The Most Insane Prison Escapes in History

Some of these men escaped prison by mailing themselves out, losing 25 pounds to slip through bards, digging long tunnels, driving a prison truck through the prison gates or simply flying off in a helicopter. They did it against all odds, and their prison escapes stories are mesmerizing, mind blowing, almost unbelievable.

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7 Insane Prison Escapes You Won’t Believe Happened

Some had help on the outside, others planned it all on their own for months or years. Let’s hear their prison escapes stories and ponder at the lengths to which people will go for a taste of liberty.

1. This man mailed himself out of prison

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On April 5th, 2006, an inmate named Richard McNair managed to escape from the United States Penitentiary in Pollock, Louisiana by literally mailing himself out to freedom.

His usual prison yard work involved fixing up old mailbags. During his work hours, he crafted an escape pod complete with a breathing tube and hid himself beneath a pile of mailbags. The mail bags were moved on a pallet to a warehouse outside the prison’s perimeter, and the prison staff left for lunch. That’s when McNair cut through the shrink wrap and his makeshift pod and walked away unfettered.

Things become even crazier when, just hours after his escape, he was stopped by a police officer who saw him running along a railroad track. Their encounter was captured on the patrol car video cameras. Despite McNair giving the police officer two different names, he managed to convince the officer that he was just out for a run and was in town to lend a hand with some repairs after Hurricane Katrina.

Richard McNair was the first person to break out from a federal prison since 1991 and that landed him on the US Marshals 15 Most Wanted List. Despite the widespread media coverage, McNair was able to reach Canada and stay off the radar for almost a year. He was caught again in October 2007, and he’s now serving his time at the United States Penitentiary, McCreary in Kentucky, which is a high-security federal prison.

2. This man escaped prison by helicopter – insane prison escapes

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You know, prisons are notorious for having big walls, fences and barbed wire everywhere. So, why not just fly over them to escape?

That’s what Redoine Faid, one of France’s most notorious criminals, thought, too. At around 11:30 am on July 1, 2018, he sensationally escaped from a prison in Reau in a helicopter.

His accomplices had hijacked the helicopter from a nearby airfield, having posed as flight school students. Under threat, the flight instructor hovered in the prison’s main courtyard, while the men cut through a prison door and burst into the visiting room where Faid was talking to his brother.

After everyone was on board the helicopter, they took off. The authorities later discovered the helicopter near Charles de Gaulle Airport, leading them to believe the men switched to a car to make their getaway. The flight instructor was found unharmed.

Isn’t this one of the most insane prison escapes ever? Wait until you hear the next one.

3. This man escaped by losing 25 pounds  – insane prison escapes

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Ted Bundy is one of the most notorious serial killers in American history. He admitted to killing 30 people, and he was eventually executed in the electric chair in January 1989.

He tried to escape custody and prison several times. First time, in 1977, while Bundy was at a courthouse in Aspen, Colorado, acting as his attorney, he requested to use the law library for research during the court recess. When the guard stepped out for a smoke, Bundy jumped out of the second-story window. Despite injuring his ankle in the fall, he managed to flee in the nearby mountains, where he found refuge in a cabin for a few days before stealing a car.

However, a deputy pulled him over after spotting the car weaving along the road, and 6 days after his escape, Ted Bundy was again behind bars.

Bundy’s second escape was even more audacious. After his transfer to the Garfield County Jail in Glenwood Springs, Colorado, he found himself in a cell with a loosely secured grate and a light fixture that was scheduled for welding but remained unfixed. He realized that he could fit through that opening in his cell’s ceiling if he was thinner. So he lost between 20 and 25 pounds, and one night he finally squeezed through, navigated through the jail’s ductwork and descended into an unoccupied jailer’s apartment. He found civilian clothes, changed and vanished into the night on December 30, 1977.

Unfortunately, he made 2 more victims until he was caught again and sentenced to death.

4. These 7 men escaped prison in a prison pickup truck

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On December 13, 2000, seven inmates orchestrated one of the most complex prison escapes in American history.

They managed to overpower and secure 9 civilian maintenance supervisors, four correctional officers and three inmates who were not involved in their plan.

It all started during the prison’s lunch time, which was the “slowest” moment in prison, with the most reduced surveillance, especially in the maintenance department.

They distracted and knocked out several maintenance workers, bound and gagged them, after stealing their clothes, credit cards and IDs. Impersonating the civilian maintenance workers, 3 members of the group approached the prison’s back gate under the pretense of installing video monitors. They overpowered the guard there, seized control of the guard tower and stole multiple weapons. Meanwhile, the other four who stayed behind, called the prison tower guards to distract them. Then they stole a prison maintenance pick-up truck, which they drove to the back gate of the prison, picked up the others and drove away right through the prison gates. They even left a note that read: “You haven’t heard the last of us yet”.

