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Unbelievable! The Craziest Prison Escapes Of All Time

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Here we present the craziest prison escapes of all time. Real-life prison escapes are even more intense than what we see in Hollywood movies, yet some prisoners are bold enough to manage multiple escapes.

Prison escapes may be a rare, but when they do occur they often cause scandal and gain lots of media attention.

We have compiled the top 15 prison escapes of all time and these are all real stories with fascinating outcomes.

1. El Cheeky Chapo

His ability to elude capture is the stuff of Mexican legend.

And in 2015, after spending a little over a year in prison following 13 years on the run, Joaquin “El Chapo” Guzman once again gave the slip to the long arm of the law.

In scenes reminiscent of The Shawshank Redeption, Guzman, the billionaire head of the powerful Sinaloa Cartel, fled via a mile long tunnel that ran from his cell to a building under construction outside the prison’s perimeter.

A massive manhunt was launched for the man known as Mexico’s Osama bin Laden, with flights grounded and roadblocks established.

Eighteen prison staff were also questioned in connection with his disappearance.

El Chapo was later caught again, after some time spent with Sean Penn, and is now back behind bars.

2. Escape from Alcatraz

Alcatraz Federal Penitentiary, a maximum-security prison that sits on a tiny island off the coast of San Francisco, was supposed to be the jail that no man could escape.

But three men tested that theory in June 1962 and gave birth to a great Hollywood film in the process.

Clarence Anglin, John Anglin and Frank Morris were serving time for a litany of crimes including bank robbery and car theft when they resolved to flee Alcatraz and its claustrophobic confines.

The trio cut holes in their cell walls, leaving behind dummy bodies in their beds to fool guards into thinking they were still incarcerated.

After exiting the building through a ventilation staff, the men scaled a prison fence and then made a raft from raincoats and contact cement.

They cast off into the cold waters of San Francisco Bay at around 10pm.

Parts of the raft and life preservers were later found in the bay along with some of the prisoners’ personal effects, leading investigators to conclude that the men had drowned.

The FBI officially closed the case on 31 December 1979, concluding that “no credible evidence emerged to suggest the men were still alive”.

However, no bodies were ever discovered.

And the 1979 film, Escape from Alcatraz appears to call that into question, strongly implying that the men reached the mainland.

3. Frank Abagnale

While we’re on the subject of Hollywood, no list of audacious prison breaks would be complete without a mention of Frank Abagnale, the international fraudster whose early life was retold in the 2002 film Catch Me If You Can.

Abagnale committed a series of jaw-dropping bold crimes, which included flying over 1,000,000 miles between the ages of 16 and 18 by impersonating a Pan Am cockpit.

The con man would ride in the spare seat of the cockpit – although he admits that on countless occasions he was left in charge of the plane while the pilot attended to a call of nature.

In his autobiography, Abagnale details his 1971 prison escape of equally intrepid nature.

After being sentenced to 12 years in prison in the US, Abagnale says he had the fortune of being transported to a detention facility by a Marshall who had forgotten his prisoner’s papers.

Abagnale seized upon the opportunity, persuading guards that he was actually an undercover prison inspector.

Authorities at the time often used the ploy to test their jails, and the guards duly swallowed the bait.

Abagnale writes that he was treated much better in prison than other inmates thanks to his ‘undercover’ status but the ploy really paid off once he’d enlisted the help of a friend, whom he calls in the book ‘Jean Sebring’.

Frank Abagnale with Leonardo Di Caprio who played his character in the Hollywood movie Catch Me If You Can

Sebring apparently doctored two business cards, one an FBI agent’s, the other a prison inspector’s and then smuggled them into the prison for Abagnale, who wasted little time in telling his guards that he needed to speak to the FBI agent.

The guards called the number on the agent’s card, Sebring picked up, told them that she needed to meet Abagnale outside the prison, and the con man walked straight out of the prison’s front door, presumably laughing all the way.

