The Most Ridiculous (And Real) Prison Escapes of All Time

These stories sound like the stuff of Hollywood screenplays, but they're all true.

July 12, 2018 9:00 am
prison escapes
5th February 1934: American criminal John Dillinger sits handcuffed to Deputy Chief Carroll Holby, beside his attorney Joseph Ryan while on trial in Crown Point, Indiana. (American Stock/Getty Images)
Getty Images

Prison breaks are a popular Hollywood trope to free the hero or ID a villain, but some of the wildest stories aren’t scripted. Real-life prison escapes are even more intense than what we see in the movies. Some prisoners even manage multiple escapes, through means as varied as dug-out tunnels to fake wooden guns to utilizing friends (and helicopters). Check out the gallery below to learn about more about the most foolhardy prison escapes in history.

Escape from Alcatraz

A prison guard kneels by hole in Frank Morris cell through which he and John and Clarence Anglin escaped. Prison officials report hole was dug with broken spoons.; (The Denver Post via Getty Images)
Denver Post via Getty Images

You would think it would be impossible to break out of Alcatraz, but on June 11, 1962, lifetime criminals Frank Lee Morris and brothers John and Clarence Anglin escaped from “The Rock” through a hand-dug tunnel. The trio had made fake heads out of soap, toilet paper and real hair, which tricked guards during their night-time inspections. They’d spent the last year using crude tools to carefully dig a tunnel in their adjacent cell walls that led to an unused service corridor. From there, they climbed a ventilation shaft to the roof. They scaled a fence and assembled a raft out of raincoats and contact cement they had stolen from the prison. They were not discovered missing until the next morning. Much to the horror of locals, the FBI never found a trace of them on the island or nearby Angel Island, and it was feared they could be living under the radar among the population. Seventeen years later, the FBI concluded their investigation, saying the three men must have drowned in the bay.

French Lovers

Michel Vaujour and his lawyer. (Jean-Michel TURPIN/Gamma-Rapho via Getty Images)
Gamma-Rapho via Getty Images

Nadine Vaujour wanted her husband out of prison, so she decided to take helicopter lessons in order to help him escape. Michel Vaujour was serving a long sentence for attempted murder and armed robbery. In May 1986, he used nectarines that were painted to look like grenades to force his way onto the prison’s roof. His wife then picked him up in a helicopter and they flew to a football field, where a car was waiting and they drove away. But Nadine Vaujour was discovered and arrested. Michel survived being shot in the head during a failed bank robbery.

Another Flying Criminal

Pascal Payet (Wikipedia)

It appears helicopters are a popular method of prison escape. French murderer Pascal Payet gained international notoriety for his role in a series of prison breaks that included helicopters, beginning in 2001 when his friends used one to collect him from the roof of the village prison. Two years later, he repeated that scene to help three more prisoners escape. He was later caught and sentenced to 30 years in prison for murder. He managed to break out of the closely guarded prison in 2007 when masked men hijacked a helicopter and jumped out of it at the prison with sawed-off shotguns, blasted their way in and came out with Payet. He was caught, again, months later in Barcelona and is now in prison in an undisclosed location.

John Dillinger Uses a Wooden Gun

5th February 1934: American criminal John Dillinger sits handcuffed to Deputy Chief Carroll Holby, beside his attorney Joseph Ryan while on trial in Crown Point, Indiana. (American Stock/Getty Images)
Getty Images
Viewers outside the prison from the John Herbert Dillinger (American gangster and bank robber) escaped. About 1933. Photograph. (Imagno/Getty Images)
Getty Images

John Herbert Dillinger was America’s public enemy No. 1 when he went on a yearlong crime spree across the midwest. He and his gang reportedly robbed a dozen or so banks and police stations, killing 10 men in the process. He was finally arrested in Tucson, Arizona in January 1934 and put in Lake Country Jail in Crown Point, Indiana. But in March 3, 1934, Dillinger and another inmate allegedly used a fake gun carved out of wood and blackened with shoe polish to force their way out of the facility. He then escaped in the sheriff’s brand-new V-8 Ford. FBI agents found and killed Dillinger later that year in Chicago.

