8 Daring Prison Breaks in History

On June 12, 1962, inmates Frank Morris, John Anglin, and Clarence Anglin are discovered missing from their cells on Alcatraz Island during an early morning bed check. To this day, they have never been found. It is the most iconic prison escape in American history.

Take a look at a list of history’s other daring prison breaks:

1. Catholic Nobleman Who Fled in Drag (1716)
William Maxwell, 5th Earl of Nithsdale (1676 – March 2, 1744) was a Catholic nobleman who took part in the Jacobite Rising of 1715. After joining the rebellion, the earl was captured at Preston together with other Jacobite leaders. He was found guilty of treason, sentenced to death, and locked in the Tower of London. On February 24, 1716, the night before the day of his execution, his wife Lady Nithsdale went to visit him in prison accompanied by her maid and friends. The group smuggled in women’s clothes for the Earl then spirited him out of the Tower disguised as a woman. The Earl fled to Rome where he lived with his wife until his death.

2. Public Enemy No.1 and His Fake Wooden Gun (1933)
In the heyday of the Depression-era outlaw, John Herbert Dillinger (June 22, 1903 – July 22, 1934) was one of the most wanted American gangsters. After spending most of his 20s in state prison for attempting to hold up a small-town Indiana grocer, Dillinger was paroled in May 1933. From September 1933 until July 1934, he and his violent gang terrorized the Midwest. They killed 10 men, wounded 7 others, robbed banks and police arsenals, and staged 3 jail breaks – killing a sheriff during one and wounding 2 guards in another. Of his 3 jail breaks, Dillinger’s March 3, 1934 escape from the Lake County Jail in Crown Point, Indiana was the most infamous as the the jail was deemed “escape-proof”. Originally arrested on charges that he killed a police officer during a bank robbery in 1933, he allegedly used a fake gun carved out of wood and blacked with shoe polish to escape.

3. Catch Me if You Can (1971)
Between the ages of 15 and 21, Frank William Abagnale Jr. (born April 27, 1948) spent his years posing as a check forger, teacher, doctor, attorney, and faux airline pilot and so on. He was eventually captured in France in 1969, and served six months in a French prison, six more in Sweden, finally being deported to the United States where he was sentenced an additional 12 years in the federal prison. Abagnale attempted to escape from the Federal Detention Center in Atlanta Georgia in 1971 by convincing the prison guards that he was a prison inspector. Despite the 1971 escape attempt and another one, Abagnale was paroled after five years on the condition he would help federal authorities uncover check forges. Abagnale parlayed his unique skills into a security consultant career advising banks and businesses on how to avoid fraud. Abagnale’s early life story inspired the feature film Catch Me If You Can starring Leonardo DiCaprio.

4. The Serial Killer Who Fled Up in Aspen (1977)
Nobody knows when or where Theodore “Ted” Robert Bundy (born Theodore Robert Cowell; November 24, 1946 –January 24, 1989) killed for the first time. According to the FBI, Bundy’s prolific reign of terror and murder was well underway by 1974. In 1976, law school dropout Bundy was charged with killing a vacationing nursing student, and he found himself in Aspen, Colorado in June 1977 for a preliminary hearing. Bundy, who was acting as his own attorney, asked to use the court’s law library, was left alone there, and jumped out of a second-floor window then fled up Aspen Mountain. Bundy was located in Aspen a few days later. On New Year’s Eve in 1977, after losing weight, Bundy seized another opportunity for escape and slipped through an opening in the ceiling of his cell, walked out of the front door through the jailer’s office. Bundy continued his murder spree while on the run. On the evening of January 14, 1978, he invaded a Florida State University sorority house and brutally killed two co-eds and left a third with serious injuries. Bundy was apprehended by police in Pensacola on February 15, 1978. He received three death sentences in two separate trials for the Florida homicides, and died in the electric chair at Raiford Prison in Starke, Florida on January 24, 1989. Shortly before his execution, he confessed to 30 homicides committed in seven states between 1974 and 1978. Some experts have suggested the actual number might be higher.

5. The Flying Murderer (2001, 2003, 2007)
A French convicted killer Pascal Payet (born July 7, 1963) fled into the sky in a helicopter not just once, but three times. He was initially sentenced to a 30-year jail term for a murder committed during the robbery of a security van in 1997. Payet’s first escape came in 2001 when he arranged for friends to collect him from the roof of a village prison in a helicopter. Two years later, while still a fugitive, he re-visited the same prison to help three more inmates escape by chopper. He was eventually caught, but then escaped for the third time from the Grasse prison in southeast France in 2007 using a helicopter hijacked by four men in Cannes. Payet and his accomplice fled, and the pilot was not harmed. Payet was recaptured on September 21, 2007 in Barcelona, Spain and was transferred to French custody a couple of weeks later.

6. Korean Houdini (2012)
Choi Gap-bok, 50, a yoga practitioner for 23 years, was arrested on suspicion of robbery on September 12, 2012, and was put in a detention cell at the police station in Daegu, South Korea. On early morning on September 17, while his prison guards were asleep, Choi applied the “special cream” he had requested on the upper part of his body and slipped out of the food slot at the bottom of his cell. The space that the 5’4’ Choi squeezed through was 5.9 inches tall and 17.7 inches wide. The escape only took 34 seconds. Six days later, Choi was caught and put in a cell with a much smaller food slot.

7. NY Prison Break (2015)
On June 6, 2015, for the first time in the 170-year old history of the Clinton Correctional Facility in New York, convicted killers David Sweat, 34, and Richard Matt, 48, vanished from the maximum security prison leaving guards a note that read “have a nice day”. They smuggled in hacksaw blades, hiding them in frozen hamburger meat, and cut through a steel wall, carved into a large pipe and crawled along tunnels before finally popping out of a manhole in Dannemora, New York. Their expected ride never showed up, and after 20 days on the run, Matt was shot dead while Sweat was returned to custody two days later.

8. Mexican Drug Lord (2015)
Mexico’s most notorious drug lord, Joaquín Guzmán Loera (born December 25, 1954 or April 4 1957), known as El Chapo, escaped from a high-security prison in a laundry cart in 2001. It took authorities 13 years to catch him again. After only 17 months back in prison, on July 11, 2015, Guzmán, the billionaire head of the powerful Sinaloa Cartel, stepped into a shower at a maximum-security prison, crawled through a hole and vanished through a mile-long tunnel apparently built for him. The tunnel began with a 20×20 inch opening inside the shower of Guzmán’s cell. The Mexican prison from which El Chapo escaped is virtually identical in layout to one he escaped in 2001. Guzmán was recaptured by Mexican marines following a shootout on January 8, 2016.

Secrets of the Dead: The Alcatraz Escape, premieres nationally Tuesday, March 29 at 9 p.m. on PBS (check local listings).