The 7 Biggest Prison Breaks of All Time

Prisoners have plotted their escapes for as long as prisons have existed. And in some cases, their detailed plans of an escape became a reality when they made it out on the other side. Regardless of how secure or escape-proof a prison is said to be, there will always be one prisoner who is smart enough and courageous enough to try to escape and, in some cases, succeed. Here are the seven biggest prison breaks of all time.

  1. Colditz Castle (1945):

    The Colditz Castle was touted as being the Nazi’s most secure prison during World War Il, but the German POW camp also had a surprisingly high number of escapees. Polish, English, French, Dutch, and other inmates managed to find their way out of Colditz Castle, but out of the 130 that escaped, only 30 actually got away. The first prisoner to make a clean getaway from Colditz was French Lieutenant Alain Le Ray, who hid in a cellar of a house in a nearby park before safely fleeing to Switzerland. One of the most famous stories of Colditz Castle was the greatest escape that never happened. In 1945, a group of British prisoners secretly built a glider out of wooden shutters, mattress covers, and mud, which they were going to use to escape. The war came to an end before the men had the chance to fly their glider out of prison, but it is now regarded as one of the most genius prison escape vehicles of all time.

  2. Libby Prison (1864):

    The incredible Union soldier escape from Libby Prison, Richmond, Va., is one of the most celebrated stories in all of Civil War history. On the night of Feb. 9, 1864, 109 Union officers crawled through tunnels they built from the prison basement into a nearby yard where they regained their freedom and some returned back to Union lines. The elaborate tunnel project was orchestrated by some of the most prominent prisoners in Libby. Their escape completely surprised guards and the Confederates, who were unaware of their ingenious plan.

  3. Alcatraz (1962):

    Alcatraz was touted as being America’s most secure prison and virtually impossible for prisoners to escape. Several inmates tried to flee during Alcatraz’s 29 years of operation, but only one group of prisoners are said to have successfully escaped the premises. Prisoners Frank Morris and John and Clarence Anglin allegedly dug their way out of prison using a metal spoon and a homemade drill. The cleverly muffled the sound of their drilling with accordions that played for one straight hour a day. They even placed papier-mache dummies in their cells while they worked on their escape. Although the prison rejects this story and claims the men drowned at sea, their remains have never been found.

  4. The Maze (1983):

    Northern Ireland’s Maze prison was home to some of the most notorious criminals during the Troubles conflict. Many paramilitary prisoners tried to escape the highly secure prison, but in 1983, a group of 38 IRA prisoners succeeded. The prisoners used smuggled guns to escape H-Block 7. They killed one guard and wounded several others before taking the passengers of a food delivery van hostage and using their vehicle to escape prison grounds. Some 19 prisoners, including escape leader Bobby Storey, were caught days after the high-profile escape and were taken to different safe houses around the world and others were returned to the Maze.

  5. Stalag Luft III (1944):

    One of the biggest and most well-known prison breaks took place at Stalag Luft III, a Nazi maximum-security work camp. The Great Escape, as it’s called, was an attempted escape by Allied prisoners during World War II. More than 600 prisoners worked on the Great Escape project by digging three tunnels that were hidden in various parts of the prison. They worked on the underground tunnels from April 1943 to March 1944, and the escape leader, Roger Bushell, prepared forged papers for the 200 expected escapees. On the night of the escape, the inmates discovered that the tunnel was too short and ended near a guard tower. Only 76 men successfully escaped, and all but three were captured and returned to prison.

  6. Lake County Jail (1934):

    John Dillinger was one of America’s most notorious gangsters and smartest escapees. While serving time in Lake County Jail, Crown Point, Ind., for killing a police officer, Dillinger and his band of cohorts broke out of the supposedly “escape-proof” jail using a wooden gun he whittled himself. He imprisoned guards before hopping into an unexpected getaway vehicle – the sheriff’s car. This incredible escape happened just months after Dillinger and his outlaws escaped from an Ohio jail.

  7. Imrali (1974):

    Billy Hayes’ escape from Imrali Island in the Bosphorus Strait was one of the biggest prison breaks of all time. The 23-year-old American student was sentenced to four years in prison for attempting to smuggle hashish out of Turkey. He was transferred to Imrali and given an extended sentence of 30 years. Fed up with his sentencing, the young prisoner escaped in rowboat while working on the docks. Hayes fled to Istanbul, dyed his hair, and moved to Greece. He remained there until he was deported to the United States several years later. His book Midnight Express inspired the movie of the same name, but Hayes dismisses many of the events and violent acts that were in the film.