The 10 Greatest and Most Infamous Prison Breaks of All Time

biggest prison breaks in history

The news, television and movies – it seems like no matter where you turn you can find some sort of show or reference to prison. Those of us who aren’t in prison are fascinated by the life that goes on behind the razor-wire and concrete walls. For us, the closest we’ll come to the prison experience is by watching an episode of Orange is the New Black, OZ or The Shawshank Redemption. Conversely, those behind bars are probably not as keen on prison life. After all, without Morgan Freeman around to narrate the daily events, things can probably get downright boring. In some cases, inmates are so set against staying in their concrete and steel dwelling that they’ll do anything to get out, even if it means getting killed or spending the rest of their lives on the run.

Most recently the escape of two convicts from an upstate New York prison facility caught the attention of the country and every media outlet. In a storyline fit for an HBO special, we learned of corrupt prison guards, smuggled tools, escape plans and rehearsals and then days on the run through the New York countryside. Yes, prison and the life of the prisoner makes for a captivating story at times. It adds yet another element to the world we, as outsiders, love to watch on film and television. Nonetheless, not all escapees are an Andy Dufresne or Luke Jackson. From violent and dangerous criminals to prisoners of war, no matter how long or how well we’ve built prisons, people have been trying and succeeding when it comes to breaking out of them.

The following looks at 10 of the biggest, most infamous or most famous prison escapes in history. From single escapees to groups of hundreds, from the Civil War to the Second World War, these break outs required planning, patience and nerves of steel. Some of these escapes have been documented in film and literature. Others, you may not be so familiar with. From ‘The Rock’ to Nazi Germany, from Northern Ireland to Afghanistan these prison breaks are all pretty spectacular in their own unique ways.

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10 John Dillinger

Via nbcchicago.com

Robber and gangster John Dillinger was one of the more notorious figures to make a mark during the Depression-era in the United States. Dillinger was involved in the robbery of dozens of banks and even police stations and was even charged with the murder of a police officer. In 1934, he was caught and imprisoned in Crown Point Jail, Indiana. The prison was labelled as ‘escape-proof’ but someone forgot to tell Dillinger. On March 3, 1934, the gangster took a guard hostage and escaped using the sheriff’s car. While those involved in the hostage taking and escape swear the gun Dillinger used was real, others, including the FBI, feel that Dillinger made his escape using a pistol carved from either wood or a potato.

9 Libby Prison 1864

Via civil-war.net

It would be an understatement to say that the Civil War was a pretty horrible time for all those involved. It would be an even bigger understatement to say that soldiers captured and imprisoned during that conflict faced a terrible time in the POW facilities. A Civil War military prison was a dirty and dangerous place to be on the best of days. Lack of food, rampant disease and uncertain treatment at the hand of your captors all made the ordeal rather challenging. That’s why, in 1864, the Union soldiers being held in Libby Prison, a Confederate facility in Richmond Virginia, decided it was time to escape. In order to keep their escape tunnel a secret, the escapees dug in a rat infested part of the facility which Confederate guards did not keep watch over as tightly. Over 12 hours, 109 prisoners escaped while the guards had no clue what was going on. In the end, half of those who escaped made it back to Union lines.

8 Imrali Island

Via therumpus.net

The word on the street is that as far as prisons are concerned, Turkish prisons are pretty bad places. In 1970, American student Billy Hayes found this out the hard way. Hayes had been caught with a few pounds of hashish and was charged with drug smuggling. He was sentenced to four years which magically increased to life (later dropped to 30 years) when he was near the end of his initial sentence. Not willing to spend the rest of his life in a Turkish island prison, Hayes escaped in a rowboat in 1975 while working on the docks near the prison. He made his way to Istanbul, disguised himself the best he could and eventually worked his way to Greece. Once in Greece he was detained by officials and deported to the United States.

7 Sarposa Prison

Via theblaze.com

This Afghanistan prison could actually be used twice on this list because it has been the scene of two major breakouts. In 2008, the Taliban launched a not-so-subtle break out which involved the use of suicide bombers and armed men to blast their way into the prison. This raid freed around 1000 prisoners including over 300 Taliban members. In 2011, not resting on their laurels, the Taliban dug a 350 meter tunnel into the prison from the outside, breaking through the floor in one of the cell blocks. For four hours inmates escaped through the tunnel before it was detected by guards. In the end, another 500 prisoners had escaped to add to the nearly 1000 freed three years earlier.

