The 20 Most Famous Escapes in History

Allied prisoners of war spent months digging tunnels and coordinating supplies in preparation for an escape in March 1944. Seventy-six men managed to escape before the plot was discovered and thwarted. Most were recaptured, and the consequences were dramatic, which partly explains why this event remains so famous.

Colditz was a high-security Nazi prison designed to house repeat offenders who specialized in escape attempts, which virtually guaranteed a constant stream of escape attempts. The prisoners tried disguises, forged documents, secret routes, and a whole series of impressive plans, ranging from the most ingenious to the most daring. Several inmates managed to escape, even though the castle had a reputation for being “impenetrable.” It became famous because the ingenuity never really stopped.

Giacomo Casanova escaped from the famous Plombs Prison in Venice in 1756, where he was being held in one of the cells on the top floor, and later described the escape in detail. His account helped turn this escape into a legend, in part because he wrote like someone who loved being the main character. But, aside from his outsized ego, the prison’s reputation for harshness was very real, and the escape was truly impressive.

George Blake, a British Secret Service agent who was spying for the Soviet Union, escaped from Wormwood Scrubs Prison in London in October 1966. He received help from outside contacts, and the whole affair was very embarrassing for the authorities. After his escape, he fled to the Eastern Bloc and remained out of reach of British authorities for decades.

In June 2015, Richard Matt and David Sweat escaped by digging tunnels through the walls and crawling through the prison’s utility shafts. The ensuing manhunt was massive and lasted several weeks, capturing the public’s attention. One of the escaped inmates was killed during the search, and the other was captured shortly afterward, but the planning behind this escape nonetheless shocked the public. It is a modern example of how effectively prisons can conceal their vulnerabilities.

Joaquín “El Chapo” Guzmán escaped in July 2015 through a tunnel connected to the shower room. Reports describe a tunnel that appeared to have been designed for speed and efficiency, raising serious questions about possible inside complicity. Given that he was a high-profile criminal and his escape was particularly scandalous, the case made international headlines and reignited concerns about corruption and security lapses.

Union officers held at Libby Prison in Richmond dug a tunnel and escaped in February 1864. More than a hundred prisoners fled in the first wave, making it the largest escape of the Civil War. Many still faced a perilous journey and the risk of being recaptured, so their escape was only the first step. This escape is remembered for both its scale and its audacity.

On September 25, 1983, thirty-eight IRA prisoners escaped from Maze Prison, one of the most secure prisons in Europe at the time. The operation required extensive coordination, diversionary tactics, and the use of violence. Its political impact was enormous, and the event caused a sensation far beyond the United Kingdom and Ireland. When people talk about the “greatest” modern escapes in Europe, this one is always mentioned.

In 1971, more than 100 prisoners escaped from the Punta Carretas prison in Montevideo through a tunnel. This escape is famous for its scale and for the organization required to carry it out without the tunnel collapsing immediately. It is also remembered because some of those involved went on to become prominent public figures. Few escapes are both as massive and as historically significant.

The Bastille was stormed in July 1789 during the French Revolution, and the prisoners held there were freed. Although there were only a few prisoners, the event carried enormous symbolic significance, which is why it is still regarded as a historic moment—even though it is less well known as a prison-related event than as the catalyst for a political upheaval.

Winston Churchill escaped from a Boer prisoner-of-war camp in Pretoria in 1899. He fled and traveled undercover, relying on the help of others and his quick thinking to avoid being recaptured. This story helped make him known to the general public long before he became England’s most famous prime minister.

In March 1934, John Dillinger escaped from Crown Point Prison in Indiana in a breakout often linked to a fake gun. The humiliation was immense, as the facility was touted as ultra-secure, yet he still managed to escape. He even stole a sheriff’s car during his escape.

Ronnie Biggs, one of the perpetrators of the famous mail train robbery, escaped from Wandsworth Prison in 1965 with the help of accomplices on the outside. The incident caused a media sensation, as the robbery itself was already famous and the escape added a new dramatic chapter to the story. For years, Biggs remained an iconic figure in popular culture, which helped keep the story alive.

Charlie Wilson, another figure linked to the Great Train Robbery, escaped from prison in 1964 after receiving outside help. This escape reinforced the notion that this group was determined to defy the system at every opportunity.

In 1973, during what was probably the most daring escape ever attempted, a helicopter landed in the exercise yard of Mountjoy Prison in Dublin, allowing the prisoners to escape in an operation that seemed unbelievable even as it was unfolding. This single image made the escape famous, as it seemed like something security should have prevented. It also demonstrated how a daring plan can exploit a location’s routines and blind spots.

During the 1990 riot at Strangeways Prison in Manchester, the chaos allowed some inmates to escape. It was not a meticulous, well-planned escape, but rather a loss of control that created an opportunity. This event became infamous because it highlighted deep-seated problems within the prison system—not just a clever escape.

In 1995, inmates escaped from HM Prison Parkhurst, located on the Isle of Wight, a facility known for housing high-risk prisoners. This escape attracted attention because it revealed security flaws at a facility that was supposed to be extremely difficult to breach. The inmates were recaptured four days later, but the fact that they had managed to escape sparked widespread public concern.

In December 2000, seven inmates escaped from a high-security prison in Texas and remained at large for several weeks. The case caused a major stir because the group committed serious crimes after their escape, triggering a public safety crisis. The manhunt was intense, and the case made headlines for a long time. It is remembered as much for what happened afterward as for the escape itself.

In 1846, Louis-Napoléon Bonaparte, the future Napoleon III, escaped from the fortified prison at Ham, where he was being held following a failed coup. He reportedly used a disguise to escape and avoid immediate capture, and then made his way to safety. After his escape, he returned to politics and became Emperor of the French, which made his feat all the more significant.