinds.

He made an honest living as a builder and decorator across Europe until 1956, when Scotland Yard detectives tracked him down and arrested him again after 248 days as a fugitive. After his arrest, Hinds brought a lawsuit against authorities charging the prison commissioners with illegal arrest and successfully used the incident as a means to plan his next escape at the Law Court. When two guards escorted him to the bathroom and removed his handcuffs so he could take care of business, Alfie shoved them into the stall and locked it with a padlock (accomplices had installed screw eyes onto the door so he could do this). He was captured at the airport only a few hours later.

His third escape was from his Chelmsford Prison. He then returned to Ireland where he lived for two years as a used car dealer. His downfall came once again when he was pulled over for being in an unregistered car. This time, he used his smarts to find a loophole in the law at the time, prison escapes were not considered misdemeanors, so no time was added onto his original sentence. He finished out the six years from his jewelry theft sentence in 1953, won a libel suit against the arresting officer, and spent the rest of his life as a minor celebrity after selling his life story to the News of the World for a reported $40,000.

7. Julien Chautard

Julien Chautard prison escape

This man escaped from prison by clinging to the underside of the van that had just brought him there.

In 2009 French-born arsonist Julien Chautard pulled an audacious escape in which he succeeded in slipping away from a group of new arrivals at Pentonville prison in north London. As the other prisoners were being marched inside, Chautard managed to duck behind the prison van that had just brought them there from Snaresbrook crown court (where Chautard, 39, had been sent down for seven years). Chautard then succeeded in leaving the jail a few minutes later clinging to the underside of the same van. He later handed himself into police.

6. Frank Morris and Clarence and John Anglin

escape from alcatraz

This duo were the only prisoners to escape from thws infamous Alcatraz prison in California. During its 29 years of operation, the penitentiary claimed no prisoners had ever successfully escaped. 36 prisoners were involved in 14 attempts, two men trying twice; 23 were caught, six were shot and killed during their escape, and three were lost at sea and never found, although their bodies were never found.

But on June 11, 1962 Frank Morris, John Anglin and Clarence Anglin successfully carried out one of the most intricate escapes ever devised. Morris and the Anglins climbed up the ventilation shaft through one of the chimneys and reaching the top of the roof. The trio then climbed down the rooftop and paddled away on rubber rafts. The next morning police searched for the escapees on Alcatraz without success.

The acting warden said they put dummy heads – made of a mixture of soap, toilet paper and real hair – in their beds to fool prison officers making night-time inspections. Morris and the Anglin brothers subsequently disappeared without trace and are still wanted by the FBI, although they are believed to have drowned in San Francisco Bay while attempting to leave the island.

5. Billy Hayes


This American prisoner escaped from a Turkish prison and became a writer. Sentenced to 30 years in a Turkish jail for drug smuggling in 1970, the 22-year-old American was originally sentenced to four years and two months in a Turkish prison; with his release date weeks away, he learned that the authorities had chosen to penalize him with a life sentence, so he decided he had to escape. After six months of planning, he fought a prison guard, stole his uniform, and clutching $2,000 his father had smuggled into the prison in a photo album, he stole a rowboat, finally making it to shore. Hoping to reach Greece, Hayes dyed his blond hair black and began travelling towards the border. Barefoot, exhausted, and lacking a passport, he swam across a river and walked for miles. When he finally came upon an armed soldier, he thought that he had lost his bid for freedom, but the soldier yelled at him in Greek. Hayes eventually made it back to the U.S. safely and wrote an autobiographical book called Midnight Express, about his experiences in and escape from prison, which was eventually made into a hit movie.

Billy Hayes once commented on television after his “escape,” and he made a remark to the tune of “I like Turks — it’s their prisons I can’t stand.”

4. The Texas Seven


This wild bunch bunch escaped a maximum security prison using a highly elaborated scheme. On December 13, 2000, seven inmates at the John Connally Unit a maximum-security state prison in Karnes County, Texas escaped carrying out an elaborate scheme. Using several well-planned ploys, the seven convicts overpowered and restrained nine civilian maintenance supervisors, four correctional officers and three uninvolved inmates. The escape occurred during the slowest period of the day when there would be less surveillance of certain locations like the maintenance area during lunch and at count time. Most of these plans involved one of the offenders calling someone over, while another hit the unsuspecting person on the head from behind. Once the victim was subdued, the offenders would remove some of his clothing, tie him up, gag him and place him in an electrical room behind a locked door.

The attackers stole clothing, credit cards, and identification from their victims. The group also impersonated prison officers on the phone and created false stories to ward off suspicion from authorities.

