1. The inmates who fled The Rock in a raft made from raincoats

Alcatraz Island Prison seen from above.
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The notorious penitentiary on Alcatraz Island.

From 1934 to 1963, the U.S. penitentiary on Alcatraz Island in the middle of San Francisco Bay housed some of America’s most notorious criminals, including Al Capone, George “Machine Gun” Kelly and James “Whitey” Bulger. During its 29 years as a federal prison, approximately 1,545 men did time at the maximum-security facility, nicknamed The Rock, and there were 14 different escape attempts involving 36 inmates. The most celebrated escape attempt took place in June 1962, when three prisoners fled the island on a raft constructed from raincoats. In the months leading up to their daring escape, the men had used homemade tools to slowly widen the ventilation holes in the walls of their cells, which they crawled through on the night they vanished. In their beds, they left lifelike dummy heads they’d devised as decoys. Despite a lengthy, large-scale manhunt, the fugitives never were heard from again and authorities believe they likely drowned in the San Francisco Bay’s strong, cold currents. Clint Eastwood starred in a 1979 movie about the breakout, fittingly titled “Escape from Alcatraz.”

Of all the prisoners who attempted to flee Alcatraz, 23 were captured, six were shot and killed while trying to escape and two drowned. An additional five (including the three who broke out in 1962) remain unaccounted for and are presumed drowned.

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2. The Union POWs who tunneled out of a Confederate prison

Libby Prison in Richmond, Virginia, circa 1865.
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Libby Prison in Richmond, Virginia, circa 1865.

On February 9, 1864, 109 Union officers tunneled their way out of Libby Prison, a bleak, Confederate prisoner-of-war facility in Richmond, Virginia. After opening in March 1962, the prison, situated in a former tobacco warehouse, quickly became an overcrowded, disease-ridden place where prisoners were subjected to severe food shortages. Starting in the fall of 1863, a small group of inmates made three failed attempts to dig tunnels out of the prison. With rats crawling over them as they labored in secret, the men finally managed to dig a fourth tunnel—measuring 50 feet long and ranging in width from 36 to 16 inches—that they used to escape. Fifty-nine of the men eventually reached Union territory, while 48 were recaptured and two drowned. Following the Libby Prison escape, Confederate officials transferred most of the prisoners there to other sites, including the notorious POW camp at Andersonville, Georgia.

3. Britain’s Biggest Prison Break

A watchtower and perimeter wall marks the boundary of the former Maze Prison, west of Belfast in Northern Ireland.  (Credit: Paul Mcerlane/Getty Images)
Paul Mcerlane/Getty Images
A watchtower and perimeter wall marks the boundary of the former Maze Prison, west of Belfast in Northern Ireland.

The largest prison escape in British history took place on September 25, 1983, when 38 inmates, all of them members of the Irish Republican Army, broke out of Her Majesty’s Prison Maze near Belfast, Northern Ireland. Opened in 1971, the maximum-security facility housed a number of men convicted of crimes linked to the Troubles, the conflict between unionists who wanted Northern Ireland to remain part of the United Kingdom and republicans who favored the unification of Ireland. In 1981, a group of Irish republicans at Maze Prison launched a hunger strike; 10 died, including their leader, Bobby Sands. 

The 1983 escape occurred after inmates, armed with smuggled guns and knives, overpowered guards and hijacked a truck delivering food to the prison. Prison officers tried to block the vehicle from getting past the gate, forcing the escapees to jump from the back of the vehicle and run. One guard was stabbed during the escape and died of a heart attack, while nearly two dozen other prison officers were injured. Within a few days, 19 of the men were caught (three others never made it off the prison grounds) but the others got away. Several of the men eventually made it to the United States. The Maze prison was closed in 2000 as part of the 1998 Good Friday peace accord.

4. The notorious drug kingpin who escaped–twice

Drug trafficker Joaquin "El Chapo" Guzman is escorted to a helicopter by Mexican security forces. (Credit: Susana Gonzalez/Getty Images)
Susana Gonzales/Getty Images
Drug trafficker Joaquin “El Chapo” Guzman is escorted to a helicopter by Mexican security forces.

On February 22, 2014, one of the world’s most-wanted criminals, drug trafficker Joaquin “El Chapo” (“Shorty”) Guzman Loera, was arrested after outrunning law enforcement for more than a decade. Guzman, a third-grade dropout, was first arrested in 1993 and sentenced to 20 years behind bars for murder. While locked up in a high-security prison in the Mexican state of Jalisco, he paid off the staff and continued to run his criminal enterprise. In 2001, he escaped the facility; some accounts claim Guzman was wheeled out in a laundry cart, while other sources suggest prison officials simply let him walk out. For years afterward, he used violence, bribery and a large network of informants to help him remain a fugitive. His cartel grew into the largest supplier of illegal narcotics to America, and the U.S. government offered a $5 million reward for information leading to his arrest.

