20 of the Most Daring Prison Escapes of All Time
Three Inmates Break Out of Orange County Jail
In January 2016, three inmates of Southern California's Orange County Men's Central Jail used a combination of cutting through walls, crawling through tunnels, climbing, and rappelling to break out of the maximum security prison. The plan was aided by a fight between other inmates, which may or may not have been part of the plot, that delayed the normal head count - meaning the escapees had a 16 hour head start.
The three men, Jonathan Tieu, 20; Bac Duong, 43, and Hossein Nayeri, 37, were awaiting trial for violent crimes, including murder in the case of Tieu. They also likely had help acquiring tools and possibly being picked up after they escaped. Duong turned himself in a few days after the escape, while Tieu and Nayeri were nabbed after San Francisco police received a tip that their stolen white van was in a Whole Foods parking lot. A prison teacher was also taken into custody on suspicion of providing Nayeri maps and tools to aid in the escape.Mexican Drug Lord Sneaks Out Through the Shower
In July 2015, the Mexican drug lord Joaquin "El Chapo" Guzman escaped through a 20 inch hole in the shower area of his cell block at the maximum security Altiplano Federal Prison. Guzman, the leader of the vicious Sinaloa drug cartel, escaped through a lighted and ventilated tunnel system that stretched almost a mile, ending up at a half-built house outside the prison.
This wasn't Guzman's first escape - he escaped from another prison in 2001 by hiding in a laundry cart, and eluded authorities until 2014.
Authorities immediately began a manhunt and questioned prison employees to determine whether Guzman had any help from the inside with his escape. He was able to elude the dragnet for six months later, until he was finally re-captured in January 2016.
While Mexican officials were light on details, it was revealed that Mexican marines acted on an anonymous tip that the drug lord was hiding out in a small house in the seaside town of Los Mochis, and moved in. Chapo apparently didn't go down without a fight - at least five people were killed in the gun battle that preceded the cuffs going back on him. Marines also found a small arsenal in the house, including a rocket launcher and multiple 50 caliber sniper rifles.David Sweat and Richard Matt Escape from New York
Clinton Correctional Facility inmates David Sweat and Richard Matt were the subject of both international headlines and a gigantic manhunt after breaking out in June, 2015. The duo meticulously planned their escape, creating realistic dummies of themselves with fake heads adorned with their own hair. Then they cut holes in the walls behind their beds, using tools provided by sympathetic prison employee Joyce Mitchell . Once in the walls, they cut into a two foot diameter steam pipe and crawled their way to freedom. Mitchell was supposed to pick the pair up at the manhole they climbed out of, but got cold feet and checked herself into a hospital - after which she was arrested.
The two trekked north, staying in hunting cabins and nearly being caught several times before splitting up and taking different routes. Hundreds of police and federal agents took to the woods of New York state to find the pair, and were eventually successful. Matt was found and shot dead on June 26, and Sweat was captured alive two days later.Ted Bundy Escapes from the Library
After he was captured in Colorado, vicious serial killer Ted Bundy had one last trick up his sleeve. It involved the maneuver that’s traditionally saved for particularly crazy perps on Law & Order: he represented himself in court. As part of his “education,” Bundy was allowed to visit the prison library by himself. He had already been excused from wearing handcuffs in court, presumably so he could make grand gestures and pound on a table.
Once he was alone and unfettered, Bundy simply jumped out of the second-story library window and made a run for it. He was captured a week later, and soon escaped again (through a hole he’d sawed in the ceiling of his cell) and made his way to Florida – where he committed three more murders before being captured once again.Richard McNair Mails Himself to Freedom
Convicted murderer Richard McNair had already escaped from a prison in Louisiana by running out of an interrogation room and crawling through an escape tunnel. But his 2006 breakout was legendary in its simplicity. He had gotten a job in the prison mail room, and took the opportunity to hide in a pile of shrink-wrapped packages.
Once he was mailed out of the prison, he moved north, quickly being stopped by a police officer. But in an early viral moment, he was filmed by a police dashcam blathering his way out of being arrested – despite giving multiple names during the conversation and matching the description of an escaped fugitive. He was eventually tracked down in Canada, thousands of miles from the prison, and recaptured.The 22 Escapes of Brian Bo Larsen
Danish career criminal Brian Bo Larsen has escaped from various Denmark prisons an astonishing 22 times, sometimes by digging through or under walls, other times by smuggling himself out with garbage. He most recently busted out in 2014, escaping Vridsloseselille prison outside Copenhagen by sawing the bars off his cell window with a hacksaw. He then used a rope ladder to climb to the top of the roof, then another to climb back down to freedom.
