On this list, you’ll find the craziest, most outlandish, and outright insane real-life prison escapes in history — from a Japanese escape artist who couldn’t be held to the most inventive inmates on Alcatraz Island. Though every prison is constructed for the sole purpose of keeping criminals behind bars, these famous prison breaks prove no facility can contain human ingenuity.
Prison escapes date back as far as the institution of prisons itself. Humans don’t like to be confined, and when convicts have nothing left to lose, they’ll take the risks involved with a shot at tasting freedom. Some imaginative souls have even gone beyond what prison architects were capable of accounting for…
1) Craziest British Prison Escapes: The Tower of London’s First Inmate
This famous prison escape goes way back. The Tower of London, built in 1070, quickly earned a reputation as one of England’s most notorious prisons. Even so, it didn’t take long for the Tower’s inmates to start plotting prison breaks. The first known escapee was also the Tower’s first prisoner: Bishop of Durham Ranulf Flambard.
Flambard spent six months behind stone walls before hatching a plan to break free, as The Northern Echo explains. On February 2, 1011, he requested a very special barrel of wine — one concealing a hidden rope inside.
The bishop served the guards drink after drink until the booze overtook them and they passed out. He then retrieved the rope from the cask and lowered himself down the prison walls. Flambard’s friends waited below with horses in hand. Speed was the name of the game if they wanted to get Flambard to safety.
The Bishop of Durham outran the tower’s guards, eventually reaching a ship bound for Normandy. With the wind behind the sails, he successfully evaded recapture.
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2) Escape From Libby Prison: One of The Largest Prison Breaks in History
In 1864, one of the largest prison escapes in history took place at Libby Prison in Richmond, Virginia. Two imprisoned soldiers — Union Colonel Thomas E. Rose and Major A. G. Hamilton — led the charge.
The officers assembled a group of 13 men, and with their help, they dug a tunnel out from the prison’s lower level. Guards avoided this floor, which they dubbed “Rat Hell,” due to the area’s severe river rat infestation. Without oversight, this was the perfect place to work. And despite terrible conditions and a tunnel collapse that killed two of their men, the escapees pressed on.
On the night of February 9, 1864, 109 Union soldiers used the tunnel to escape Libby Prison. However, not everyone made it to freedom. According to Living Through Rat Hell: The Lives and Escape Attempts of Soldiers at Libby Prison, a total of 48 soldiers were recaptured and thrown into Rat Hell. Two others drowned during the escape. The rest vanished into the night, away from the clutches of the Confederate Army.
3) Most Inventive Japanese Prison Escapes: Japan’s Harry Houdini Escaped Prison Four Times
In Asia, Yoshie Shiratori earned the title “man no prison could hold” by designing four of the most inventive prison escapes in the 1930s and ‘40s. Shiratori was after more than freedom, however. His goal was to break free of the inhumane treatment he suffered in Japan’s prison system.
According to an article by Tokyo Weekender, Shiratori made his first escape by picking a cell lock with the metal wire off his bathing bucket. He then climbed through a cracked skylight. Unfortunately, authorities soon recaptured Shiratori and sent him to an even harsher facility.
At the new prison, the convict remained handcuffed at all times. This still couldn’t stop Shiratori, who slipped his restraints one night and escaped through another skylight.
Again, Shiratori’s freedom was short-lived. Police caught him after only three months. Japan’s Houdini made the mistake of visiting one of his former guards to ask for advice on changing the country’s prison system.
Back in custody, he utilized miso soup for his next escape. He spat on the bolts of his shackles, using the salt to corrode the metal until it broke. Then, he dislocated his shoulder so he could climb through the food slot in his cell door. This escape bought him two years in the wild.
Two years later, Shiratori killed a man over stolen tomatoes. Authorities arrested him once again. Shiratori claimed self-defense in the manslaughter, but the court didn’t buy it. So they sentenced him to death.
In his cell at Sapporo Prison, guards watched him around the clock. Even with all eyes on him, Shiratori dug beneath the floorboards with nothing but a miso soup bowl, marking his fourth and final escape.
4) The Greatest Prison Break: An Escape from Alcatraz Island
This Alcatraz mystery is one of history’s most famous prison escapes. In June 1962, Frank Morris and brothers John and Clarence Anglin seemingly disappeared into thin air. Over six months, the crew of inmates painstakingly widened ventilation ducts in their cells using makeshift tools.
According to the FBI, the trio made a drill out of a vacuum cleaner motor to grind away at the structure. Then, they used cardboard boxes to conceal their workspace, while music muffled the noise of tools scraping away concrete. To combat the roaring sea, the inmates crafted life vests and a raft from over 50 raincoats, sealing them with heat from steam pipes.
On the night of June 11, the escapees placed dummy heads in their beds to fool guards before navigating their way through the vents and onto the roof. Once out, they launched their raft into San Francisco Bay’s icy waters.
The authorities still haven’t found conclusive evidence of Morris and the Anglin brothers’ fate. The FBI closed the investigation in 1979, concluding the men had drowned. However, the U.S. Marshals Service keeps the case open in case new evidence ever surfaces.
5) A Serial Killer’s Double Prison Escape: Ted Bundy Breaks Out Twice
In 1977, one of the most infamous serial killers ever, Ted Bundy, managed not one, but two prison breaks. The first incident, according to Rocky Mountain News, occurred at the Aspen, Colorado, courthouse while he awaited trial.
Bundy acted as his own attorney during his trial for the murder of Caryn Campbell. Representing himself entitled Bundy to the use of the courthouse library to research legal information relevant to his case.