On February 22, 2014, law enforcement agents finally tracked down the drug kingpin to an apartment in Mazatlán, Mexico, and arrested him. However, on July 11, 2015, Guzman, then incarcerated at the nation’s highest-security penitentiary, Altiplano, approximately 55 miles west of Mexico City, once again escaped, this time via a hole in the floor of his cell and out through a mile-long tunnel that had been secretly dug and equipped with lights and ventilation. Guzman was re-captured by Mexican authorities in 2016.

5. The famous gangster who got out of jail with a fake gun

Portrait of American criminal gang leader and bank robber John Dillinger.  (Credit: American Stock/Getty Images)
American Stock/Getty Images
Portrait of American criminal gang leader and bank robber John Dillinger.

After spending most of his 20s in state prison for attempting to hold up a small-town Indiana grocer, John Dillinger was paroled in May 1933 and went on to pull off a string of bank robberies that turned him into one of America’s most-wanted gangsters. In September 1933, he was arrested in connection with a bank heist and jailed in Lima, Ohio. The following month, several of Dillinger’s criminal associates showed up at the Lima jail and posed as law enforcement officials, informing the sheriff they wanted to see Dillinger. When the sheriff asked to look at the men’s badges, they killed him then sprung Dillinger from his cell. In January 1934, while Dillinger and some accomplices were holding up a bank in East Chicago, Indiana, a police officer was shot and killed. Dillinger was apprehended later that month in Tucson, Arizona. 

Afterward, he was extradited to Indiana to stand trial for the East Chicago murder and held at the county jail in Crown Point, a facility authorities had bragged was escape-proof. However, on March 3, 1934, Dillinger, armed with a fake gun (either smuggled in by his attorney or made by Dillinger himself), forced guards to release him, stole a sheriff’s car and escaped. That July, FBI agents finally caught up with the 31-year-old gangster and shot him dead as he was leaving a movie theater in Chicago.

6. The nobleman who fled the Tower of London in drag

After joining the Jacobite rebellion of 1715, Catholic nobleman William Maxwell, 5th Earl of Nithsdale, was locked up in the Tower of London, found guilty of treason and sentenced to die. Shortly before she believed her husband was to be executed, Lady Nithsdale went to visit him in prison in 1716, accompanied by her maid and several female friends. The group smuggled in women’s clothing for the earl then spirited him out of the Tower of London disguised as a member of the fairer sex. The earl fled England, this time masquerading as a servant to a Venetian ambassador, and ended up in Rome. Lady Nithsdale’s own life was in danger once her involvement in the earl’s escape was suspected, but she managed to flee Britain separately and meet her husband in Rome, where they resided in exile.

7. The serial killer who went on the lam in the Rockies

FBI wanted poster for Ted Bundy. (Credit: Universal History Archive/Getty Images)
Universal History Archive/Getty Images
FBI wanted poster for Ted Bundy.

In 1976, law school dropout Ted Bundy began serving time in a Utah prison for a kidnapping conviction. The following year, he was extradited to Aspen, Colorado, to stand trial for the 1975 murder of a nurse. During a recess at a courthouse hearing in June 1977, Bundy, who was acting as his own attorney, asked to use the court’s law library. Left alone there, he jumped out of a second-floor window and then fled up Aspen Mountain. During the six days he was on the lam, Bundy got lost, stole a car and returned to Aspen, where he was caught by police. He was returned to the county jail in Glenwood Springs, 40 miles away. In December, after losing weight, Bundy was able to squeeze through a hole made for a light fixture in the ceiling of his cell, move through a crawl space, drop down into a jailkeeper’s apartment and walk out the front door. From there, he made his way to Florida, where he murdered two female Florida State University students and a 12-year-old girl. Bundy was apprehended by police in Pensacola on February 15, 1978. Before he was put to death in the electric chair in 1989 at age 42, Bundy confessed to 30 murders around the U.S.; some experts have suggested the actual number might be higher.

8. The WWII Prison Escape That Almost Took Flight

Colditz Castle. (Credit: Michael DeFreitas/Getty Images)
Michael DeFreitas/Getty Images
Colditz Castle.

During World War II, Colditz Castle, an ancient fortress in eastern Germany, was converted into a high-security POW camp. Many of the men incarcerated in the castle, officially known during the war as Oflag IV-C, had been sent there because they’d previously escaped, or attempted to escape, from other POW camps. A number of prisoners tried to break out of Colditz, some of them successfully; those who were caught typically were punished with a stint in solitary confinement. However, after the Nazis executed 50 POWs who’d tried to flee Stalag Luft III in March 1944 (an event that came to be referred to as the Great Escape), British military intelligence warned against further prison breaks. That didn’t stop a small group of men at Colditz from working on a unique escape plan: the construction of a glider plane. The group, which included British pilots Bill Goldfinch and Jack Best, along with Tony Rolt, a former race car driver, worked in a hidden space in an attic and built the two-person glider using stolen pieces of wood and electrical cable. The men intended to launch the glider, dubbed the Colditz Cock, from the castle roof. Before that happened, though, Colditz was liberated by the Allies in April 1945. In 2000, a full-size replica of the Colditz Cock was constructed based on Goldfinch’s original specifications and flown at a Royal Air Force station in England, with Goldfinch, Best and other veterans in attendance.