Craziest Prison Breaks That Will Blow Your Mind

Correctional officers keep society safe by guarding those who need to be locked up. While most escape attempts involve typical methods like smuggling contraband, blackmail, or bribery, some inmates get much more creative. In rare cases, prisoners have used unexpected tools like fruit, yoga, and even helicopters to escape. We’ve put together a list of the 12 craziest international prison escapes of all time. These inmates truly thought outside the box.

Public Enemy #1 – March 3, 1934

We begin with the man whose crimes earned him the infamous title “Public Enemy #1” from the FBI: gangster John Dillinger. A notorious bank robber and murderer, Dillinger escaped from jail twice. His first 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, which was thought to be “escape proof.” However, Dillinger managed to escape with a fake gun, a story that has become famous. Though there’s still some debate about what the gun was made of and how the escape unfolded, many believe it was a wooden gun painted black with shoe polish. Guards were tricked by the fake gun and allowed Dillinger to leave the prison.

While on the run, Dillinger committed a few more robberies before being killed in a shootout with the FBI in July.

The Alcatraz Escape – June 11, 1962

One of the most famous prison escapes, popularized by a movie starring Clint Eastwood, involves three prisoners escaping from Alcatraz, a maximum-security federal prison located on an island off the coast of San Francisco. Known for being “escape-proof” because it was surrounded by water, Alcatraz seemed impossible to break out of. However, on June 11, 1962, Frank Lee Morris and brothers John and Clarence Anglin managed to escape by digging a tunnel through a concrete wall using a spoon.

To buy time, they created paper mâché dummies, using hair from the prison’s barber shop to make them look lifelike, and placed them in their beds. The prisoners then made a raft out of over 50 stolen raincoats and escaped into the water.

The guards didn’t realize they had escaped until the next morning. A search was launched, but the men were never found. The FBI and Alcatraz officials believe the men likely drowned in the water, although their bodies were never recovered.

There’s been speculation that the men survived and moved to Brazil. In 2013, a letter claiming to be from John Anglin suggested he was still alive at 83, and that the other two had escaped with him. The FBI couldn’t confirm the letter’s authenticity, and fingerprint and DNA evidence didn’t provide any clear answers. In 2016, a photo emerged that allegedly showed the Anglin brothers in Brazil 13 years after they escaped, but authorities have not confirmed if it was really them.

Catch Me If You Can – April 1971

Frank Abagnale’s escape story became widely known through the movie Catch Me If You Can, based on his life as a notorious fraudster and imposter. Frank began committing crimes at the age of 15 and managed to escape prison twice. His first escape occurred while he was being deported to the U.S. He managed to slip away from a British airplane at JFK Airport. After being recaptured, he made an even more daring escape in 1971.

In April 1971, Frank used his cleverness to trick the guards into helping him escape. When he checked into prison, a U.S. Marshal forgot to bring Frank’s detention papers. At the time, many prisons in the U.S. were being inspected for civil rights issues, and Frank took advantage of the situation. He convinced the guards that he was an undercover inspector posing as a prisoner for a review. Over weeks, he carefully built his story and even had an accomplice on the outside forge a fake FBI business card to make the lie more convincing.

Believing they were helping the prison pass its inspection, the guards treated Frank like a VIP. Eventually, Frank walked right out of the prison, and the guards didn’t stop him, thinking they had outsmarted him.

He remained on the run for two months before being re-arrested. However, by then, his story had spread, making Frank an instant sensation for his brilliant escape.

Ted Bundy escaped, twice 1977

Ted Bundy, who killed at least 30 young women across the United States during the 1970s, escaped from custody twice. His first escape happened in Aspen, Colorado, in June 1977 while he was representing himself in a murder trial. During a break in the hearing, Bundy was taken to a law library, where he jumped out of a window, falling 30 feet to the ground.

In Aspen, some locals treated Bundy like a hero, with young people wearing T-shirts saying things like “Ted Bundy is a One-Night Stand,” and a restaurant even offering a “Bundyburger.” He was on the run for eight days before being recaptured.

Bundy’s second escape took place later in 1977. He managed to carve a hole in his cell ceiling and crawled through the ductwork. He made his way into a jailer’s apartment, changed into civilian clothes, and then traveled by plane, train, and car to Florida. He was arrested there two months later. Bundy was executed for his crimes in 1989.

