20 Daring Prison Escapes That Forced History’s Jails To Change

Winston Churchill, then 25 and later to become Britain’s prime minister, was one of the war correspondents captured during the Second Boer War. He was detained at the State Model School, a camp for prisoners of war in Pretoria, South Africa. He scaled a 10-foot corrugated iron wall behind the latrines on the night of December 12, 1899. Other officers were unable to follow, so he did it alone, hitched a ride on a freight train, and escaped to neutral territory. The Boer camps responded by installing barbed wire, electric searchlights, and a nightly roll call.

The Germans built Stalag Luft III with stilted barracks and underground microphones to detect any would-be tunnelers. The escape committee, led by British Royal Air Force officer Roger Bushell, dug a 30-foot-deep tunnel named Harry that passed under them. One night in 1944, 76 Allied airmen emerged from the tunnel. Only three would make it back to their homes. 50 of the recaptured men were executed on the personal order of Adolf Hitler. Germany began conducting two roll calls per day and sealed all possible ways out.

When John Dillinger, America’s top bank robber, escaped in 1934 from the Lake County Jail in Crown Point, Indiana, local authorities were confident that the new prison was escape-proof. Armed with a gun he said he’d whittled from a washboard, Dillinger liberated himself and two machine guns, confined the guards, and sped away in the sheriff’s car. He was gunned down by FBI agents several months later. His breakout forced jails to install sally ports and bolstered the powers of the federal police.

Scottish nobles held Mary, Queen of Scots, captive in Lochleven Castle and forced her to abdicate. At one feast, a teenage page boy named Willie Douglas retrieved the gate keys and rowed Mary across the loch to safety. After that, he shut the gates and tossed the keys into the loch. Her escape reignited a civil war in Scotland. She ultimately fled to England and was later beheaded. Locks with single keys became uncommon after this event. Jailers required two guards for one lock.

Italian writer and adventurer Giacomo Casanova was imprisoned without trial for blasphemy in the Leads, a cell below the Doge’s Palace’s lead roof. Casanova and another inmate once bored through the ceiling with an iron spike, pried up the lead plates, went over the top of the palace, and exited, disguising themselves as ordinary tourists. A Venetian repair log even documents the damage along the route they described, backing up Casanova’s own account. Venice ordered daily tap tests on every ceiling, wall, and floor.

After his abdication, Napoleon Bonaparte, the ex-emperor of France, was not a prisoner on the island of Elba. He was instead appointed ruler of the tiny Mediterranean island, with a British commissioner watching over him. While the commissioner was away, Napoleon escaped past British Royal Navy vessels and headed for Paris. He was later defeated at Waterloo. The second exile took him to the far-flung island of St. Helena, where warships, guns, and guards surrounded his house until his death.

In 1881, William Bonney, better known as Billy the Kid, was being held in the New Mexico Territory’s Lincoln County Courthouse for shooting a sheriff and awaiting execution. After visiting the outhouse, he managed to slip out of his handcuffs and overpower a deputy, shooting him with the man’s own gun. He then killed another deputy with a shotgun, cut his leg irons with an axe, and made his getaway. Sheriff Pat Garrett eventually shot and killed Bonney about two and a half months later. From that point forward, lawmen made sure they had two men with guns for any dangerous prisoner moving between locations.

Willie Sutton, a professional bank robber, had previously escaped through a tunnel from Eastern State Penitentiary in Philadelphia, but his most famous breakout came at Holmesburg Prison. In 1947, Sutton managed to escape along with four other men while a snowstorm raged outside. They were wearing fake guards’ uniforms, and they used a wooden ladder constructed inside Holmesburg’s workshop to scale the outer walls. As one of the guards saw them scaling the wall, Sutton yelled, “It’s okay,” and continued to climb. He avoided capture for several more years. Afterward, prisons began checking guard identification at every gate.

Newgate Prison’s most secure cell was called “the Castle.” Here was locked the young London carpenter Jack Sheppard, condemned to die as a thief. Picking the lock of his handcuffs with an iron nail he found on the floor, he slipped his leg irons and broke through the stone chimney. He then pried away the iron grates and let himself down using bedsheets. Newgate’s wardens responded by chaining high-risk inmates with as much as 300 pounds of iron bolted into the stone floor. Sheppard was caught again and was hanged at Tyburn before the end of the year.

Lieutenant Airey Neave was the first British officer to make it to Switzerland from Colditz Castle, a German camp reserved for prisoners who kept trying to escape. Wearing a fake German officer’s uniform crafted out of painted blankets and cardboard, he crept out of the camp by slipping through a trapdoor hidden beneath the guardhouse’s theater, then strolled past the outer sentries. Afterward, guards bricked up tunnels that were no longer being used and began to scrutinize everyone’s uniforms at the entrance to the camp.

