Even the world’s most secure prisons have seen their fair share of cunning criminals launch escape attempts. In the 18th century, for example, William Maxwell strolled out of the Tower of London disguised as a woman. Centuries later, in 1934, bank robber John Dillinger whittled a fake gun out of wood and used it to force his way out of Indiana’s Crown Point Jail.
Whether prisoners have escaped using brute force, cunning or sheer dogged determination, prison breaks have long captured the public imagination.
Here are 5 of the most audacious prison escapes in history.
1. William Maxwell – Tower of London (1716)
In 1715, Scottish nobleman and 5th Earl of Nithsdale William Maxwell was found guilty of treason, having participated in the 1715 Jacobite Rebellion. He was thrown in the Tower of London and ultimately sentenced to death.
The day before Maxwell’s planned execution in 1716, his wife Winifred visited him at the tower. Winifred and some of her companions were granted access to his cell, where they delivered him a smuggled petticoat and a woman’s cloak.
Donning the clothes and posing as a woman, Maxwell strolled out of the Tower of London and managed to sail out of England. He then posed as an Austrian ambassador’s servant, reaching Italy. Winifred, suspected of aiding her husband’s escape, also fled England, and the pair reunited as exiles in Rome.
2. Mass breakout – Libby Prison (1864)
During the American Civil War, the Confederates converted an old warehouse in Richmond, Virginia, into the Libby Prison. Used to house prisoners of war, the facility became hugely overcrowded and rife with disease.
In 1863, a band of prisoners began secretly tunnelling below the prison. After three failed attempts, they managed to dig a successful tunnel outside of the facility. It was some 50 feet long, as narrow as 40cm at times and infested with rats.
Using the tunnel, 109 prisoners escaped Libby Prison, making a break for Union lands. Of those that fled, 59 successfully made it to Union territory, 48 were captured and 2 drowned in the James River. Many of the successful escapees used the North Star to navigate their way out of Confederate lands.
3. John Dillinger – Crown Point County Jail (1934)
Bank robber John Dillinger earned notoriety for evading capture and escaping police custody on several occasions in the 1930s.
In 1933, Dillinger committed a string of high-profile bank robberies and was ultimately arrested. He was then broken out of jail in Lima, Ohio, by way of brute force: his associates initially tried to gain access to him by posing as police officers, but when asked for their badges they shot and killed the sheriff on duty and released Dillinger.
The law caught up with Dillinger in January 1934. He was sent to Indiana to face charges for his involvement in a Chicago bank heist during which a patrolman was murdered.
On 3 March 1934, Dillinger escaped the Crown Point County Jail by threatening guards with a fake gun – thought to have been made by Dillinger himself by carving a washboard into the shape of a firearm using a razor blade. He stole a car and fled the area, but was shot a few months later by FBI agents in Chicago.
4. Clarence Anglin, John Anglin and Frank Morris – Alcatraz (1962)
Nicknamed ‘The Rock’, Alcatraz is a famed former penitentiary housed on a small island off the coast of San Francisco. During its 29 years in operation, the prison faced around 14 escape attempts.
In June 1962, three prisoners – Frank Morris and brothers Clarence and John Anglin – put a long-planned prison break into action. They had spent weeks digging away at the ventilation holes in their cell walls to make them wide enough to crawl through. They fled through the holes and into the prison’s ventilation shafts, leaving dummies in their beds to avoid arousing suspicion.
Arriving at the island’s edge, the three men built a makeshift raft out of contact cement and raincoats. The escapees were never heard of again, and a wide-scale manhunt revealed no sign of them. It’s presumed that the three fugitives drowned trying to cross the San Francisco Bay.
5. El Chapo – Altiplano (2015)
Joaquin Guzman Loera, better known as ‘El Chapo’, was a notorious Mexican drug trafficker and leader of the Sinaloa cartel. He has escaped from two separate high-security Mexican prisons.
El Chapo was arrested in 1993 and sentenced to 20 years imprisonment in Mexico. He paid off many of the prison staff in exchange for privileges and continued to run his criminal enterprise from inside prison.
In 2001, Chapo made his first jailbreak, thought to have been wheeled out of the prison in a laundry cart by a guard. El Chapo remained at large until 2014, when he was recaptured and sent to Altiplano prison, the highest security penitentiary in Mexico.
On 11 July 2015, El Chapo escaped Altiplano. He slipped through a hole under the shower of his cell and fled through a tunnel – fitted with lighting and ventilation – that had been dug by his associates. Eventually, law enforcement officials caught up with him in 2016.