An escape in Dannemora, N.Y. 2015

David Sweat and Richard W. Matt escaped from the Clinton Correctional Facility in Dannemora, New York, in June 2015, a prison known for its high security. There wasn’t one simple mistake that led to their escape; they carefully planned and executed their break.

Both men, serving long sentences for murder, cut neat rectangular holes in the steel at the back of their cells. They then climbed down several stories, cut through a steam pipe, and crawled to a manhole about 400 feet beyond the prison walls. The tools they used were smuggled in by a female prison employee.

After an intense manhunt, Matt was shot and killed by a law enforcement officer. Sweat was captured two days later, about 30 miles from the prison.

The Magic Key – January 10, 1995

In a truly unbelievable escape, three inmates in the UK managed to break out of prison by memorizing the outline of a key. Andrew Rodger, Keith Rose, and Matthew Williams worked in the prison’s sheet metal shop, where they created all the tools needed for their escape. They memorized the shape of a guard’s master key and made a replica that allowed them to unlock any door during their escape. In addition, they built a 25-foot steel ladder and even made a homemade gun.

However, their freedom didn’t last long. Just four days later, they were caught while trying to plan a robbery to steal a plane.

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

Pascal Payet, a French robber and convicted murderer, is known for making three successful prison escapes. His most famous escape took place on October 12, 2001, when he managed to break out of a prison in a small French village. He had his friends pick him up from the roof using a hijacked helicopter.

In 2003, Pascal returned to the prison by helicopter and helped three other prisoners escape.

In 2005, he was sentenced to 30 years in prison for the murder of a guard during a car hijacking in 1997. Despite being in jail, Pascal wasn’t done with escaping. In July 2007, he arranged for his friends to hijack another helicopter, take the pilot hostage, and fly it to the prison where Pascal was waiting on the roof. Although 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, better known as ‘El Chapo,’ is a Mexican drug lord and former leader of the Sinaloa Cartel. He has escaped from prison twice. His first escape happened in January 2001, after being arrested on drug charges. El Chapo bribed prison guards to help him escape by hiding in a laundry cart. He managed to stay on the run for 13 years.

In 2014, he was caught again, but just 17 months later, El Chapo escaped once more. This time, he escaped through a mile-long tunnel that ran under the showers of the high-security prison. The tunnel was equipped with lighting, ventilation, and even a modified motorcycle on tracks, likely used for its construction. El Chapo was eventually recaptured in January 2016 and remains in prison.

That’s A Bit of a Stretch – September 2012

South Korean Choi Gap Bok was arrested on September 12, 2012, for robbery. Choi, a yoga practitioner for 23 years, managed to escape from prison just five days later, on September 17. He squeezed through a small food slot that was only 5.9 inches tall and 17.7 inches wide. The entire escape took just 34 seconds. Journalists dubbed him the “Korean Houdini” for his impressive feat, but he was caught again just six days later.

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

David Sweat and Richard Matt, two prisoners at Clinton Correctional Facility, spent months planning their escape. They worked in areas of the prison where they had access to tools, including the kitchen. While walking around the prison grounds, they discovered a pipe under a speed bump that they could crawl through to escape.

Matt also formed a relationship with Joyce Mitchell, the prison tailor, and convinced her to sneak in hacksaw blades hidden in frozen hamburger meat. With these tools, they cut through steel walls and left dummies dressed in prison uniforms in their beds to fool the guards during their nightly checks. They even left a note saying, “Have a nice day.”

Joyce was supposed to meet them outside the prison to help with their escape by providing a getaway vehicle, but she didn’t show up. After several days on the run, Sweat and Matt were eventually found. There was a standoff, during which Sweat was wounded and captured, while Matt was shot and killed.

Joyce Mitchell admitted to helping with the escape and was sentenced to up to 7 years in prison. She is currently serving her time at Bedford Hills Correctional Facility for women and has been denied parole twice.

A Woman’s Touch – 2012

In 2012, Ronald Silva, a drug trafficker, managed to escape from a Brazilian prison. During her weekly visit, his wife gave him the clothes she was wearing and changed into a spare outfit she had brought with her.

Silva then went to great lengths to disguise himself. He shaved his arms and legs, applied fake nails, put on a wig and lipstick, wore heels, and dressed in the outfit his wife had given him. He walked past the guards and out onto the street without anyone noticing. However, as he approached a group of his friends at a bus stop, a sharp-eyed police officer noticed him struggling to walk in the heels and realized something was off.

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

 

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