4. The key to freedom

In the 20th century, Parkhurst prison on the Isle of Wight was considered to be Britain’s answer to Alcatraz, but that didn’t deter three men from attempting a meticulously planned escape.

Keith Rose, Andrew Rodger and Matthew Williams were serving time for crimes that included murder and planting a bomb when, on January evening at the very start of 1995, they made use of a key they had cut themselves to flee the correctional facility.

Rose, Rodger and Williams used the key to open a series of doors, then cut through a mesh fence and scaled the perimeter wall.

They took a taxi to the town of Sandown, where they spent four days trying to steal planes and boats while sleeping rough in a field.

The three men were eventually discovered by an off-duty prison officer.

Parkhurst’s security level was downgraded in the aftermath of the escape attempt.

5. The Korean Houdini

Yoga practitioner, Choi Gap-bok provided the history books with a new take on prison escape methods.

Rather than bend his cell bars out of shape, he bent himself out of shape, slipping through the tiny slot at the bottom of the cell that’s used to give prisoners food.

The manoeuvre apparently took only 34 seconds in September 2012.

Gap-bok was rearrested six days later and placed in a cell with a much smaller food slot.

6. The life-saving escapee

Alfréd Wetzler’s escape from Nazi death camp Auschwitz is possibly the most important prison escape in history.

Wetzler, a Slovakian jew, escaped from Auschwitz with fellow inmate Rudolf Vrba in April 1944 by hiding in a wood pile that other inmates soaked with tobacco and gasoline to fool guard dogs.

After four nights hiding among the wood, the two men donned stolen suits and overcoats and began a 80 mile journey to the Polish border with Slovakia.

In his pockets, Wetzler carried a report on the inner workings of the death camp, including a ground plan, details of the gas chambers, and a label from a canister of Zyklon B, the gas that the Nazi’s used to kill millions of inmates.

It was the first detailed report about Auschwitz that the Allies regarded as credible, and led to the bombing of buildings that housed Nazi officials who dealt with the railway deportations.

About 120,000 Hungarian Jews are said to have been saved as a result.

7. The flying criminal

French murderer Pascal Payet has gained international notoriety for his role in a series of daring prison breaks that used helicopters as their modus operandi.

Payet’s first escape came in 2001, when he arranged for friends to collect him from the roof of a village prison in a helicopter.

Two years later, he orchestrated a rerun of the events to help three more prisoners escape the confines of the jail.

Payet was later caught and sentenced to 30 years in prison for murder in 2005.

Despite being one of France’s most closely watched prisoners, he managed to again break free of the law in 2007 by taking advantage of Bastille Day celebrations to jump into a hijacked helicopter flown by four masked men.

He was caught months later, near Barcelona, and transferred to a secret location, where he now remains.

8. Yoshie Shiratori

Yoshie Shiratori is best known for escaping from prison four times in three years.

After being convicted of murder, he was sentenced to life plus 23 years imprisonment.

Shiratori escaped from Aomori Prison in 1936, was recaptured and escaped from Akita Prison in 1942.

In 1944, he rusted his handcuff and an inspection hole with miso soup, before escaping from Abashiri prison.

He was caught again in 1946. Sapporo District Court sentenced him to death, which caused Shiratori to desperately find a way to escape and in 1947, he dug a tunnel and escaped for the fourth time!

In 1948, he was recaptured after admitting to a policeman that he was an escaped convict.

His death sentence was revoked and Shiratori eventually served 26 years before being paroled in 1961.

9. John Dillinger

John Herbert Dillinger Jr. was an American bank robber during the Depression-era who robbed two dozen banks and four police stations during his crime spree.

He escaped from prison twice in his criminal career.

During a period in jail in Indiana, Dillinger befriended a series of seasoned bank robbers who taught him to be a successful criminal.

After being released at the height of the Great Depression, Dillinger immediately returned to crime.

