11 daring prison escapes, and how they did it

11 daring prison escapes, and how they did it

Escape scenes in movies are always a favourite of mine. Whether they are tense, scary, or thrilling, there's a sense of excitement which comes from these sequences that is palpable. So, I have always wondered if there were any real prison escapes attempts where an inmate actually pulled it off, just like you see in the movies.

I wrongfully assumed that real history would be far less interesting than fiction, as I came across numerous jail-breakers, some of which used the most ingenious schemes to fly the coop.

1. Giacomo Casanova

During his exercise walks inside the prison garret, the Italian adventurer found a piece of marble and an iron bar. He smuggled them back to his room, sharpened the bar into a spike using the marble. Collaborating with the prisoner in the next cell, he smuggled the sharpened pole to his neighbour inside a bible. The prisoner made a hole in his ceiling, climbed across and made one in Casanova's roof.

The pair escaped onto the roof of the Palace and entered another window. With his bed sheets, they lowered themselves into a room 25 feet below. They stole clothes, and broke a lock to pass into a palace corridor. Convincing a guard they had inadvertently been locked into the palace after a function, they walked right out the front door.

Casanova prison escape Credit: Google Books

2. Jack Sheppard

Jack Sheppard may have just been a petty burglar, but he became infamous for his admirable four successful escape attempts, the most notable of which were the third and fourth. While awaiting his execution, Sheppard's visitors distracted the guards as he removed an iron spike from a vent he had loosened earlier. His slim build helped him slip through, and escaped the building using women's clothing his visitors had smuggled in.

In his final escape, Sheppard managed to slip his handcuffs off and remove his chains with a crooked nail before breaking through the ceiling using an iron bar he removed from the chimney. From the roof he crossed onto the roof of an adjacent house. Sheppard convinced a passing man to help him remove his manacles after telling him that he had been wrongly imprisoned.

The fifth arrest lead to him being observed at all times and loaded with 300 lbs of iron weights. He planned one more escape, where he would cut the ropes binding him on the way to his execution, but it was foiled when the pen-knife was found by a guard shortly before he left for the gallows.

Jack Sheppard escape Credit: Executedtoday.com

3. John Dillinger

"I know he's a bad baby and a jailbreaker but I can handle him," Sheriff Lillian Holley said of John Dillinger, but he would soon have to eat those words. The infamous gangster and bank robber had already been broken out of jail once, so it was an even bigger surprise when he did it a second time.

Dillinger was taken to the jail in Crown Point, Indiana, after being wanted by the authorities for killing a policeman. The police bragged that the prison was escape-proof to the media to satisfy concerns, but they were proven wrong when Dillinger broke out of prison by holding one of the guards by gunpoint, locking them in his cell before fleeing the scene in the sheriff's own car.

The twist is, Dillinger claims that he didn't have a real gun, but instead made a fake one from whittling down wood, then covering it in shoe polish. "If I ever see John Dillinger," Sheriff Holley said when he was asked about the events, "I'll shoot him dead with my own pistol. This is too ridiculous to talk about."

John Dillinger newspaper Credit: The Paul Rosa Collection

4. Yoshie Shiratori

Yoshie Shiratori escaped from prison four times, and was sentenced to life imprisonment after his first recapture. He escaped again in 1942, through an air vent in the prison's ceiling. For his third escape he used an unusual method - rusting his handcuffs and the lock on the cell door by applying miso soup to the metal over time. Once they were weak enough, he broke them and escaped.

He was arrested in 1946, and escaped again in 1947. This time he sawed through the floorboards of his cell with a sharpened piece of sheet metal, then dug through the earth beneath with a bowl. In 1948, after being given a cigarette from a friendly police officer, he admitted to being an escaped convict. He remained in prison until he was released in 1961, before passing away in 1979. A memorial to Shiratori is located inside the Abashiri Prison Museum.

Yoshie Shiratori memorial Credit: Ikidane Nippon

5. André Devigny

In 1940, André Devigny became part of the anti-Nazi resistance movement during the German occupation of France. As well as feeding information to British Special Operations, Devigny helped fleeing refugees and sabotaged German military supplies. In 1943 the Gestapo infiltrated his group and arrested him, sending him to Montluc Prison.

Devigny was tortured for information and violently punished for his many escape attempts, eventually being sentenced to death. A week before his execution, he removed his handcuffs with a safety pin, ground the end of a spoon to a point on the concrete floor of his cell, using it to pry off the wooden slats at the bottom of the cell door, leaving him enough room to squeeze through.

Using a rope made from bedsheets and a grappling hook made from the frame of a broken lantern, he escaped through a skylight. He killed a sentry with his own bayonet and sneaked past another. He climbed one wall and threw the grappling hook across a 15-foot gap to the outer wall, escaping to the streets on the other side. Eluding search parties, he fled to help with the resistance forces in Switzerland.

Andre Devigny Credit: MUBI

6. The 1962 Alcatraz escape

The Alcatraz Federal Penitentiary suffered a number of failed escape attempts by its inmates. But one attempt is thought to have been successful: that of Frank Morris, John and Clarence Anglin.