The killer waited until he was alone in the library, then jumped from a second-story window and ran. He was only on the run for six days before officers found him behind the wheel of a stolen car. Of course, Bundy still had some tricks up his sleeve.
Later that year, he escaped again. This time, Bundy climbed into a jail crawl space he’d accessed by sawing through the ceiling. He then dropped into a jailer’s empty apartment, changed into civilian clothes, and walked right out the front door. The guards didn’t notice the serial killer was missing for 17 hours.
Bundy then went to Florida and unleashed a wave of violence. During the run, he made it onto the FBI’s Ten Most Wanted Fugitives list and he took the lives of three more women. On February 15, 1978, police recaptured Bundy for driving yet another stolen car.
6) Daring Prison Breaks: A Cult Leader’s Chopper Getaway
In 2009, convicted cult leader and child abuser Juliano Verbard pulled off one of the most shocking prison escapes in France, and he did it by helicopter. Though the use of aerial vehicles in a prison break might seem unique, France 24 says it marked the country’s 11th helicopter escape since 1986.
Verbard led the cult called Sorrowful and Immaculate Heart of Mary, claiming he received monthly visions of the Virgin Mary. He built a devout following and profited from membership dues. In 2008, a court sentenced him to 15 years for sexual crimes against children. After sentencing, the courts sent Verbard and two of his followers to Domenjod Prison on Reunion Island.
While in Domenjod, two of Verbard’s cohorts posed as tourists and boarded a helicopter. Then, they hijacked the aircraft at gunpoint and forced them to land in the prison yard so Verbard could hop in.
The helicopter flew the gang to a nearby field, where they had planted a getaway van. From there, Verbard and his men vanished, leaving the pilots unharmed.
Many mainland prisons in France have installed nets above their prison yards to cut down on the number of helicopter-based prison escapes.
7) A Mile-Long Getaway: El Chapo’s Tunnel to Freedom
In July 2015, drug lord Joaquín “El Chapo” Guzmán managed to escape from a supermax prison in Mexico. The Sinaloa Cartel mastermind vanished through an intricate mile-long tunnel the cartel had dug under the facility. As TIME explains, the tunnel was equipped with lighting, ventilation, and a motorcycle mounted on rails.
The escape was a major embarrassment for Mexican officials. It also put El Chapo at the center of an internationally broadcast global manhunt. According to the BBC, Guzmán outwitted law enforcement for six months before authorities recaptured him on January 8, 2016, following a shootout with Mexican Marines.
This wasn’t Guzmán’s only prison escape either. The U.S. Department of State says the cartel leader executed his first prison break in 2001 and retained his freedom until 2014.
In 2017, Mexico extradited him to the U.S. By 2019, the U.S. courts sentenced him to life behind bars, but only time will tell if El Chapo will stay there.
8) Clinton Correctional Facility: A Real-Life Shawshank Prison Escape
The Clinton Correctional Facility escape took place in 2015. On June 6, guards discovered that Richard Matt and David Sweat were missing during a routine bed check.
The convicts spent the nights leading up to their escape cutting through a steam pipe large enough for them to wiggle through. They even took the time to outfit the pipe with lights and ventilation. All it took was manipulating prison staff into smuggling them frozen hamburger meat containing tools.
They left their cells at approximately 11:00 p.m., crawled through the pipe, and exited a manhole around 11:50 pm, as the Inspector General at the time explained. Seven hours passed before guards noticed they were missing.
After three weeks on the run, a U.S. Border Protection tactical team fatally shot Matt. Two days later, according to Fox2, officers shot and captured Sweat two miles from the Canadian border.
9) Heartfelt Prison Escapes: A Breakout in Alabama
On April 29, 2022, Assistant Director of Corrections Vicky White assisted convict Casey White in executing what some may call one of the most heartfelt prison escapes to date. According to CNN, Vicky reportedly fell in love with the murder suspect and granted him special privileges at Northwestern Alabama’s Lauderdale County Jail — including a way out.
On the morning of the escape, Vicky handcuffed Casey and shackled him in her patrol car. She lied and told other officers he was attending a health screening. In truth, Vicky would abandon her vehicle in a shopping center parking lot a mile from the facility, and join Casey on the run. The two evaded authorities by frequently switching getaway cars.
Their days of freedom, however, would come to an end on May 9.
Officers spotted the couple in a vehicle and attempted to pull them over. Vicky sped away but was rammed by police cruisers, causing her to crash into a ditch. Instead of being captured, Vicky shot herself in the head.
Casey surrendered and was taken back into custody. His consecutive sentences will leave him spending the rest of his life behind bars.
10) Acrobatic Prison Breaks: Danelo Cavalcante’s Escape
Danelo Cavalcante was the subject of one of the most-watched manhunts in recent history. On August 31, 2023, he pulled one of the most acrobatic prison escapes ever from Chester County Prison while awaiting transfer to a state facility. A judge had recently sentenced him to life for murdering Deborah Brandão, a former girlfriend.
Surveillance footage captured Cavalcante’s parkour-style escape. The inmate crab-walked up between two walls, scaled a fence topped with razor wire, and jumped onto the roof before disappearing into the woods. He and his stunt quickly went viral.
While on the run, Cavalcante stole food, clothes, and a truck. Residents nearby lived in fear, locking their doors and keeping watch for the perp. One civilian even spotted him in a garage trying to steal a rifle.
Two days later, planes using thermal imaging located Cavalcante. It was a K-9, though, that ultimately sniffed him out. This ended the 14-day chase and added 20 new charges to Cavalcante’s rap sheet.