After robbing two banks, he was captured and imprisoned in Lima in the Autumn of 1933.

Dillinger used his time in jail to aid the escape of a group of inmates who he had met during his previous jail term.

Inmates smuggled guns into their prison cells, which they used to escape just four days after Dillinger had been captured.

The group then returned to the prison, impersonating Indiana State Prison officers and successfully released Dillinger from his cell.

After another series of bank robberies, Dillinger was captured again in 1934 and sent to Crown Point Jail. The police boasted to the media that the jail was escape proof.

This proved wildly untrue when Dillinger crafted a fake pistol from a piece of wood, supposedly using shelving in his cell and a razor to carve it.

Dillinger tricked a guard to open his cell and then took seventeen men hostage before luring the guards back to the cell block and locking them in his own prison cell.

He then fled.

Dillinger evaded police across four states before meeting his end on 22 July 1934 when a tip-off led to a shoot-out in Chicago. Dillinger was shot three times and was pronounced dead shortly after.

10. Alfred George Hinds

Alfred George Hinds was a British criminal who successfully broke out of three high security prisons while serving a 12 year prison sentence.

Hinds’ first escape was from a Nottingham prison in 1958 where he managed to get through locked doors and over a 20-foot prison wall to his freedom.

This feat earned him the name ‘Houdini Hinds’ in the media.

He travelled throughout Europe during his time on the run, working as a painter-decorator before being apprehended after 248 days of freedom.

Hinds used his re-arrest to his advantage, bringing a lawsuit against the authorities and hence finding a reason to be escorted to the Law Courts.

Accomplices supplied Hinds with a padlock and attached screw eyes onto a toilet cubicle so that while being escorted to the toilet, Hinds bundled the two guards into the cubicle and locked them in.

Escaping onto Fleet Street, Hinds made for the airport where he was captured five hours later.

Hinds’ third and final prison escape came less than a year later, when he escaped from Chelmsford Prison.

He fled to Ireland where he lived for two years under an assumed name before being stopped driving an unregistered car and rearrested.

Following his eventual release from Parkhurst Prison, Hinds became a member of Mensa.

11. Texas Seven

A group of prisoners, dubbed the Texas Seven escaped from the John B. Connally Unit on 13 December 2000.

An elaborate scheme devised by the group led to the group overpowering and restraining 16 people, including supervisors, officers and three uninvolved inmates.

Once overpowered, clothing, credit cards and ID were taken from the victims and used to impersonate civilians at the back gate of the prison.

Four of the offenders stayed behind to make phone calls to the prison tower guards to distract them.

The rest raided the guard tower and stole numerous weapons and then stole a prison maintenance pick-up truck in which all seven drove away from the prison.

They were apprehended just over a month after.

Six of the seven were placed on Texas’ Death Row while the seventh (Larry James Harper) committed suicide rather than return to prison

12. Ronnie Biggs

Ronald Arthur Biggs, more commonly known as Ronnie Biggs, is infamous for his role in the Great Train Robbery of 1963, and for his 36 years living as a fugitive until his voluntary ‘surrender’ in 2001.

Initially captured and sent to prison for his part in the Great Train Robbery, Biggs only served 19 months of his prison sentence before escaping from Wandsworth Prison on 8 July 1965 by scaling a wall with a rope ladder and dropping on to a waiting van.

He fled to Brussels via boat and then onto Paris where he acquired a new identity and underwent plastic surgery.

His 36 years on the run were spent predominantly in Australia and Brazil.

On 7 May 2001, Ronnie voluntarily returned to the UK and was immediately arrested and imprisoned.

He served 8 years in jail before being released on compassionate grounds in 2009. He died in December 2013.

13. Maze Prison

HM Prison Maze was the location of the biggest prison escape in British history, when on 25 September 1983, 38 IRA prisoners smashed their way out of the maximum security prison, widely considered to be one of the most escape-proof prisons in Europe.

