10 Real-Life Prison Breaks That Will Blow Your Mind

By: Kevin Saltarelli
A man breaking out of a handcuff.
There have been some daring prison escapes all over the world. Chanin Wardkhian / Getty Images

Breaking out of a prison is no easy feat. Many prisons have security features such as CCTV, motion detectors, barred windows, massive walls, barbed wire, electric fencing, and armed guards. Despite these and other obstacles, some prisoners will exhaust the limits of their wit and ingenuity and take every opportunity they can to escape. Prison breaks have been a part of our pop culture since before the days of 19th century western outlaws. Like in Hollywood, it’s sometimes difficult to decide who the good guys are and who are the antagonists. Regardless, we all love a good chase.


10. Jack Sheppard

Jack Sheppard enjoyed near celebrity status in 18th century London for his multiple prison escapes. Though he apprenticed as a carpenter, in 1723 he decided that a life of crime was a more rewarding way to make a living. In 1724, he escaped from prison four times.

Sheppard escaped within three hours of his first arrest. He broke through the ceiling and lowered himself to the ground with a rope made from bed sheets. Three weeks later he was arrested again. This time he removed a bar from the window and performed the same bed sheet stunt. He was arrested a third time and sentenced to death. On the day of his execution, he loosened a bar from his window and escaped wearing women’s clothing. After his final capture, Sheppard was secured with 300 pounds of iron weights and placed under constant surveillance. He was executed on November 16, 1724.


9. “Houdini” Hinds

Alfred George Hinds was arrested for a jewelry robbery in 1953 and was sentenced to serve 12 years behind bars at England’s Nottingham Prison. Hinds, who protested his innocence, managed to escape the prison after sneaking through the locked doors and climbing over a 20-foot prison wall. He was arrested again six months later. Hinds filed a lawsuit claiming that the arrest was illegal and was granted a trial.

At the courthouse, Hinds had an accomplice smuggle in a padlock and install screw eyes into one of the washroom stalls. When two guards escorted Hinds to the washroom and removed his handcuffs, Hinds pushed the guards into the stall and locked them inside. He was captured at the airport five hours later and was sent to Chelmsford Prison. Within 12 months, Hinds escaped from Chelmsford. He was captured again two years later and served the remainder of his sentence.


8. The Biggest Prison Escape in British History

Her Majesty’s Prison Maze was considered to be one of the most escape-proof prisons in all of Europe. Each of the prison blocks were surrounded by 15-foot fences, 18-foot concrete walls, and solid steel gates that opened electronically. This Northern Ireland prison housed many Irish Republican Army prisoners that had been convicted of violent offenses.

On September 25, 1983, 38 IRA prisoners escaped from the Maze Prison. Shortly after 2:30 pm, the prisoners took control of their H-Block using guns that had been smuggled into the prison. At 3:25, a truck bringing food supplies was overpowered, the driver’s foot was tied to the clutch, and the driver was forced to drive out of the prison. Nineteen of the escapees were caught within several days of the escape. While some of the escapees were eventually found and extradited, those remaining have been given amnesties due to the politics in Northern Ireland.


7. Pascal Payet

In 1997, Pascal Payet participated in the robbery of a Banque de France armored vehicle, which resulted in the death of one of the guards. On October 12, 2001, he escaped from a prison on a hijacked helicopter. In 2003, he orchestrated the escape of three of his fellow accomplices with the help of another hijacked helicopter. He was eventually caught and sentenced to 30 years in prison for the 1997 murder, seven years for the 2003 escape and another six years for his own escape in 2001.

Payet became one of the most closely watched prisoners in France and was transferred to different prisons every few months. Despite these precautions, on July 14, 2007, four masked men hijacked another helicopter and facilitated the escape of Payet from a prison in Grasse. Two months later, he was captured again in Mataró, Spain. His current whereabouts are a well-kept secret.


6. Richard Matt and David Sweat

On June 6, 2015, Richard Matt, 48, and David Sweat, 34, escaped from the Clinton Correctional Facility in Dannemora, New York. Joyce Mitchell, a 51-year-old prison tailor shop worker, developed sexual relationships with both inmates, provided them with smuggled tools, asked them to kill her husband and planned to flee with the violent pair to Mexico.

