5 Most Creative Prison Breaks

Lawyer Hugo Grotius

5Lawyer Hugo Grotius


In the sixteen hundreds Dutch Arthur Hugo Grotius found himself at the mercy of the courts when his writings about natural law and justice butted heads with the established religious beliefs of the country.

After being imprisoned and analyzing the movements of the guards, when they weren’t looking Grotius hit away in a three-and-a-half-foot book chest and was subsequently moved out of the prison and onto a ship after a few close calls by the guards. Grotius found himself transported to a city in the Netherlands where he made his final escape.

Carpenter Jack Shepherd

4Carpenter Jack Shepherd


Jack Shepherd made breaking out of prisons his specialty. A carpenter's apprentice who had taken to crime to pay for his lavish lifestyle was seized by the authorities and imprisoned a number of times in London… only to make daring escapes every time! His means of escape changing every time, Sheppard broke through ceilings, utilized bed sheets as ropes and even cross dressed his way to freedom.

Making fools of the guards, he made a name for himself as a local hero. Sheppard's final escape included maneuvering his way out of a pair of handcuffs, barreling through six barred doors and busting through the prison ceiling to freedom. No prison was sturdy enough to keep Sheppard from escaping which is why upon his next capture he was quickly hung in public.

Bank Robber John Dillinger

3Bank Robber John Dillinger


Famed bank robber John Dillinger was as crafty as he was dangerous. After his first prison escape in which a group of gang members freed him by murdering the guards, Dillinger found himself in a new cell with a potato, shoe polish, a razor and a will to break free. He carved the potato into the shape of a handgun, painted it black with the shoe polish and finally managed to escape using the fake gun.

As a threat to nearby prison guards, he disappeared soon after that for a number of weeks. His frivolous lifestyle eventually became his downfall after the FBI caught wind of Dillinger's whereabouts in the outside world. He was killed in a shootout outside a movie theater.

The Alcatraz Three

2The Alcatraz Three


The famed Alcatraz prison has been home to many daring escapes, but few if any survivors passed the rough ocean waters. However, that didn't stop three prisoners in 1962 whose plans included digging into ventilation ducts with stolen cafeteria spoons and creating paper Mache heads to sit in their beds and hide their disappearances from guards.

After they reached the roof of the prison and crossed the heavily fenced coast they got aboard a make shift raft made of raincoats and cement adhesive and sailed away into the sea they were never heard from again.

Drug Lord Joaquin Guzman

1Drug Lord Joaquin Guzman


Mexican drug lord Joaquin Guzman's aka El Chapo laughed in the face of prison constructs. Rich from his drug trafficking empire, Chavez’s first days in prison ended after he reportedly paid off guards and police to aid his escape. He subsequently hid in the Mexican mountains for thirteen years after breaking free but then found himself in custody once again.

His next prison visit ended with a tunnel dug under his shower leading to another mile-long tunnel almost six feet tall where he drove a motorcycle to a nearby construction site and his freedom. Chapo recently was the feature of a number of media headlines, after he professed to the public his hatred of American businessman and Republican candidate for president Donald Trump. He was recaptured in January after inviting Hollywood producers to his home to make a movie about his escapes.