The 20 Most Daring Prison Escapes in History

In June 1962, inmates Frank Morris and brothers John and Clarence Anglin pulled off one of the most famous escapes in history. They spent months digging through the walls of their cells and leaving papier-mâché heads in their beds to deceive the guards. After reaching a service corridor, they escaped using a makeshift raft made from raincoats.

During World War II, Allied prisoners at the German camp Stalag Luft III organized a mass escape attempt in March 1944. The prisoners secretly dug a 102-meter tunnel under the camp and planned to help hundreds of them escape.

During World War II, Colditz Castle in Germany held Allied officers considered particularly likely to attempt an escape. Despite the castle’s heightened security and its location on a cliff, the prisoners constantly devised new escape plans. Over time, dozens of prisoners managed to escape, proving that the fortress was not as secure as previously thought.

In 1934, the famous American bank robber John Dillinger escaped from Crown Point Prison in Indiana using a wooden pistol he had carved himself. He reportedly painted this fake gun black to make it look more realistic. Dillinger used it to intimidate the guards and lock them in their cells before making his escape.

Billy Hayes, an American who was imprisoned in Turkey for drug trafficking in the 1970s, made a dramatic escape from Imralı Prison. After several years behind bars, he disguised himself and managed to reach a small boat on the island where the prison was located.

In Northern Ireland, 38 prisoners at Maze Prison carried out one of the largest prison breaks in British history. Members of the Irish Republican Army used weapons that had been smuggled in and took several guards hostage. They hijacked a prison supply truck and drove through the prison gates.

French criminal Pascal Payet became famous for escaping from prison by helicopter—not once, but twice. In 2001, accomplices hijacked a helicopter and landed in the courtyard of a French prison to pick him up. He was later recaptured, but in 2007, another helicopter came to rescue him from a maximum-security prison.

Psychologist Timothy Leary, known for his advocacy of psychedelic drugs, escaped from a California prison in 1970. Members of the Weather Underground helped him organize his escape after he climbed over the prison fence.

Mexican drug lord Joaquín “El Chapo” Guzmán escaped from a high-security prison in 2015 through a tunnel dug beneath his cell. The underground passage, more than one and a half kilometers long, was equipped with a lighting and ventilation system. Guzmán had vanished before the authorities even realized what had happened.

Long before the advent of modern prisons, the Venetian adventurer Giacomo Casanova pulled off a remarkable escape from the prison in the Doge’s Palace in 1756. After months of preparation, he and another prisoner managed to break through the roof of their cell.

In December 2000, seven inmates escaped from the John B. Connally Unit prison in Texas. They overpowered the guards and hid in a maintenance area before leaving the premises in a stolen vehicle. The group remained on the run for several weeks, attracting nationwide attention.

Henri Charrière, often nicknamed “Papillon,” claimed to have escaped from the French penal colony in French Guiana. According to his memoirs, he used a raft made of coconuts to cross the treacherous waters.

American bank robber Willie Sutton became famous for escaping from prison several times. During a memorable escape in the 1940s, he disguised himself as a prison guard and simply walked out of the facility.

Serial killer Ted Bundy escaped from prison in Colorado twice in the 1970s. The first time, he jumped out of a courtroom window while representing himself. Later that year, he slipped through a small opening in the ceiling of his cell.

Frank Abagnale Jr., known for impersonating airline pilots and other professionals, escaped from prison in the United States in the 1960s. He managed to evade the guards by posing as a member of the flight crew.

During the Vietnam War, U.S. Navy pilot Dieter Dengler was captured and held in a prisoner-of-war camp deep in the jungle of Laos. After months of planning, he and several other prisoners overpowered their guards. Dengler fled into the dense jungle and survived for several days under harsh conditions before being rescued.

Jack Sheppard was an English thief in the early 18th century who became famous for escaping from prison on several occasions. The authorities captured him several times, but he always found new ways to escape.

During the American Civil War, Union officers held at Libby Prison in Richmond staged a meticulously planned escape in 1864. They secretly dug a tunnel from inside a storage room located beneath the prison. More than a hundred prisoners crawled through the tunnel to regain their freedom.

Brazilian prisoner José Carlos dos Reis Encina made a surprising escape from prison in the 1980s. He reportedly switched places with a family member who had come to visit him and who looked just like him. The guards did not notice the switch at first, which allowed him to leave the prison.

Before the famous escape in 1962, other inmates had attempted to escape from Alcatraz despite the dangerous waters surrounding it. In 1937, Theodore Cole and Ralph Roe managed to escape from the prison workshop.