During their time on the run, they robbed a Radio Shack and a sporting goods store where they shot and killed a police officer. Six of them were eventually caught by the police. The seventh chose to end his own life rather than face capture again.

5. These 2 men escaped using love as their weapon

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(L-R) David Sweat and Richard Matt are shown undated photos released by the New York State Police.

Richard Matt and David Sweat, both serving sentences for murder, managed a daring escape from the Clinton Correctional Facility in Dannemora, New York. They climbed through holes they had cut in the cell walls. They squeezed through tunnels and between walls and through a steam pipe, which took them underneath the prison. From there, they popped out of a manhole in the village. It was pure Shawshank shebang.

But how did love help them? Well, they were helped by Joyce Mitchell, a prison corrections officer, who had developed a romantic attachment to both men. She allegedly engaged in multiple sexual encounters with the men in the tailor shop she supervised.

Mitchel helped the men by smuggling in chisels, hacksaw blades and other tools the men used to cut and  dig through the prison walls. They were hidden within frozen hamburger meat, and delivered to Matt and Sweat.

The men were caught a few weeks after their daring escape, however. Matt was fatally shot by the police, while Sweat was captured just two days after.

6. This man escaped prison on a motorcycle  – insane prison escapes

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Yuri Cortez / AFP/Getty Images

Picture this – It’s the steamy summer of 2015, and Joaquín “El Chapo” Guzmán, the boss of the Sinaloa cartel, is chilling (well, sort of) in El Altiplano, a maximum-security prison near the city of Toluca, waiting on making his most daring prison escape ever. Less than a year earlier, in February 2014, after a 13-year-long game of hide-and-seek, the authorities finally managed to get their hands on him. But the moment he entered his prison cell, El Chapo was already planning his escape. The plan? To dig a mile-long tunnel from a shack outside the prison right to the shower inside his cell. Yeah, you heard that right.

It turns out, Emma Coronel, El Chapo’s wife, was one of the masterminds of the escape, coordinating the whole operation with their sons.

They bought land near the prison, and started digging. They even managed to sneak a smart watch into El Chapo’s cell to pinpoint his GPS location for the tunnel.

Plan complete. Time to go

By July, everything was set. El Chapo planned his great escape on a lazy weekend, when security was slower. CCTV cameras caught his last act in the cell – a casual stroll behind a wall for a shower that ended with a poof! He vanished.

El Chapo made his grand exit on a motorcycle fitted on rails, through a tunnel that had more amenities than some apartments—lights, air, you name it. At the tunnel’s end, an ATV awaited, ready to zip him to a prepped warehouse. From there, a flight on a trusty pilot’s wings carried El Chapo to his Sinaloa mountain retreat.

But freedom was short-lived. By January 2016, after a showdown in Los Mochis, El Chapo was back in his less-than-luxurious state accommodation, plotting yet another escape that would require a $2 Million bribe. But before they could put the plan into action, El Chapo was transferred to another prison, where he was held until his extradition to the United States in January 2017.

7. The 1962 escape from “The Rock”

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More than 60 years ago, on the night of June 11, 1962, 3 inmates – Frank Lee Morris, and the brothers Clarence and John Anglin were locked down as usual in their cells on a maximum security prison situated on an island in San Francisco Bay.

Guards walked outside their cells and checked on them periodically all night, and yet, come morning, the inmates had vanished. Under the bedclothes, there were only pillows and lifelike papier-mache heads with real hair and closed painted eyes. A massive manhunt began, but all they found was a crude raft made of rubber raincoats.

So, how did these 3 escape the infamous Alcatraz?

They used spoons from the mess hall and a drill improvised from a vacuum cleaner to dig through concrete walls and reach a narrow, rarely-used utility corridor for heating ducts and pipes that happened to be just behind their row of cells.

They timed the absences of the guard patrols, and managed to create a secret workshop atop their cell block where they improvised an inflatable raft of rubber raincoats bound together with thread and contact cement.

So, on the night they escaped, they made their way to the roof. Right under the watchtower’s nose, they made a daring 50-foot descent down a kitchen vent pipe to the ground. Searchlights might have been sweeping over the walls, but somehow no one spotted them. Maybe the guards couldn’t believe someone would actually dare escape that way.

Once on the ground, the 3 men climbed a 12-foot high fence topped with barbed wire and made their way to the northeast shore, which was perfectly hidden from the searchlights and gun towers. This is where they got their raft ready, pumping it with a hand-held accordion, and disappeared into the foggy waters.

The next morning, the search team found bits of their raft and paddles on Angel Island, not too far from Alcatraz. They also found a plastic bag with personal items belonging to one of the escapees. Not being able to find them, the officials assumed that the prisoners had drowned in the turbulent waters of the San Francisco Bay.

Eventually, in 1963, almost one year after the famed escape, Alcatraz was closed for good and later became a tourist attraction.