In this case, freedom didn’t last long, as Larsen was arrested after plowing a stolen car into a ditch while high on drugs.The Greek Robin Hood Catches a Helicopter
Famed Greek bank robber Vassilis Paleokostas (known as the “Greek Robin Hood” for giving away his hauls) was thought to be uncatchable, but finally went to prison in 2000 for a kidnapping. In 2006, he planned a daring escape from jail, with the help of two accomplices who hijacked a helicopter and landed it in the prison yard. The prison staff were caught off-guard, thinking the chopper actually was part of an impromptu inspection. Paleokostas was able to get out and spend two years on the run, before being arrested again.
And once again, Paleokostas broke out of prison thanks to an accomplice landing a helicopter in the prison yard. Since then, the robber has continued hitting banks and giving much of the stolen loot to the poor of Greece. He’s still at large.Jose Espinosa and Otis Blunt Copy Hollywood
Convicted killer Jose Espinosa had only a thick gauge wire at his disposal when he scraped the mortar away from the cinder blocks on the outside wall of his cell. He then broke up the bricks using a wheel from a water pipe and hid the chunks in his footlocker. By the time he was done, he’d dug a 16" x 18" hole that was just wide enough to get a person through. His cell-block neighbor Otis Blunt used the same tools to burrow into Espinosa's cell, and the two broke out together. Just to be safe, they left dummies in their beds – and also left a taunting note thanking their cell block guard for giving them the tools they used.
To add a Hollywood twist to the plan, the two men used posters of girls in bikinis to cover the tunnel – the exact same plan used in the film The Shawshank Redemption. Unlike Tim Robbins, Blunt and Espinosa were recaptured and sent back to prison – where they pleaded not guilty to charges that they’d tried to escape.The Alcatraz Escape
While many inmates had tried to break out of the famous island prison of Alcatraz, few had gotten far. Finally, in 1962, three men got out. They dug out of their cells, climbed to the top of the cell block and cut through bars on the ceiling to make it to the roof via an air vent. Now outside, they climbed down a drain pipe, hopped over a chain link fence, and then ran to the shore where they assembled a pontoon-type raft, and sailed into San Francisco Bay.
They were never seen again, and while it’s quite likely they drowned, it’s also not out of the question that they made it to the mainland and disappeared into the city.John Dillinger's Wooden Pistol
In January 1934, bank robbing celebrity John Dillinger was arrested in Tucson, AZ, after locals recognized his accomplices. He was extradited to an “escape proof” jail in Indiana, but just a month later, he forced his way out of the main cellblock - brandishing a phony gun. Dillinger claimed he had fashioned it himself from wood, a razor handle, and black shoe polish, information later suggested that one of his lawyers smuggled in.
Showing amazing gumption, Dillinger used the wooden pistol to round up several guards, steal a Thompson sub-machine gun, grab the sheriff’s personal police car and head to Chicago. Three days later, he and Baby Face Nelson robbed a bank in Sioux Falls.Escape from Turkey
In 1970, 23- year-old New York student and small-time drug mule Billy Hayes was arrested attempting to smuggle hashish out of Turkey. He was sentenced to four years in prison and sent to the notorious Sağmalcılar Prison in the Bosphorus Strait.
Just weeks from being released, Hayes received an extended sentence of 30 years (for no apparent reason), and decided enough was enough. Hayes took advantage of his job working on the prison dock to steal a rowboat and sail to Istanbul. He then dyed his hair and made it to Greece, finally being deported to the US. In 1977, Hayes wrote the book Midnight Express about his ordeal, which was then adapted into a film by Oliver Stone.Maze Prison Breakout
It was the biggest prison break in British history, which, given the history of Britain and prisons, is saying something. On September 5, 1983, 38 Irish Republican Army (IRA) prisoners escaped from H-Block 7 of the notorious Maze prison in County Antrim, Northern Ireland. And since H-Block was encased in a field of walls and razor-wire fences, they did it the old-fashioned way: they overpowered the guards and took their guns. Then they hijacked a supply truck, tied the driver’s foot to the clutch, and drove out.