The Texas 7

This composite of images taken 02 January, 2001 from the Texas Department of Criminal Justice Internet site shows seven prisoners who escaped 13 December, 2000 from a Texas maximum-security prison in Kenedy, Texas, about 60 miles southeast of San Antonio. The fugitives (top L-R) Joseph Garcia, Donald Newbury, George Rivas, Larry Harper, (bottom L-R) Patrick Murphy, Jr., Randy Halprin and Michael Rodriguez had been serving sentences ranging from 30 years to life and allegedly escaped by posing as prison workers. The men are also wanted in connection with a Christmas Eve robbery of a Dallas-area sporting goods store in which a policeman was shot and killed. (TDCJ/AFP/Getty Images)
AFP/Getty Images

This was the biggest prison break in Texas history. In 2001, seven prisoners forced their way out of maximum security prison John B. Connally Unit in the isolated town of Kenedy. Their leader was George Rivas, who was serving 18 consecutive life sentences for burglary and kidnapping. Seven men (including two convicted murderers) overpowered two guards and eight maintenance men and stole their clothes and keys, locking them in a utility closet and then fooling several other guards in order to take weapons and flee in a truck. The Texas 7 then went on a crime spree from San Antonio to Dallas and into Colorado. They were eventually captured, but not before killing 29-year-old police officer Aubrey Hawkins in Texas. One of the seven inmates killed himself before being captured, but the other six were taken back to John B. Connally Unit. Of these, three have been executed, including Rivas.

 Not Just Once, But Twice

Joaquin Guzman Loera, also known as ‘El Chapo’ is transported to Maximum Security Prison of El Altiplano in Mexico City, Mexico on January 08, 2016. Guzman Loera, leader of Mexico’s Sinaloa drug Cartel, was considered the Mexican most-wanted drug lord. Mexican marines captured ‘El Chapo’ on Friday in Sinaloa, North of Mexico. (Photo by Daniel Cardenas/Anadolu Agency/Getty Images)
A view of the tunnel through which according to the authorities Joaquin ‘El Chapo’ Guzman escaped from Mexican Maximum Security Prison of ‘El Altiplano’ on July 15, 2015 in Mexico City, Mexico. ‘El Chapo’ escaped through a tunnel made between the prison and a half-built house, according to the Government’s version, making this the second time he escapes from a maximum security prison. (Manuel Velasquez/LatinContent/Getty Images)
LatinContent/Getty Images

Joaquin “El Chapo” Guzman, Mexico’s most notorious drug lord, escaped from a high-security prison in a laundry cart in 2011, with the help of bribed guards. One guard opened the door to El Chapo’s cell while the other helped him climb into the cart. They pushed him outside, and once there, he hopped into the trunk of a Chevrolet Monte Carlo. It took authorities 13 years to catch him. But he didn’t stay behind bars for long: after only 17 months back in prison, Guzman stepped into the shower of a maximum security prison and crawled to freedom through a mile-long tunnel that was built just for him. The tunnel was complete with lighting, ventilation and even a modified motorcycle on tracks that was probably used to transport tools for the dig. El Chapo was caught in January 2016 and is now held in the United States.

Escape Artist

Alfie Hinds (Wikipedia)

“Alfie” Hinds was a British criminal and escape artist who successfully broke out of three high security prisons while serving a 12-year sentence for robbery. He taught himself law and argued his cases in 17 court appearances, eventually gaining himself a pardon. But first, in 1955, he escaped by copying a key to the jail workshop after memorizing its shape. He was capture eight months later in Ireland. But then he escaped while at a court in London in 1957 when two guards led him to the bathroom. He broke out of prison yet again in 1958 by making a key to a bathhouse.