On November 28, 1955, Alfred “Alfie” Hinds, a British jewel thief known by the press as “Houdini Hinds,” used a forged key to break out of high-security Nottingham Prison. He and a fellow inmate then went into the prison’s carpenter’s shop, where they assembled a ladder out of stacked window frames and timber. Hinds then scaled the prison’s 20-foot outer wall and disappeared. The breakout laid bare the way that the keys to British prisons were so loosely kept, and the Home Office immediately began auditing them. It also changed the locks in many prisons.

William Maxwell, the Earl of Nithsdale, was a Scottish Jacobite who was condemned to death and locked up in the Tower. On the night before his scheduled execution, his wife, Lady Winifred Maxwell, came to see him with her friends, all wearing bulky riding cloaks. Lady Maxwell used hers to smuggle in a spare cloak and petticoat. After she changed her husband’s clothes and painted his face, the Earl strolled past the guards, covering his face with a handkerchief, and made it to the continent where he lived out his days. From then on, the Tower searched every visitor who came in, sending female staff to search the women.

Jean-Henri Latude was thrown in the Bastille for life after a scheme targeting Madame de Pompadour, the mistress of France’s King Louis XV. He and another prisoner took 18 months to rip apart linen sheets to make a 140-foot rope ladder and a 208-foot wooden ladder. On February 25, 1756, they made their way up the chimney of his cell, across the roof, and down the outside wall of the moat. The French government subsequently had all the chimney flues in the Bastille fitted with iron bars. Latude was caught and re-imprisoned.

One day, six Irish political prisoners who were imprisoned at Fremantle Prison in Western Australia for “nationalist activities” against British rule simply walked away from their unsupervised work gang. Two buggies drove them to a beach, where they boarded rowboats that took them to the American whaling ship Catalpa, dispatched to rescue them by Irish-American nationalists. When a British steamship caught up to Catalpa, the Catalpa’s captain flew the American flag. The British gave up the chase, not wanting to cause an international incident. The six men made it to the United States intact.

Louis-Napoléon Bonaparte, nephew of Napoleon I, had been serving a life sentence at the Fortress of Ham in northern France for a botched coup attempt. Noticing that maintenance workers were allowed in and out of the fortress without showing any identification, the prince shaved off his mustache, donned a workman’s blue smock, and held a plank of wood over his shoulder to mask his face as he walked past the distracted guards. He escaped to London and eventually returned to France as Emperor Napoleon III. French prisons would thereafter require all civilian workers to have a registry and gate pass.

In 1863, Confederate cavalry general John Hunt Morgan was locked up in the Ohio State Penitentiary, a civilian prison in Columbus, after his foray into Indiana and Ohio during the Civil War. Morgan and six of his men used sharpened mess-hall butter knives to chip away at the floors of their cell until they reached an unmapped ventilation shaft. They then broke out through an outer wall, climbed down ropes braided from bed covers, and caught a train back to Confederate lines. Ohio prisons added daily inspections of the shafts, and the army began keeping officers separate from civilian prisoners.

A group of 109 Union Army officers was being held at Libby Prison, a converted tobacco warehouse that the Confederacy was using as a POW camp in Richmond, Virginia. Led by Colonel Thomas Rose, they crawled overnight through a 50-foot tunnel that had been dug from a rat-infested basement into a tobacco yard across the street. It was the largest prison break of the war. 59 of the 109 men made it back to Union lines. 48 were recaptured, and two drowned trying to swim across a river. The Confederate guards promptly bricked up the basement and dug anti-tunneling trenches around the prison.

When John Gerard, an English Jesuit priest, was imprisoned in the Tower in 1597 during Queen Elizabeth I’s purge of Catholic priests, his torturers dislocated his hands while he was on the rack. Despite this injury, Gerard managed to descend a rope thrown over the Tower’s moat and into the arms of awaiting allies, slipping out of the Tower and into the streets below. The breach revealed another problem: the moat itself was not guarded. The Tower responded by beginning to patrol it for the first time at night.

The Florentine sculptor and goldsmith Benvenuto Cellini was incarcerated in the Castel Sant’Angelo by Pope Paul III for stealing the papal jewels. He used his bed sheets to make a rope, loosened his door hinges with a stolen iron bar, and slipped out onto the wall. On the last drop, he fell, breaking his leg and crawling to safety before being recaptured by the guards. From then on, the cell was checked every day, and armed men stood guard on the top of the fortification.

An English noble named Roger Mortimer, who had been sentenced to death by King Edward II for leading an unsuccessful rebellion, escaped the Tower of London by having an accomplice put a sleeping potion in the guards’ wine at a feast. Once the guards passed out, Mortimer dug through his prison’s walls, climbed onto the roof, and descended by rope ladder. From there, he rowed across the Thames to France. Later, Mortimer came back with Edward’s queen, Isabella, and helped unseat King Edward II.

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