6 The Maze Escape

Via paddys-wagon.blogspot.com

Her Majesty’s Prison Maze was considered one of the most secure facilities in the world. It had 15 foot high fences, thick concrete walls topped with barbed-wire and numerous wires strung across the facility to prevent any helicopter escapes. In 1983, 38 Irish Republican Army (IRA) members who had been imprisoned in The Maze broke out. Using guns smuggled into the facility, the escapees used guards as hostages as they took over the cell block. With captured keys, they were able to open doors and get access to a truck which was delivering food to the prison. All 38 boarded the vehicle and escaped in the largest break out in British history. In the end, only half of the escapees were recaptured.

5 The Great Escape

Via youtube.com

Our second wartime escape on this list, the prison break known universally as The Great Escape is well known thanks to the 1963 film of the same name. In March 1944, several dozen airmen who were being held prisoner in Stalag Luft III, a Nazi German prison camp for captured Allied airmen, made a break out attempt. The plan had been taking shape since the spring of 1943 and for a year the prisoners had dug tunnels under the camp – the whole time under the watchful eye of prison guards. Initially 200 had been slated to escape, but circumstances meant only 76 were successful in getting out of the camp. Of those who escaped, 73 were recaptured and 50 of those were executed on the orders of Adolf Hitler.

4 Frank Abagnale

Via quandly.com

If you’ve ever seen the Leonardo DiCaprio film Catch Me If You Can then this name should sound familiar. Frank Abagnale was a master criminal. He was an expert at impersonation, counterfeit and theft. Even when he got caught and sent to jail he was an expert at escape. In 1971, while being transferred to a detention facility in Atlanta, Georgia, Abagnale pretended he was an undercover prison inspector – a ruse helped out by the fact the guards had lost his paper work. He then had a friend smuggle in two business cards, one for a federal prison inspector and the other for a fake FBI contact. Abagnale showed the cards to the guards and when they called the number on the fake FBI card they got one of Abagnale’s friends. The friend convinced the guards their prisoner must be let out to report on the situation in the prison. Just like that, Frank Abagnale had fooled his way out of another sticky situation.

3 Pascal Payet

Via blog.mapsofworld.com

Unlike Frank Abagnale, Pascal Payet wasn’t as smooth in his escape attempts. The Frenchman opted to use helicopters to make escapes from the prisons he was held in. In 2001, while serving 30 years for murder, Payet and another inmate used a hijacked helicopter to escape a prison in Southern France. Once out, he didn’t stop there. In 2003 he orchestrated a raid on the same prison to free other inmates using a helicopter. Eventually captured, he was given extra time on his sentence and placed under extra guard. In 2007, four armed men hijacked a helicopter and raided the prison holding Payet. The armed men broke into the prison and freed Payet, taking him away in the helicopter. The James Bond style escape didn’t have a happy ending for the Frenchman, however. Months later he was captured in Barcelona and returned to prison with even more added time.

2 The Sobibor Uprising

Via ushmm.org

This break out attempt wasn’t made from a prison, nor was it made by convicted criminals – but it deserves a spot on this list nonetheless. During World War Two, Sobibor extermination camp was used by the Nazis to murder approximately 250,000 Jews and Soviet POWs. In October 1943, prisoners Leon Feldhendler and Alexander Pechersky led an uprising of nearly 600 prisoners. Having smuggled rifles and ammunition to some of the Russian POWs, the inmates began quietly killing the SS guards one at a time using axes and knives. After several guards had been killed the prisoners made their move to escape. Escapees had to get through the barbed-wire fencing and cross a minefield to reach a forest – all the while being shot at by the remaining camp guards. In the end, of the 300 who made it to the woods, 60 eluded capture until the final defeat of Nazi Germany in May, 1945.

1 Alcatraz

Via en.wikipedia.org

Located on an island in San Francisco Bay, Alcatraz is probably the most well-known prison in the world. Although no longer in use, from 1934 to 1963 this prison housed the most notorious convicts in American history, including the likes of Al Capone and James “Whitey” Bulger. Alcatraz’s claim to fame was that it was impossible to break out of. Naturally this didn’t stop people from trying. In June 1962, three inmates undertook their escape having chipped through their cell walls with spoons. While the break out was occurring, the guards were being fooled by papier-mache heads the prisoners tucked into the beds to make it appear as if all was normal. Braving the cold temperatures and strong currents the three swam to freedom – sort of. No bodies were ever found, although experts predicted the three drowned swimming to the mainland.

Sources: time.com, telegraph.co.uk, bbc.com

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