Fifteen foot fences and Eighteen foot thick concrete walls topped with barbed wire encircled H-Block, and solid steel doors barred all exits from the prison complex.

Prisoners planned the escape over several months. Two accomplices, Bobby Storey and Gerry Kelly, started work as orderlies to identify weaknesses in the system and six handguns were smuggled into the prison by exploiting these downfalls.

Just after 2.30pm, prisoners seized control by simultaneously taking the prison officers hostage, and hijacking a lorry which was delivering food to the block.

Officers in the gatehouse were also taken hostage and after several attempts, the main gate was opened.

Abandoning the lorry after a makeshift road block was set up by two cars just outside the prison, the prisoners escaped over a fence.

The prison was made secure by 4.18pm minus 38 prisoners. Twenty prison officers were injured and one died after suffering a heart attack during the escape.

14. The Great Escape

Devised by Squadron Leader Roger Bushell in the Spring of 1943, the ‘Great Escape’ from prisoner of war camp Stalag Luft III occurred on the night of 24 March 1944.

Bushell was in command of the Escape Committee in the North compound, where the British airmen were housed.

His ‘Great Escape’ plan involved the building of three “bloody deep, bloody long tunnels” underneath the camp fences.

The tunnels were nicknamed Tom, Dick and Harry. If one of the tunnels was discovered by the Germans, it was presumed that they would never suspect two more tunnels might be underway.

More than 600 prisoners were involved in the tunnels’ construction, with Bushell aiming to get 200 prisoners to freedom.

The tunnels descended 30 feet below the surface and were only 2-foot square. The walls were shored up with pieces of wood which were mainly scavenged from the prisoners’ beds.

The 200 potential escapees were divided into two groups.

The first group of 100, called “serial offenders”, were guaranteed a place and included prisoners who spoke German well or had a history of escapes, with 70 of them chosen because they were considered to have contributed most to the tunnels.

The second group was chosen by drawing lots.

On Friday 24 March, at 10.30pm, the first man out emerged and discovered the tunnel had come up short.

Rather than reaching into a nearby forest, the tunnel came out just short of the tree line and perilously close to a guard tower.

Even so, 76 men crawled through the tunnel to freedom before the 77th was spotted by the guards at 4.55am on 25th March.

Of 76 initial escapees, 73 were recaptured.

Adolf Hitler order half of the escapees to be executed as an example.

15. Pretoria Prison break

Locked up in a maximum-security jail for setting off harmless leaflet propaganda bombs and spreading dissent against the apartheid regime in 1970s South Africa, Stephen Lee and friend Tim Jenkin embarked on one of the most audacious prison breaks in history.

On arrival at Pretoria, a jail for white political prisoners, both men were so focused on escaping they even asked relatives to smuggle in money for taxi fares once they broke out.

Lying on his bunk one night, Tim gazed at the lock in front of him and had a flash of inspiration.

At first the wooden key didn’t turn the inner cell door lock.

Fortunately marks on the wood showed where the key was jamming, so Tim knew which parts to file down. After filing and filing, he tried again.

Using an ingenious homemade wooden key attached, like a crankshaft, to the end of a broomstick, Tim had just got through his outer cell door.

But as Stephen would soon find out on a vital reconnaissance trip to the dentist, there were still a total of 10 doors separating them from freedom.

Over a long series of dummy runs that took over a year to complete, they got as far as door 10, the door to the outside.

Unwilling to take any more risks, they had to leave this final barrier untested until the night of the actual escape.

When the night came, on December 11, 1979, 18 months after their conviction, Denis Goldberg, a political prisoner who would serve 22 years, distracted the guards.

It was not until the following morning that the warders realised that three men were missing.

A massive police operation was launched to recapture the convicts, but by that time Stephen, Tim and another prisoner, Alex Moumbaris were on their way out of South Africa.

Sources: Oxford Castle & Prison,,

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