Richard Matt and David Sweat used power tools to cut holes in the back of their adjacent cells, which led to a six story high catwalk that provided access to various pipes and tunnels. After cutting into a two-foot wide pipe, they travelled 400 feet inside the pipe and escaped through a manhole in the town of Dannemora. Joyce Mitchell, who had planned to rendezvous with the pair and provide a getaway vehicle, was nowhere to be found. Police killed Matt on June 26, and Sweat was captured two days later.


5. The Great Escape

Stalag Luft III was a German-run prisoner-of-war camp that housed captured air force personnel during World War II. Plans for the mass escape of hundreds of prisoners began in the spring of 1943. Three tunnels, codenamed “Tom,” “Dick,” and “Harry,” were dug 30 feet below the surface. Pumps were built to push fresh air into the tunnels. Lights connecting to the prison’s electrical grid were installed. The prisoners even installed a small rail car system to facilitate the digging process.

On the moonless night of March 24, 1944, 200 prisoners attempted to escape. Instead of leading to a nearby forest, the tunnel opened just short of the tree line and close to a guard tower. The 77th man through the tunnel was spotted by one of the guards and the escape was quickly foiled. Only three prisoners managed to escape. Fifty prisoners were killed and the rest were captured.


4. The Taliban Tunnel

In late 2010, the Mujahedeen began work on a 1000-foot tunnel in the city of Kandahar, with the hopes of freeing hundreds of Taliban insurgents. The tunnel, which took five months to dig, bypassed government buildings, watchtowers, barriers topped with razor wire, and went through the concrete floor of an Afghan prison. On April 25, 2011, 480 prisoners crawled to freedom in less than 30 minutes.

The Taliban had acquired keys prior to the escape, which were used to open the cells of their friends. On the other side of the tunnel, minibuses were waiting to drive the hundreds of escapees away from the heavily guarded area. It’s likely that some of the prison guards were either bribed or politically motivated to facilitate the escape. The only thing more remarkable than constructing a 1000-foot tunnel lined with a strong rubber ventilation tube is that nobody managed to stop it from happening.


3. Choi Gap-bok the “Korean Houdini”

Choi Gap-bok is a 53-year-old man, a criminal with over 20 years behind bars, and a yoga expert. Choi first escaped custody 25 years ago by slipping through the bars of a bus that was carrying prisoners to jail. He was captured two days later. Choi decided to practice yoga during most of his two decades in and out of jail. On September 17, 2012, he was ready to pull off an even more remarkable escape.

When the guards fell asleep he covered his pillows with a blanket, making it appear that he was still in bed, and applied skin ointment over his torso. He then squeezed through the tiny food slot at the bottom of his cell and escaped the prison. He was apprehended six days later and placed in a cell with an even tinier food slot. It seems that yoga, for some, isn’t just a popular way to exercise.


2. Sobibór the Nazi Germany Death Camp

During World War II, the Nazis would execute ten prisoners for every person who attempted to escape their extermination camps. By 1943, rumors had begun to circulate that the Nazis were intending to close the camps and exterminate all of their prisoners. Leon Feldhendler and Alexander Pechersky, prisoners at Sobibór, decided that being killed while trying to escape was better than being murdered in a gas chamber.

The plan was to have every prisoner attack at once, kill the SS officers and hope that the Ukrainian guards would retreat. On October 14, 1943, nine SS officers and two guards were isolated and killed. Unfortunately, a Ukrainian guard found one of the dead Germans and sounded the alarm. Around half of the 400 prisoners attempting to flee were shot and killed. The Germans then exterminated the remaining 300 prisoners and closed the camp. Only 58 of the escapees survived the war.


1. Frank Abagnale

Frank Abagnale is the notorious con man portrayed by Leonardo DiCaprio in the film Catch Me If You Can. Abagnale committing bank fraud and successfully impersonated pilots, lawyers, and doctors as a means of avoiding detection and inevitable imprisonment. In 1969, an Air France flight attendant recognized him and informed the police. He spent six months each in French and Swedish prisons before being extradited to America.

On arrival at the JFK airport, Abagnale escaped the plane and fled to Canada, but he was quickly apprehended. In 1971, Abagnale escaped a Federal Prison in Atlanta, Georgia. One of Abagnale’s friends supplied him with a fake prison inspector card and a forged FBI business card. He then convinced the guards that he was an undercover prison inspector who desperately needed to contact the FBI. Abagnale called his friend, walked out of the prison, got into a car and drove away.