Top 15 Most Insane Prison Escapes Ever

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Being in a prison cell sure does crazy things to prisoners, like planning extravagant escape routes. Statistics show more than 2000 Americans plot an escape route annually!

Although very few actually win their way to freedom. From riding helicopters to digging holes these prisoners have done it all! Here are the top 15 most insane prison escapes ever.

Top 15 Most Insane Prison Escapes Ever

1. The Madhya Pradesh Escape

On October 2013, Seven inmates escaped from a prison in the central Indian state of Madhya Pradesh, police say. A 5.4m (18ft) escape route was found in a part of Sabarmati jail that houses prisoners on trial for bombings. The route was formed by digging through toilets. It is believed that the prisoners crawled their way out to freedom.

2. Ted Bundy escapes

The cell from which Bundy made his escape

Bundy carved an opening in the ceiling of the cell. On the day of the escape, he arranged some pillows and books on his bed and covered it with a blanket so it appeared as though there was a body in the bed. He then crawled through the duct that he carved earlier and escaped free.

3. John Dillinger

John’s carved wooden gun

John Dillinger was a genius with artistic talent. He managed to escape point jail America by threatening the guards in charge with a wooden gun. He meticulously carved out a wooden fake gun from a piece of wood. He then stole the sheriff’s car and drove away to freedom.

4. The opportunity escape

A man handcuffed to a plastic chair in a Mumbai police station in 2015, simply “kept the the chair on his head” and “walked off” rather casually when the watching policeman left the room to run an errand.

5. Richard and David escape


Two American prisoners pulled off an elaborate prison escape after using power tools to cut through the steel walls of their cells.

Richard Matt, 48, and David Sweat, 34 apparently crawled along tunnels to flee the all-male Clinton Correctional Facility in Dannemora. The two men, who were both serving time for murder, left the guards a note that read “Have a nice day”.

6. Escape from Alcatraz

The Alcatraz prison

Clarence Anglin, John Anglin and Frank Morris were serving time for a litany of crimes including bank robbery and car theft when they resolved to flee Alcatraz and its claustrophobic confines.

The trio cut holes in their cell walls, leaving behind dummy bodies in their beds to fool guards into thinking they were still incarcerated.

7. Korean Houdini

Yoga practitioner Choi Gap-bok provided the history books with a new take on prison escape methods. Rather than bend his cell bars out of shape, he bent himself out of shape, slipping through the tiny slot at the bottom of the cell that’s used to give prisoners food. The manoeuvre apparently took only 34 seconds.

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8. The flying criminal

Pascal 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, he orchestrated a rerun of the events to help three more prisoners escape the confines of the jail.

9. El Chapo

Pictured alongside Chapo, the laundry baskets.

In 2001, drug kingpin El Chapo escaped from prison in a dirty laundry basket after he bribed multiple guards to wheel him out of prison in it. He spent 2.5 million dollars in bribing 70 guards, one of whom is in prison for it.

10. El Chapo escapes again

El Chapo was arrested again and kept at Altiplano Federal Penitentiary. He stayed there for less than 17 months and escaped by getting a custom labyrinth built underneath his cell. The bribes and the escape route for this escape cost him over 50 million dollars!

11. The spoon escape

Three men from the Alcatraz prison used some spoons to dig tunnels in their cells that led to an unguarded utility corridor. Then they climbed up the roof, down a 50-inch drain pipe, over a 12-foot security fence, and then inflated a makeshift raft to use in the sea below. Their bodies were never found.

12. Nazis escape

In 1942, Kazimierz Piechowski, an Auschwitz prisoner, escaped the camp along with three others by dressing up as Nazi officers and stealing a German captain’s car. When they arrived at the gate he simply shouted orders to the guards who let them pass with no questions asked.

13. Yoshie Shiratori

Yoshie Shiratori, the “Showa Era escape artist,” is known for having escaped from prison four times by picking locks with wire, sawing floorboards with metal sheet, and digging his way out with a bowl.

14. Daniel Heiss

In 1995, Daniel Luther Heiss escaped prison after discovering that the key pictured on his prisoners’ information handbook was the master key for the entire prison, which he replicated and successfully unlocked his prison cell.

15. Hacksaws and hamburgers

killers David Sweat and Richard Matt in order to escape, 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.

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