12 Craziest Prison Escapes of all Time

Correctional officers protect society by guarding those that need to be locked up. On rare occasions, those inmates use their skills and cunning to escape. Correctional department authorities are prepared to address the usual escape attempts – smuggling of contraband, blackmail, and bribes. However, it’s the use of fruit, yoga and helicopters that they were never trained for. We have compiled a list of the 12 craziest international prison escapes of all time. These inmates really thought outside of the box.

Public Enemy #1 – March 3, 1934

We must start with the man who’s crimes earned him the infamous title “Public Enemy #1” by the FBI. Gangster John Dillinger, who was both a bank robber and a murderer, escaped jail twice. His initial escape was from a jail in Ohio with the help of eight of his friends. During his second capture, he was taken to Lake County Jail in Crown Point, where Lake County Jail officials described the prison as “escape proof.” However, in what is now a famous tale, Dillinger escaped from the jail with a fake gun . There is still debate about what exactly the gun was made from, and how the escape happened, but popular opinion is that he used a wooden gun painted black with shoe polish. Guards were fooled by the gun and allowed Dillinger to leave the prison.

While on the run he made the most of his time and got a few more robberies under his belt before being killed in a shootout with the FBI a few months later in July.


The Alcatraz Escape – June 11, 1962

In another extraordinary tale that has been popularized by a blockbuster film starring Clint Eastwood, three prisoners escaped Alcatraz. Alcatraz was a maximum-security federal prison located on an island off the coast of San Francisco. Surrounded by water, it was deemed to be inescapable. That all changed on June 11, 1962 when Frank Lee Morris, John Anglin, and Clarence Anglin escaped  by digging a tunnel through a concrete wall using a spoon. To buy time, they created paper mâché dummies outfitted with hair from the prison’s barber shop and lay the decoys in their beds. The prisoners then went into the water via a boat they had made from over 50 stolen raincoats.

Their escape was not noticed by prison guards until the next morning. At that time a search began but ultimately the men were never heard from again. The FBI and Alcatraz jail officials assume, to this date, that the three men drowned in the water. If this theory is true, their bodies have never been discovered.

There has been some speculation that the three men escaped and moved to Brazil. A letter was submitted to the police in 2013 claiming to be from John Anglin. It claimed that while all three successfully escaped, he was the only remaining one still alive at the age of 83.  The FBI stated that fingerprint and DNA evidence was inconclusive, and the authenticity of the letter could not be positively concluded. In 2016 a photo was revealed that allegedly showed the two brothers in Brazil 13 years after their disappearance. Authorities have not confirmed that this photo is in fact the escaped convicts.

Image Source: History.com

Catch Me If You Can – April 1971

In another now-turned-Hollywood-classic, the escape of Frank Abagnale has been heavily popularized. Frank was a notorious fraudster and imposter, on who the movie ‘Catch Me If You Can’ is based on. Frank started committing crimes as young as 15, and escaped prison twice. The first time while he was being deported to the US; Frank escaped off a British airplane at JFK. He was eventually recaptured in April 1971, at which point he made his more grandiose escape.

In April 1971, Frank used his wits to trick the guards into aiding in his escape. When checking into the prison, the US Marshal forgot Frank’s detention commitment papers. At this time in the US, many prisons were being inspected by federal workers for civil right issues. Frank seized the opportunity to manipulate the prison guards into believing he was an undercover inspector posing as a prisoner for a review. He spent weeks building up the story. He used an accomplice on the outside to further convince the guards by forging a fake FBI business card that identified him as an officer.

The guards gave him special treatment thinking that they were helping the prison pass the inspection with flying colors. Eventually, he walked right out the prison and the guards allowed it, thinking they had fooled Frank.

He was on the run for another two months before being re-arrested. However, the PR damage was done and the story got out making Frank an instant sensation for his ingenious escape.

Image Source: Toshi Times

Nectarines are the Key – May 1986


In 1986, Michel Vaujour and his wife used fruits in an elaborate escape plan. Michel’s wife, Nadine, took helicopter lessons prior to the escape. Michel used nectarines that were painted like grenades to force his way onto the roof of the prison. From there, his wife picked him up in a helicopter and they landed in a football field. His wife was caught and arrested, and Michel was shot (and survived) after a failed robbery attempt.

We can’t help but wish we had a picture of those realistic looking nectarine grenades. Michel may have missed his calling as an artist!

The Magic Key – January 10, 1995

In an escape that sounds unbelievable, three inmates escaped in the UK by memorizing the outline of a key. Inmates Andrew Rodger, Keith Rose, and Matthew Williams worked in the prison’s sheet metal shop and made all the necessary tools for their escape in the shop. They memorized a guard’s master key outline and made a replica that essentially allowed them to open any door during their escape. They also made a 25-foot steel ladder and a “homemade” gun.

They were caught 4 days later, trying to map out a plan to steal a plane.

Not One, Not Two, But Three Helicopter Escapes – October 12, 2001

French robber and convicted murderer Pascal Payet has three successful prison escapes under his belt that have made him internationally renown. On October 12, 2001, Pascal escaped a French village prison by having his friends collect him from the roof of the prison with a hijacked helicopter.

He then returned to the prison via helicopter in 2003 and helped three more prisoners escape.

