The Top 5 Prison Escape Of All Time

Published on 11/17/2020
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Everybody loves a good prison escape story. While these types of storylines have been exhausted among popular TV shows and Hollywood films in recent years, some of the best prison escapes happened in real life, and have formed a part of the history of the world in a profound way. As the list below suggests, prison escapes in the real world can be considered interesting, puzzling and sometimes even just a little miraculous!

The Top 5 Prison Escape Of All Time

The Top 5 Prison Escape Of All Time

5. The Story of Empress Matilda

Back in 1142, Empress Matilda was surrounded and forced to surrender by soldiers with loyalty to her cousin Stephen. This would eventually become a pivotal moment in the battle for the crown, and as he was the grandson of William the Conqueror, Stephen imagined that he was most entitled to it. Matilda made an escape from Oxford Castle in a freezing, snowy night according to legend, having wrapped herself in a white cape and armed with ice skates. The rest of her life is shrouded in mystery. After a truce was declared, Stephen passed away and King Henry II took to the throne.

4. Busting Out of Alcatraz

Alcatraz has often been the sight of many mysteries, and in June of 1962 three prisoners went missing without a trace. As it turned out, prisoner Allen West had devised a plan for Frank Morris, John Anglin and his brother Clarence to dig an escape route over the span of 24 months. It also involved building a raft to sail to freedom. After dummies were placed in their beds, it was too late once guards discovered what had happened. Investigators found some of their personal items washed ashore, insinuating that they had drowned, but with no bodies being found, this epic escape will forever be shrouded in mystery.

Busting Out Of Alcatraz

Busting Out Of Alcatraz

3. The Ronnie Biggs Escape

Ronald Biggs was well known for his active involvement in the Great Train Robbery of 1963, for which he served 19 months in Wandsworth prison before scaling a wall with a rope ladder and getting away in a waiting van. He lived as a fugitive for 36 years, fleeing to Brussels and eventually ending up in Paris, where he had plastic surgery done to conceal his identity. In 2001, he turned himself into authorities at long last, and he ended up serving 8 years before being released on compassionate grounds. He died at the end of 2013, immortalized forever for his adventurous life.

2. The Biggest Breakout in British History

On 25 September 1983, HM Prison Maze saw a mass breakout of 38 prisoners who smashed their way through the maximum security jail. The jail was widely considered to be impenetrable, so prisoners planned to break out over the course of many months. The prisoners had some help from accomplices, and six handguns were also smuggled into the prison. After seizing control by taking officials and guards hostage and hijacking a truck, the main gate was opened and 38 prisoners escaped on the day.

1. The Incredible Great Escape

In March of 1944, the “Great Escape” took place when Squadron Leader Roger Bushell helped 200 British POW’s to break free from Germany’s Stalag Luft III. The escape involved building three deep, long tunnels underneath the camp fences. A process that involved 600 prisoners, the tunnels were dug 30 feet below and the walls were shored up with wood scavenged from the beds of prisoners. On Friday the 24th, the escape attempt began, but the first man out realized the tunnel had come up short, eerily close to a guard tower. 76 men crawled through before being discovered by guards. 73 were recaptured and half were executed on Hitler’s orders.

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