Breaking out of prison isn't easy. You have to have the right tools, a way to get out of your cell, a way to get to the outside world, and a way to stay on the lam. It helps to have friends on the outside, some kind of special skill like woodworking or yoga, a lot of luck - or just have a helicopter. What are the most well-known successful prison escapes?
Ever since the first prisoner was kept in a blocked off cave, criminals have been figuring out ways to get back to the outside world. Whether they've smuggled themselves out, tunneled under walls, taken hostages, or gotten some accomplices to fly them out, all of these escapees took great risks to reclaim their freedom. And while all of these prisoner escapes were successful in the short term, most ultimately failed. Even the most creative escapee, with the best prison escapes, finds themselves the subject of a manhunt, with limited resources and few allies to turn to. So most get caught and sent right back - where they usually try to escape again.
Here are some of the most well-known and famous prison escapes or breakouts in history. From recent prison escapes, to historical prison breakouts, these people had had enough of life behind bars and took matters into their own hands.
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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.
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 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.
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.
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.
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.
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.
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 Many Escapes of Alfie Hinds
Alfred “Alfie” Hinds was a career criminal, bank robber and deserter, before he was finally pinched in 1953. Hinds broke out after making himself a key for the prison’s front door. He was captured again less than a year later, and when being taken to court for an appeal hearing (he’d done a great deal of legal research while in prison), he locked two guards in a bathroom and made a run for it. He was grabbed again less than a year later. This time, he used a legal loophole to get his sentence reduced – and successfully sued the Scotland Yard detective who had arrested him.
After his release, Hinds published his memoirs and became a huge celebrity in England. He died in 1991, a free man.