10 Craziest Jail Breaks of All Time

From Michael Scofield’s cunning tactics in Prison Break to Andy Dufresne’s agonizing sewage-pipe crawl in The Shawshank Redemption, prison escapes strike the imagination, especially when the escape is extraordinarily audacious or ingenious.

Both Scofield and Dufresne’s escapes contained multi-layered storylines that forced the spectator to suspend disbelief. Yet, they pale in comparison to some of the most insane jailbreaks that have occurred in real life.

When thousands of frequently desperate individuals are locked away together with plenty of free time, they devise novel solutions to their captivity, which seldom entail hunkering down and behaving.


Stalag Luft III

Roger Bushell led a group of captured soldiers on an escape effort from a German POW camp that would go down in history as one of the most daring, but also one of the most heartbreaking.

Bushell’s plan involved burrowing three deep tunnels, designated Tom, Dick, and Harry, beneath their captors’ noses. These weren’t just ordinary tunnels; they had their own air supply, electrical lights connected to the camp’s grid, and rail car systems for moving commodities from one end to the other.

The tunnels under Stalag Luft III were started in January 1943, and Harry was finished by March of the following year. The camp’s occupants packed in on a moonless night, only to discover that the tunnel was too short. Instead of reaching a nearby forest, the exit was right in front of the enemy.

For most of the escapees, freedom was short-lived. Fifty people were slain, others were taken back to the camp, and only three people managed to escape.

Northern Ireland’s HM Maze

When the mass escape from Northern Ireland’s HM Maze Jail occurred in 1983, it was the largest in British history, with one prison guard dying of a fatal heart attack and 20 others being injured.

The escapees were a group of 38 IRA members who had been convicted of crimes like murder and arson. They had guns smuggled in, which were used to hold the guard’s hostage. Upon the arrival of a food supply truck, the convicts took the driver hostage and forced him to take them out.

Nineteen of them were caught and imprisoned again during the next three days. As for the others, some escaped to the United States, but were eventually apprehended and extradited, while others were given amnesties.

The Texas Seven

Seven inmates at the maximum-security John Connally Unit in Karnes County, Texas, busted out of the facility in 1999 through a combination of brute force and campy deception.

The ragtag group, led by a prisoner called George Rivas, lured a warehouse maintenance supervisor inside and knocked him out with an axe handle to the head. This started a chain of events that forced them to use the same strategy to get two prison guards and seven other maintenance men out of the way, as well. The inmates stole staff clothes, firearms from one of the prison’s watchtowers, and the keys to a prison vehicle to escape.

The Texas Seven went on a crime rampage throughout Texas before being apprehended in Colorado shortly afterward.

John Dillinger

As America’s public enemy number one in the early 1930s, John Dillinger was on the run after a string of bank and police station robberies. He was responsible for the deaths of ten people.

When Dillinger was ultimately apprehended in January 1934 in Tuscon, Arizona, the authorities put him in a secure prison. But the prison only held onto him for two months. Dillinger is believed to have made a fake pistol out of wood and darkened it with shoe polish with the help of another convict. He forced his way out of the jail, brandishing this phony weapon, and fled in the sheriff’s brand-new V-8 Ford.

Dillinger was gunned down in Chicago by FBI operatives later that year.

Jay Junior Sigler

In 1998, Jay Junior Sigler was freed by a massive truck driven by his buddy John Beaston, which managed to barge through four security barriers at Everglades Correctional Institution.

The large truck was trailed by another vehicle driven by the inmate’s mother, Sandra, into which the three loaded together with accomplices Christopher Michelson and Kelly Mitchell. After leaving the prison, the group changed cars and split up. Jay and Michelson were caught after they hit another car and killed its driver while police were pursuing them.

Sandra, who was believed to have orchestrated the escape at the time, was apprehended shortly after the car swap at a gas station a few miles from the jail.

Frank Abagnale Jr.

Anyone who has watched the Leonardo Di Caprio film “Catch Me If You Can” knows that Frank Abagnale was an expert impersonator of pilots, physicians, and attorneys. Many don’t know that he impersonated a prison inspector.

When Abagnale was arrested in 1971, he managed to flee the Federal Detention Center in Atlanta, Georgia. With the assistance of an outside collaborator, he convinced the guards that he was an undercover inspector at the jail.

It helped that a US Marshal forgot to bring Abagnale’s detention papers when he brought him to the facility. After a few weeks of building a watertight alibi, the conman walked out of the facility without being challenged.

The correctional officers who Abagnale had tricked never saw him again, and he was able to enjoy two months of freedom until being apprehended in Washington and sent to a jail in Virginia.

The ex-convict now assists the FBI on white-collar investigations.

Robert Dale Shepard

Dental floss can improve your dental hygiene, but felon Robert Dale Shepard discovered another use for it while imprisoned in West Virginia in 1995.

Shepard braided seven reels of the cavity-fighting thread together and fashioned it into an 18-foot rope ladder. When he connected the homemade ladder to a cinder block and threw it over the jail wall, it was as strong as telephone wire and was able to support his weight without breaking. He was on the run for 41 days until the police apprehended him and returned him to prison.

In the wake of the incident, many jails prohibited dental floss.

Escape from Alcatraz

Even the FBI stated that Frank Lee Morris and John and Clarence Anglin’s 1962 escape from the historic Alcatraz prison was remarkable. To be fair, it was brilliant. The three inmates began by making false heads out of soap, toilet paper, and real hair and placing them under their bedsheets to fool the guards into thinking they were asleep.

They dug tunnels in the adjacent cell walls and burrowed their way to an empty service corridor, gaining access to the jail roof through a ventilation shaft. After making it to the shore, they built a raft out of raincoats and contact cement and fled the island. Nobody realized the trio had gotten away until the following day.

After no sign of them was found on the neighboring Angel Island or during the 17-year FBI investigation that followed, it was assumed they drowned in the water.

The conspiracists, on the other hand, will tell you differently.

Antonio Ferrara

Explosives were always Antonio Ferrara’s specialty. The bank robber’s signature move was to blast the hinges off safes and vaults without destroying the money inside.

When the authorities caught up with him, he was condemned to eight years in France’s Fresnes Prison. But that didn’t last long, and his escape was dramatic. Ferrara blasted his cell door off using explosives that were alleged to have been handed to him by a guard working for him.

A group of accomplices then rushed the joint with rocket-propelled grenade launchers and AK-47s, assisting the felon in fleeing the main penitentiary. After a large-scale undercover operation, Ferrara was apprehended at a Paris club four months later.

Pascal Payet

When the French authorities sentenced Pascal Payet for the murder of a truck driver, they made the mistake of sending him to Luynes jail, which was easily accessible from above. Thus, when several of his associates hijacked a chopper, they were able to hightail it over there and haul him up with relative ease.

The operation worked so well that Payet returned two years later by helicopter to pick up several of his friends, but he was apprehended and sent back to prison.

Due to his penchant for flying away, the criminal became one of the most guarded inmates in French prison history and was often transported from jail to jail without notice, making it impossible for his accomplices to ascertain his whereabouts. But it didn’t stop him from fleeing by helicopter once more, this time on Bastille Day in 2007.

He’s now back in prison, with additional years added to his sentence as retribution for his helicopter escapades.



Leave a Reply

Your email address will not be published.