After that, three of the group made their way to the back gate of the prison, some disguised in stolen civilian clothing. They pretended to be there to install video monitors. One guard at the gatehouse was subdued, and the trio raided the guard tower and stole numerous weapons. Meanwhile, the four offenders who stayed behind made calls to the prison tower guards to distract them. They then stole a prison maintenance pick-up truck, which they drove to the back gate of the prison, picked up their cohorts, and drove away from the prison.

A year later they were apprehended, as a direct result of the television show America’s Most Wanted.

3. The Rat Hell Prisoners

jailbreak in american civil war

This group is famous for the most famous, and successful, prison breaks made during the American Civil War. The Libby Prison Escape was one of the most famous (and successful) prison breaks during the American Civil War. Overnight between February 9 and February 10, 1864, more than 100 imprisoned Union soldiers broke out of their prisoner of war building at Libby Prison in Richmond, Virginia. Of the 109 escapees, 59 succeeded in reaching Union lines, 48 were recaptured, and 2 drowned in the nearby James River. The prisoners managed to tunnel through the prison’s basement to a nearby vacant lot. This was no easy task, as Libby’s basement was a dark and vermin-infested cellar known to the men as Rat Hell, but after seventeen days of digging, they reached a nearby tobacco shed. The officers escaped the prison in groups of two and three on the night of February 9, 1864. Once within the tobacco shed, the men collected inside the walled warehouse yard and simply strolled out the front gate. The tunnel provided enough distance from the prison to stealthily subvert those jurisdictional lines and allow prisoners to slip into the dark streets unchallenged.

The Libby Prison escape was possible thanks to the effort of its leaders, Colonel Rose and Major Hamilton. Rose and Hamilton worked tirelessly together to bring about the escape. It was Rose who thought of breaking into the basement from the chimney and Hamilton who engineered the passage. Rose toiled feverishly in the tunnel and organized digging teams while Hamilton worked out the logistics and invented contraptions for removing dirt and supplying oxygen to the tunnel.

2. Alfred Wetzler and Rudolf Vrba

Alfred Wetzler and Rudolf Vrba

This pair managed to escape from Auschwitz and later compiled a life saving report about the Nazi camp.

Wetzler was a Slovak Jew, and one of a very small number of Jews known to have escaped from the Auschwitz death camp during the Holocaust. Wetzler escaped with a fellow Jew named Rudolf Vrba. With the help of the camp underground, at 2 p.m. on Friday, April 7, 1944 the eve of Passover the two men climbed inside a hollowed-out hiding place in a wood pile that was being stored to build the Mexico section for the new arrivals. It was outside Birkenau’s barbed-wire inner perimeter, but inside an external perimeter the guards kept erected during the day. The other prisoners placed boards around the hollowed-out area to hide the men, and then sprinkled the area with pungent Russian tobacco soaked in gasoline to fool the guards’ dogs. The two remained in hiding for 4 nights to avoid recapture.

On April 10, wearing Dutch suits, overcoats, and boots they had taken from the camp, they made their way south, walking parallel to the So?a river, heading for the Polish border with Slovakia 80 miles (133 km.) away, guiding themselves using a page from a child’s atlas that Vrba had found in the warehouse.

Wetzler and Vrba later became known for the report that they compiled about the inner workings of the Auschwitz camp a ground plan of the camp, construction details of the gas chambers, crematoriums and, most convincingly, a label from a canister of Zyklon gas. The 32-page report was the first detailed report about Auschwitz to reach the West that the Allies regarded as credible. The report is said to have saved 120.000 lives.

1. Dieter Dengler

Dieter Dengler USN

Dengler became the only soldier to escape a prison camp during the Vietnam War. Dieter Dengler was a German-American Navy pilot who made a famous escape from a jungle prison camp during the Vietnam War. In early 1966, Dengler’s plane was shot down by anti-aircraft fire over Laos, and he was captured and shipped to a prison camp run by the Pathet Lao, a group of North Vietnamese sympathizers. Dengler had earned a reputation for his uncanny ability to escape from mock-POW camps during his military training, and he immediately contributed to a plan the prisoners had to make a getaway. On June 29, 1966, he and six other prisoners managed to escape from their hand and foot restraints and get a hold of the guard’s weapons. After gunning down three guards, Dengler escaped into the dense forest. He would eventually spend 23 days in the jungle enduring extreme heat, insects, leeches, parasites, and starvation before being rescued by an American helicopter. Only one of the other prisoners, a Thai contractor, survived the escape. The others were all either killed or disappeared in the jungle. Dengler would go on to become a successful test pilot in his later years, and to this day he is credited as the only American soldier to successfully escape from a prison camp during the Vietnam War.

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1 Response to "List o’ Top Ten Jailbreaks and Prison Escapes":

  1. pharmatech December 22, 2010 at 01:41

    Great site. A lot of useful information here. Im sending it to some friends!