In 2005 he was sentenced to 30 years for the murder of a guard that occurred during a car hijacking in 1997. He was only in jail for a short time before he decided to escape again. In July 2007, Pascal arranged for his friends to hijack a helicopter, take the pilot hostage and force him to fly to Pascal’s prison where he was waiting on the roof. While his third escape was successful, he was eventually recaptured in Spain.

Mexican Drug Lords Don’t Build Their Own Tunnels – January 2001

Joaquín Guzmán Loera, also known as ‘El Chapo’, is a Mexican drug lord and former leader of the Sinaloa Cartel. He has managed to escape from prison twice. His first escape occurred in January 2001. After being arrested on drug charges by the Mexican police, El Chapo bribed guards in his prison to assist him in his escape. He escaped the prison by climbing into a laundry cart and was able to avoid capture for the next 13 years.

In 2014 he was rearrested and a short 17 months later, El Chapo escaped again. This time, gaining a lot of media attention, Chapo escaped through a mile-long tunnel built underneath the showers of the maximum-security prison. This wasn’t your run-of-the-mill tunnel, it had lighting, ventilation and a modified motorcycle on tracks that was probably used to aid in the construction of the tunnel. He was recaptured again January 2016 and presently remains in jail.

That’s A Bit of a Stretch – September 2012

South Korean Choi Gap Bok was arrested on September 12, 2012 for robbery charges. Choi was a yoga practitioner of 23 years and on September 17th, just five days after his arrest, he squeezed through a food slot that was only 5.9 inches tall and 17.7 inches wide. The entire movement reportedly took 34 seconds.  His escape earned him the nickname of the “Korean Houdini” from journalists, but he was caught just six days later.

Image Source: Daily Hunt

Now That’s a Happy Meal – June 5, 2015

David Sweat and Richard Matt, two prisoners at the Clinton Correctional Facility, spent months planning their scape. Both inmates worked in “privileged” sections on the prison, including the kitchen, which gave them access to tools. When they walked around the prison field, the duo realized that a speed bump in the field was actually a pipe that they could crawl through to escape. Richard Matt also established a relationship with the prison tailor, Joyce Mitchell, and convinced her to sneak in hacksaw blades hidden in frozen hamburger meat.

All of this allowed them to have the necessary tools to cut through steel walls. They left dummies with Clinton Correctional Facility sweaters in their beds to fool guards during their nightly check. They also reportedly left a note that said, “Have a nice day.”

Originally, Joyce was supposed to meet them outside of the prison walls and further aid their escape with a getaway vehicle. However, Joyce failed to turn up and the pair had to continue on their way. After several days on the run from officials, the two were eventually located and a standoff resulted in Sweat being wounded and captured, and Matt being shot dead.

“The married 51-year-old told [New York Inspector General Catherine Leahy Scott] that she ‘enjoyed the attention, the feeling both of them gave me,’ but that she only had a physical relationship with Matt.”  – Oxygen.com

Joyce Mitchell plead guilty to her involvement in the escape and was sentenced to a maximum of 7 years in prison. She is serving her time at Bedford Hills Correctional Facility for women and has been denied parole twice so far.

A Woman’s Touch – 2012

In 2012, Ronald Silva, a drug trafficker, escaped from a Brazilian prison. When his wife came for her weekly visit, she gave her husband the clothes she was wearing and changed into a spare outfit she had in her purse.

Silva then went to great lengths to shave his arms and legs, apply fake nails, put on a wig, lipstick, heels, and the outfit that his wife had left him. He was able to walk right past the guards and out onto the street without attracting any attention. However, as he walked towards his friends waiting at a bus stop, a clever cop noticed him struggling to walk in the heels and spotted that something was not quite right.

Silva’s wife claimed that while she brought him the clothes, she had no idea what he intended to do with them.

Image Source: Mirror.com 

You Butter Believe This One – July 2017

In July 2017, twelve inmates escaped a jail in Alabama from the Walker County Jail. The prisoners smeared peanut butter over a door’s signage. The signage indicated that the door led to the outside. So, when the prisoners asked the guard to open the door for them, he thought he was opening a cell door not an exit door.

The escapees then scaled the fence using prison blankets. Eleven out of the prisoners were captured within 12 hours, with the last (Brady Andrew Kilpatrick) captured a few days later in Florida.

If You Don’t Succeed, Try Again – July 1, 2018

French gangster Redoine Faid was serving a 25-year prison sentence for a 2010 failed robbery that killed a policewoman.  On April 12, 2013, he made his first jail break. He used explosives to blast through “five prison doors and break free in the northern town of Sequedin.” Faid held hostages during his escape to ensure his safe getaway. He was arrested a few weeks later in Seine-et-Marne, where he was making plans to escape to Israel.

On July 1, 2018, Faid made his second shocking escape. This time he had three masked men hijack a helicopter and force the pilot to land in the Reau prison courtyard. The criminals were said to land the helicopter and leave the pilot unharmed and take their first getaway car. After a short ride they parked the car in a shopping mall and set fire to it, and reportedly continued their escape in a white van.

Faid was caught 3 months later in France with three others.


Image Source: CNN

Did we get them all? Let us know if there are more bizarre prison escapes out there that you know about!

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