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Home / Sponsored Stories

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World's weirdest prison breaks

15 Nov, 2018 11:00 AM
Photo / Getty Images.

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Train robber Ronnie Biggs maybe owns the most famous jail break - but which were the strangest?

Prison breaks are the stuff of legend (like legendary movie The Shawshank Redemption). But they are also made up of cold, hard facts – facts often much stranger than fiction.

So what are the five most famous prison breaks? Well, the bust-outs just keep on happening – and because the stories behind them are stranger than anything fictional, we have assembled what we believe to be the world's top five weirdest jail breaks:


1. Escape at Dannemora
This tale is even odder than Shawshank – and is the subject of a new series starting next week on SKY*. In 2015, two inmates, Richard Matt and the aptly-named David Sweat, used power tools to cut through the steel walls of their cell before escaping – aided and abetted by the wife of a prison guard with whom both men had affairs.

Their escape was the first – and only – from the Clinton Correctional Facility in upstate New York. Matt was a double murderer who also dismembered a man and who was, unusually, a gifted artist. Sweat was a cop-killer; their breakout and subsequent journey towards the Canadian border sparked a huge manhunt that cost an estimated US$23 million.


2. The Flying Frenchman
French murderer Pascal Payet has been involved in not one, not two, but three – yes, three – escapes from prison using helicopters.

In all honesty, if anyone told you this in a social situation, you'd struggle to believe them – but it's true. He first "heliscaped" in 2001, when friends collected him from the roof of a village prison in a helicopter. Two years later, he repeated the arrangement to help three more prisoners escape.

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Payet was caught and sentenced to 30 years in prison for murder in 2005. Two years later, in spite of being watched constantly, under the cover of Bastille Day celebrations, he jumped into a hijacked helicopter. He was found months later, near Barcelona, and transferred to a secret location, where he now remains…we think…Wherever he is, those watching over him will be on high alert if they ever hear a helicopter.


3. Cheeky Chapo
In a prison bust that made international headlines and involved a real-life Hollywood movie star who wasn't acting, infamous drugs baron Joaquin "El Chapo" Guzman (El Chapo translates to Shorty) had spent about a year in prison in Mexico (after 13 years on the run) when he broke out again.

El Chapo was the hugely wealthy head of the Sinaloa drugs cartel. Over the years, he made multiple escapes, becoming a weirdly popular kind of folk hero. This one came when Guzman exited his cell through a hole in his shower that engineers estimated to be a mile long and to have cost about US$1m. The body of a sparrow was recovered from the cell – leading to the theory El Chapo used the bird to test whether the air in the tunnel was safe.

The weirdness continued when movie star Senn Penn, writing for Rolling Stone magazine, interviewed Guzman on the run, though he was captured the day after the story was published.


4. Korean contortionist
Choi Gap-Bok knew yoga well – so well, he invented a new method prison escape. Choi had practiced yoga for 23 years when he was arrested on suspicion of robbery in 2012 and was put in a police cell in Daegu, Korea.

Five days later, he applied skin ointment on the upper part of his body and slipped out of the slammer by squeezing through a tiny food slot at the bottom of the cell. The 1.62m Choi somehow inserted his body into a space 15cm tall and 43cm wide. He was caught six days later and returned to a cell. With a smaller food slot.


5. Frank-ly unbelievable
Frank Abagnale, whose con man exploits were captured in the 2002 movie Catch Me If You Can, flew around the world pretending to be a Pan Am co-pilot. He also engineered a jail break which hinged on deception rather than break-outs as in the previous four examples.

Sentenced to 12 years in prison in the US, Abagnale was taken to jail by a marshall who forgot his prisoner's papers. While he was gone, Abagnale persuaded guards he was actually an undercover prison inspector – a ploy often used to test security. They bought it.

With "credentials" established, Abagnale used a female friend to fake two business cards – one for him, as a prison inspector, the other for her as an FBI agent. Abagnale produced her card (with phone number), told the guards he needed to speak to her; she told the guards she needed to meet him outside the prison – and Abagnale walked free. He was caught two weeks later

*Escape at Dannemora, SKYs new eight-week series premiering on SoHo November 19, was directed by Ben Stiller and stars Benicio Del Toro, Paul Dano and Patricia Arquette as the woman involved with both of them.

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