3 of the most audacious prison breaks in history

As Mexican drug kingpin Joaquin Guzman escapes prison for the second time, EDGAR looks back on the most stunning breakouts of all time.

Peter Iantorno July 13, 2015

It is fair to say that Mexican drug lord Joaquin Guzman is a difficult man to pin down.

His recent escape from Altiplano Jail (the second time he’s broken out of a maximum-security prison) used an elaborate tunnel more than 1.5km long, complete with lighting, ventilation and stairs.

Of course, to build such a structure on his own without detection would be nigh-on impossible, so the likelihood is that the man they call El Chapo, or “Shorty”, used some of his estimated $1 billion wealth to bribe his way to freedom.

elchapo.jpg Joaquin Guzman, El Chapo.

Just weeks before El Chapo’s escape, David Sweat and Richard Matt busted out of Clinton Correctional Facility in upstate New York by sawing through pipes to get into an underground tunnel system of their own.

Although Sweat was eventually recaptured and Matt was subsequently killed by police, they evaded the authorities for more than three weeks before eventually being tracked down. 

While El Chapo and the New York pair’s escapes have certainly captured the imagination, they are far from the only ones to try their luck. Here are three of the most stunning prison breaks of all time:

Vassilis Paleokostas

Thanks to his numerous large donations to the poor, convicted kidnapper Vassilis Palaiokostas is thought of in his hometown as Greece’s answer to Robin Hood.

But as well as being likened to the heroic outlaw, he’s also known as simply “the uncatchable”, owing to the fact that he has managed to break out of the Greek high-security Korydallos prison not once, but twice!

Even more extraordinary is that he used the same method both times – in both his 2006 and 2009 escapes, accomplices hijacked a helicopter and simply flew it into the grounds of the prison, picking up Paleokostas and allowing him to make his escape.

Although he was recaptured two years after his 2006 escape, Paleokostas remains at large following his breakout in 2009.

Richard Lee McNair

American Richard Lee McNair is criminal who clearly struggles to accept the concept of prison.

While most inmates will get their head down and serve their time, after receiving two life sentences for killing one man and wounding another during a botched robbery in 1987, McNair proceeded to escape from a county jail and two prisons over the following 20 years.

richard-lee-mcnair.jpg The pod McNair constructed to mail himself out of prison in 2006.

His techniques ranged from greasing up his wrists with lip balm so he could slip out of handcuffs and escape from a police station cell in 1988; to crawling out of a ventilation duct to break free from Dakota State Penitentiary four years later; to, in his boldest attempt, mailing himself out of a Louisiana prison in 2006.

While his methods showed some serious ingenuity, unfortunately for McNair, he didn’t have the same flair for evading capture, and he is currently back in the slammer serving an extended sentence.

Choi Gap-bok

Most prison breaks take bribery, accomplices and long-term planning to pull off, however in the case of South Korean burglar Choi Gap-bok’s escape, none of this was necessary.

The 50-year-old had become a master of yoga after practicing it for some 23 years, and he took advantage of his tiny size (standing at just 5-foot-4-inches) and extreme flexibility by squeezing through the food slot in his cell.

Measuring just 5.9 inches tall and 17.7 inches wide, the slot was just big enough for Gap-bok to squeeze his slender frame though, with the aid of some skin ointment, which he applied to the top half of his body.

The incredible escape took just over 30 seconds, and unfortunately for the South Korean, his freedom didn’t last much longer, as he was captured by police six days later and put in a cell with an even smaller food slot.