Hacksaws and Hamburgers

In this handout from New York State Police, convicted murderers David Sweat (L) and Richard Matt are shown in this composite image. Matt, 48, and Sweat, 34, escaped from the maximum security prison June 6, 2015 using power tools and going through a manhole. (Photo by New York State Police via Getty Images)
Getty Images
Joyce Mitchell (L) , a prison worker who allegedly helped two convicts escape from prison, is lead from Plattsburgh Ciy Court after a hearing on June 15, 2015 in Plattsburgh, New York. The convicts, Richard Matt and David Sweat, escaped sometime during the night between June 5 and June 6 from the Clinton Correctional Facility in Dannemora, New York and law enforcement are on a multi-state manhunt for their capture. (Andrew Burton/Getty Images)
Getty Images

Convicted killers David Sweat and Richard Matt did something in 2015 that no one else had done in 170 years: escape from the Clinton Correction Facility, New York state’s largest prison. In order to escape, they carved into a large pipe and worked through a maze of tunnels before popping out of a manhole in Dannemora, New York. They got the tools to break out thanks to Joyce Mitchell, the prison tailor, who admitted to smuggling hacksaw blades by hiding them in frozen hamburger meat. The criminals supposedly left guards a note that read “Have a nice day.” But the duo didn’t get very lucky. Their ride never showed, and about a week into living life on the run, both were shot. Matt died, while Sweat was wounded and captured.

Catch Me If You Can

Frank Abagnale speaks onstage at Catch Me If You Can: Frank Abagnale 10 Years Later during the 2012 SXSW Music, Film + Interactive Festival at Austin Convention Center on March 10, 2012 in Austin, Texas. (Bobby Longoria/WireImage)

Leonardo DiCaprio does a great job in the 2002 film, but the real-life Frank Abagnale was also impressive. He successfully committed a series of incredibly bold crimes, including flying over 1,000,000 miles between the ages of 16 and 18 by impersonating a Pan Am cockpit.  After being sentenced to 12 years in prison in the U.S., Abagnale was transported to a detention facility by a Marshall who had forgotten his papers. Abagnale used the opportunity to convince the guards that he was actually an undercover prison inspector. This was a common method used to test jails at the time, so the guards believed the con man. While inside, he used the help of his friend, who he calls Jean Sebring. Sebring created two business cards, one an FBI agent’s and another a prison inspector’s, and smuggled them into the prison to Abagnale, who then told guards he needed to speak to the FBI agent. The guards called the number on the card, and Sebring picked up. She told the guards she needed to meet Abagnale outside the prison. The guards let him walk right out the front door.

Bent Out of Shape

Choi Gap-bok (YouTube)

Choi Gap-bok bent himself out of shape in order to slip through the tiny slot at the bottom of the cell that is used to give prisoners food. The prisoner had practiced yoga for 23 years and was arrested on suspicion of robbery. He was there for five days before he applied skin ointment and slipped out. The whole escape took only 34 seconds. The space was 5.9 inches tall and 17.7 inches wide. The prison guards were sleeping while Choi wiggled through. He was rearrested six days later.

The Hero Escapee

Alfred Wetzler (Wikipedia)
Entrance gate with the inscription Arbeit macht frei (Work makes you free), Auschwitz concentration camp (Unesco World Heritage List, 1979), Poland.
De Agostini via Getty Images

Everyone else on this list is a convicted or accused criminal, but Alfréd Wetzler was neither of those things. Wetzler was a Slovakian Jew who was sent to the Nazi death camp Auschwitz during World War II. Wetzler and fellow prisoner Rudolf Vrba escaped the death camp in April 1944 by hiding in a wood pile that other inmates had soaked with tobacco and gasoline to fool guards and dogs. They hid for four nights, then donned stolen suits and overcoats and began an 80 mile journey to the Polish border with Slovakia. Wetzler carried a report of the inner workings of the concentration camp, including a ground plan, details of the gas chamber and a label from a canister of Zyklon B, the gas the Nazis were using to kill prisoners. It was the first detailed report that the Allies regarded as credible, and helped lead to the bombing of buildings that housed Nazi officials who dealt with the railway deportations. It is saved that because of this, 12,000 Hungarian Jews were saved.

The InsideHook Newsletter.

News, advice and insights for the most interesting person in the room.