The inmates worked at night over 6 months, using discarded saw blades, stolen spoons, and a drill made from the motor of a vacuum cleaner to widen ventilation ducts in their cells. The noise was covered by Morris playing his accordion and the holes were covered with cardboard and paint. From here they climbed on top of the cell block and set up a workshop. They turned 50 raincoats into life preservers and a rubber raft, stitched together and heat-sealed with steam from pipes, and built paddles from scrap wood.

They made their escape through the roof, concealing their disappearances using dummy heads made from the papier-mâché-like mixture of soap and toilet paper, paint from the maintenance shop and hair from the barbershop floor. They descended 50 feet by sliding down a vent pipe, then climbed over two barbed wire fences to a blind spot in the prison's searchlights, where they inflated their raft.

After a search turned up nothing but remnants of the raft, the FBI ruled that the strong currents likely lead to their drowning. However, in 2012, the Anglins' family made public their belief that the brothers were alive. Another sibling had told family members on his deathbed that he had been in contact with the brothers from 1963 until 1987.

Frank Morris fake head Credit: FBI.gov

7. The Mountjoy Prison Helicopter Escape

IRA members Seamus Twomey, J.B. O'Hagan and Kevin Mallon escaped from Mountjoy Prison in 1973. They escaped by climbing aboard a helicopter that landed in the prison exercise yard, which was hired from Dublin airport for an aerial photo shoot. The pilot was asked to pick up the equipment on the way, at which point two masked men emerged and hijacked the vehicle.

He was forced at gunpoint to fly to the prison without registering his flight path with air traffic control, landing in the exercise yard. Fights broke out between the guards and prisoners as they realised an escape attempt was taking place, and as the guards were distracted the trio boarded the helicopter.

They were taken to an unused racecourse, where the escapees were transferred to safe houses via a hijacked taxi. Mallon was captured in December that year, O'Hagan was captured in 1975, while Twomey managed to evade recapture until 1977.

Helicopter escape news Credit: RTÉ News Archives

8. Richard Lee McNair

Since his initial arrest in 1987, McNair has escaped prison three times - with a variety of methods including using lip balm as a lubricant to slip out of handcuffs. But it was in 2006 that he had his most impressive escape.

McNair, who worked in the jail's manufacturing area, escaped by hiding himself in an "escape pod", fit with a breathing tube and buried under a pile of mailbags. The pallet was shrink-wrapped and moved to a nearby warehouse. When the delivery staff left for lunch, McNair cut himself out and escaped.

Hours later, he was stopped while jogging on a railroad track by a police officer. McNair had no ID and told the officer his name was Robert Jones, and was let go after he convinced the officer he was in town to help on a post-Katrina roofing project. He was added to the America's 15 most wanted list, and fled to Canada. After surviving by stealing cars and using a fake driver's license for a year, he was eventually found and arrested.

Richard Lee McNair Credit: U.S. Marshals Service

9. Escape from death row

In May 1984, in the Mecklenburg Correctional Center in Virginia, six inmates were on awaiting their execution by electric chair. After observing correctional officers being complacent in their procedures, they decided to make a move.

One inmate hid in a restroom until a CO left their cell block, before he charged out through the open door. He overpowered the officer and released the locks to all the cells in the block, freeing his fellow inmates. They took over the unit, stealing uniforms of other COs who entered when it was time for their shift.

They exited the building by putting on riot helmets and pretending to carry out a bomb, which was actually a TV placed on a stretcher, covered with a blanket . They placed the "bomb" in a van and drove out of the prison. Upon exiting they split up into different groups. Four were apprehended within a day, while the others were caught two weeks later.

Lem D. Tuggle arrest Credit: Clement Britt

10. Joaquín "El Chapo" Guzmán

Guzmán, a drug lord who went by El Chapo, was known for his ability to elude capture after breaking out of prison in 2001. He was on the run for 13 years before he was arrested, at which point he began his year-long plan to break out. He escaped from a high-security jail near Mexico City in 2015, despite the fact he was wearing a monitoring bracelet and had cameras facing him 24 hours a day.

Guzmán was last picked up by security cameras at around 9 pm as he prepared to take a shower in his cell, which gave him a short wall for privacy. After not seeing him for 25 minutes, the guards investigated, finding that in the floor of his shower was a 33-foot-deep hole.

The hole dropped into a tunnel, which was equipped with lights, a ventilation system, and a motorcycle on rails to take him away. It lead to a construction site a mile from the prison. Guzmán, who has an estimated fortune of a billion dollars, is suspected spending up to $50 million on bribes, so that the guards would ignore the construction work and delay reports of his escape.

El Chapo escape tunnel Credit: Getty

I don't know about you, but I wasn't expecting real-life jail breakouts to be quite so elaborate. Some of the entrants on this list could have done some really great work if their intellect was directed towards something more productive, but these attempts are fascinating nonetheless.