The Five Most Badass Jailbreaks You Haven’t Heard Of

There is an old Chinese proverb that says “abuse a man often enough and he will become freakin’ MacGyver.” While this bit of Confucian knowledge might be somewhat obscure, we assure you that it’s perfectly true. Any prison in the world, no matter how secure, cannot hold a determined man with a lot of time on his hands. In fact, the tougher the prison the more ingenious and incredible the escape method used to get the hell out of there. Here are just some of the world’s most incredible jail breaks:

Colditz Castle Glider

During the Second World War the Germans had one serious problem, we’re talking early in the war so Russian tanks parading through Berlin wasn’t an issue yet. As the Third Reich slowly spread through Europe the Nazis realized they had no idea what to do with all the prisoners of war they captured. Most of these prisoners were war veterans, British pilots or members of the French resistance. In other words these were men with balls of steel and enough intelligence to fashion a weapon out of a paper clip and a cat. This meant that the average prison couldn’t really hold them for more than a few hours, at most a few days.

Pictured: British flight ace held captive in Colditz. Not pictured: his enormous balls.

The history of the Second World War is filled with brave men that managed to escape the German POW camps in innovative ways. Maybe you saw that old movie called The Great Escape, the one where several hundred men escape by digging a tunnel out of a German camp with nothing but a few spoons. It turns out that movie is based on real events that not even Hollywood could exaggerate.

In order to keep these kinds of inventive jail-breakers from escaping, Nazi officers decided to move the most “high risk” prisoners into a medieval fortress located on the side of a cliff. Colditz Castle was an eleventh century stronghold, surrounded by high walls, which were in turn surrounded with barbed wire and patrolling German officers. The castle was thought to be impenetrable and impossible to escape from.

Colditz Castle

Of course this didn’t stop the Dutch and British soldiers who were housed in Colditz Castle from trying and often successfully jail breaking. The prisoners build a wireless radio that allowed them to contact the British counter-intelligence. With this outside help they managed to forge papers, bribe guards and sneak out of Colditz. Despite harsh punishments and constant raids by German wardens the radio equipment was never discovered. The Germans also never managed to discover the glider built by two British pilots towards the end of the war. Yes, you read that right: the British prisoners were planning to use a glider to fly out of the German camp. This is considered, by far, the most innovative method anyone ever tried to use in order to escape from a prison.

More or less like this.

The Colditz Glider was built in complete secrecy despite the fact that its wing-span measured 32 ft and it was about 19 ft from tip to tail. It was composed entirely out of stolen materials and held together with improvised glue. The whole contraption weight less than 200 kg and should have been launched by a serried of pulleys, which could accelerate it to 30 mph. Unfortunately, the war ended before the two pilots could try out their contraption. Nonetheless a later test proved that the machine could have flown without any problems carrying the two pilots to safety. It’s really a shame they never got to fly over the German walls showing the bird to all the confused German guards.

Andre Devigny

While the Colditz Castle Glider might have been the most ingenious approach to jail breaking Andre Devigny is probably the biggest bad-ass to ever escape from a German POW camp. Andre started out as a member of the French Resistance, which already puts him in an elite class of men. However he proved that he was manlier than Chuck Norris when he was captured and sent to Fort Montluc. In case you’re not up to date on which are the most horrible prisons in the world, trust us, Fort Montluc is up there.

Basically the whole place is just huge walls.

Since prison by itself wasn’t bad enough, the Nazi also had a special program for the prisoners housed there, a program composed mostly out of horrible torture. Yet despite two weeks of brutal interrogations Andre never revealed any information, instead focusing on planning his escape. He attempted to jail break so often that the guards, probably tired of trying to stop him, chained Andre to the walls of his cell and convinced their superiors to have him sentenced to death.

At this point, after being tortured for days, having failed to escape numerous times, and hearing that they will soon die, most men would probably give up. Instead, Andre used a safety pin to remove his handcuffs and filed down a spoon turning it into a sharp tool he could use to remove the tiles of his cell. He then created a grappling hook out of an old lantern and using bed sheets as a rope, Andre climbed through a skylight. Once outside the cell block he wrestled a German guard, killing him with his own bayonet. Andre then flung himself over a 15 feet gap, using the grappling hook to land safely on the other side of the prison’s massive walls. Now keep in mind, that he was doing all this Batman routine after being tortured over the course of two weeks so he was nowhere near the peak of his physical condition.

The guy was basically the Dark Knight.

German troops started a manhunt as soon as they had found the empty cell, but Andre hid in ditches and covered his scent with mud, managing to avoid all attempts to catch him. He made his way to Switzerland, where he joined the French liberation Army and returned to occupied France to kill some more Nazis.

Jack Sheppard

Moving away from World War II we decided to look at a man that basically wrote the book on how to escape from prison, a young thief from London, by the name of Jack Sheppard. During the 18th century Jack was probably one of the most well known robbers in the world, mostly because the police simply couldn’t keep him locked up.