Half of the group were recaptured, but the other half managed to avoid the authorities and make it to the US. A few are still at large, having been given amnesty by the British government. The Maze itself was closed in 2000.The Libby Prison Break
In 1864, more than 100 Union soldiers broke out of the Confederate Libby Prison in Richmond, VA. Some of the men had figured out a way to dig a tunnel from the prison basement, a dank and dark pit they nicknamed “rat hell.” After a couple of weeks of burrowing, they dug upwards and emerged inside a tobacco shed in a farm field, well away from the prison. One hundred and nine Union soldiers eventually escaped through the tunnel before it was closed down. Many were recaptured and a few died later, but it turned out to be the largest prison escape of the Civil War.The Taliban Prison Breakout
On April 25, 2011, more than 480 imprisoned Taliban insurgents escaped Kandahar’s Sarpoza Prison through an underground tunnel that had been dug from the outside in. The tunnel stretched over 1,000 feet, and because it was dug by insurgents outside the prison going inside it, rather than the other way, there was no need for secrecy, nor a way for the guards to discover it.
Four hours proved to be enough time to get hundreds of men out, and the tunnel was only found after the inmates had been squirreled away to various safe houses. Few of the prisoners have been recaptured, and many are thought to have again taken up arms against the US.The Cowra Breakout
The biggest organized prison breakout in any Allied country in World War II was the Cowra Breakout, taking place in the small Australian town of Cowra. The town’s prison camp held a large number of Italian and Japanese prisoners, along with small numbers of other nationalities – all held in a massive swath of land hundreds of miles from any major city.
On August 5, 1944, over 1,100 Japanese soldiers attempted a mass breakout, using knives, studded clubs and thick wires. They set their huts on fire and stormed the wire keeping them in. Despite facing down guards armed with machine guns and rifles, the horde of prisoners broke through the wire and fanned out into the desert. Over 200 were killed in the breakout, with others being killed or committing suicide later. Within 10 days, the entire group had been recaptured or killed.James Robert Jones: On the Lam for 37 Years
In the midst of serving a 23 year stint in military prison for murder, Private James Robert Jones escaped from Leavenworth and disappeared. He made his way east using a fake name and false papers, and settled in Florida. He managed to stay on the outside for an astonishing 37 years, until US Marshals finally caught him by matching up his face in a database of fugitives.
Jones was arrested without in incident in 2014.Choi Gap Bok Squeezes Through a Foot Slot
Korean petty thief Choi Gap Bok was also a yoga master, having practiced the art for over 20 years. His skill and flexibility came in handy when he landed in prison in 2006 – and squeezed himself through his prison door’s tiny food slot. And tiny means tiny – 6 inches by 18 inches. Choi used skin ointment to make himself slippery, then pushed himself through the slot in 34 seconds.
While he was caught less than a week later, Choi quickly became famous as a Korean Houdini – and is now in a prison with a food slot half as big as the first.Jean-Pierre Treiber's Cardboard Escape
French double murderer Jean-Pierre Treiber constructed a cardboard box (normally part of his job working in the prison’s stationary department), placed it on the loading dock and crawled inside. It was then loaded onto a truck and driven away, by someone who didn’t seem to question why one box was so much heavier than the others.
Once on the road, Treiber cut through the tarp covering the truck bed and hopped out, disappearing into a nearby forest. The guards didn't notice Treiber was missing for nearly seven hours, but he was captured anyway, being found in Paris three months later. He hanged himself in prison the following year.The Parkhurst Prison Escape
1995 saw three inmates of the UK’s Parkhurst Prison, Andrew Rodger, Keith Rose, and Matthew Williams, craft an intricate arsenal of tools and weapons to bust out of the jail on the tiny Isle of Wight. Among these were a 25-foot-long ladder to scale the prison fence, a gun, and a master key that unlocked every door and gate in the prison. They used the key to open a door in the gymnasium, then cut through the inner fence and scaled the outer fence.
After that, they hid for four days in a shed waiting to steal an airplane. Even with all their preparation, they were caught and sent back to prison.The Sobibor Revolt
Unlike other Nazi concentration camps, Sobibor had no other purpose but killing enemies of the regime. When rumors started going around the camp that it was to be closed, with all the inmates murdered, a plan was hatched to kill the guards and walk out. Using homemade knives, a captured Soviet officer and Poles with military experience killed 11 SS guards one by one and cut the outside phone lines into the camp.
When the plan was finally discovered, the inmates made a run for it, with hundreds either being shot or killed in the minefield surrounding the grounds. About 60 made it out safely, and the SS ordered the camp destroyed.