The man wrote the book on Jail breaking.

He was first arrested in 1724 for a minor burglary he committed with his mistress and brother. Brought in for questioning he escaped the same night, by breaking through the prison’s wooden roof and lowering himself down on a rope made out of bed sheets. When people gathered around to see what the commotion was, Jack screamed that he saw the escaped prisoner still on the roof. It took the police hours to figure out that there was no one on top of the building.

Unfortunately for him, Jack was quickly captured, when a former friend betrayed him. Arrested again, along with his mistress, Jack removed one of the cell’s bars and used the same rope out of sheets trick to lower himself into the jail’s courtyard. Once there he somehow managed to climb a 22 foot wall and escape along with his lover.

Having become a minor celebrity Jack attracted the attention of London’s biggest crime lord, Johnathan Wild. However, Jack refused to work for him and in an ironic twist the crime lord bribed police officers to arrest Sheppard. Back in jail, Jack used another inventive jail breaking method that has been copied hundreds of times since. He dressed himself in women’s clothing and basically walked out.

Afraid that their reputation will be tarnished and pushed by Wild’s bribes the police started a large manhunt, managing to capture Jack almost a year later. Not taking any changes the police locked Jack in a special cell, his feet and hands bound with iron locks.

Look at the size of that lock!

Of course, being tied up in the eighteen century equivalent of a high security prison didn’t really prevent Jack from escaping. He broke free from the cuffs, climbed through the cell’s chimney, removing several metal bars in his way and broke into the room above his cell. Once there he managed to lock-pick six different doors, making his way onto the roof of a nearby house. He broke into that house and walked out the front door into the night, without anyone hearing him do any of this.

The famous writer, Daniel Defoe, wrote that Jack Sheppard must have been helped by the devil. There is no other way to explain his mysterious escapes.

Winston Churchill’s Escape

Few people know this about Winston Churchill, but he started out as a journalist and, since young journalists are expendable, one of his first assignments was covering the 1899 war in South Africa. This was the second war in the area and it was lengthy and brutal with many casualties on both the British and the Boer side.

People were a lot more intense back then

Only 24 at the time of the conflict Churchill managed to get himself caught and thrown into a Boer POW camp. Always a great observer Churchill quickly noticed that there was a gap in the patrol routine. He planned a perfect moment when no one would be watching the 10 foot wall surrounding the camp, and he made a run for it. Before escaping Churchill, always the gentleman, made sure to leave money for a bill to a local shopkeeper where he had an account along with letters for a few local politicians which he had befriended. We like to think that he also stopped to grab a cup of tea.

However, the really impressive part of Churchill’s escape is the way he took to get back home. Since the whole area was occupied by enemy forces, Churchill made sure to lay low following the train tracks and avoiding the large manhunt tracking him down. He slept in ditches during the day and rummaged through trash looking for newspapers which kept him informed about the course of the war. In total Churchill traveled almost 300 miles, over the period of six days eventually arriving in the Portuguese colony of Delagoa Bay.

Imagine six days of walking through this.

The story of his escape and subsequent travel through South America made Churchill a hero in Great Britain and helped launch his political career. However, before focusing on politics Churchill returned to the front, joining an army expedition into India. Turns out that when you’re Winston Churchill barely escaping alive out of South Africa is only the appetizer for some Indian warfare.

Tunnel Joe

In the 1950’s the Maryland penitentiary was considered one of the hardest prisons to escape from. It was a massive granite building where no amount of rope made out of sheets could help you make a run for it. However, on February 17th Joseph Holmes proved that nothing can stop a man who is determined to work for his freedom.

There are many stories of prisoners that tunneled their way to freedom, yet most of these stories involve at least a dozen people who worked together, around the clock. Holmes was one single man who managed to dig a 70 feet long tunnel, breaking through more than a foot of concrete in order to reach the outside. In doing so he used nothing but scraps of iron and spoons he could sneak from the meal room. The whole operation took nineteen months to complete, most of that time spent in an extremely narrow, poorly lit, underground corridor.

Basically like this.

During the whole time he was digging tunnel Joe also made sure to plan what will happen once he escaped. Unlike most people who jail break, he had a plan to leave the country and gathered money in order to make that plan happen. In total he saved up over $150 though the illegal black market. The man set up a whole network of trade, just to fun his post prison escape plans.

The man’s a financial genius!

During the months of work Joe made sure to always have clean clothes and he often dug his tunnel naked in order to avoid suspicions. In order to deal with the dirt he would flush it down the toilet, literally tons of it, always making sure that no one became suspicious. He even somehow managed to fashion himself a kerosene lamp in order to see where the heck he was going.

Although he was eventually caught again Tunnel Joe remained a Baltimore celebrity due to the impressive perseverance he showed in pursuing the one goal of becoming a free man once more.

Via ForkParty