For some reason, people really don’t like being in prison, leading to a tug-o’-war for the ages between security experts and inmates who want the easy way out. The more inventive in the general population always find creative exits, though, and many of them can’t be said to be easy.

Richard McNair Mailed Himself to Freedom

Richard McNair

(United States Marshals Service/Wikimedia Commons)

Convicted murderer Richard McNair escaped police custody three times after his 1988 arrest, first by using lip balm to grease his way out of his handcuffs, then crawling out of prison through a ventilation shaft, then by sneaking onto a pallet of mailbags destined for the outside. He was actually shrink wrapped into the pallet, which he’d planned for by packing a breathing tube, then cut himself out and jogged away. He was actually stopped by an officer shortly afterward, but despite having no ID and giving two different names, McNair convinced him he wasn’t the droids he was looking for. He was free for a year and a half before he was caught driving a stolen truck, which you’d think you’d avoid on the lam.

 

While he was still on trial for being an all-around nightmare, Bundy was allowed access to a second-floor law library, where he noticed an open window one day while his guard went out for a smoke and simply dropped out of the window. Later, he embarked on a dedicated mission to lose 20–25 lbs. -- enough to fit through a hole he’d carved in the ceiling, which he used to enter the ducts and crawl into a guard’s apartment, steal his clothes, and bust out.

John Dillinger Threatened Guards with a Fake Gun

John Dillinger

(FBI/Wikimedia Commons)

In 1934, Dillinger was serving one of his many jail stints at the supposedly “escape proof” Crown Point, Indiana county jail when he apparently decided to take the claim as a challenge, whittling himself a wooden “gun” that he convinced the guards was real for long enough trap them, secure some real guns, and bolt.

The Escape From Alcatraz

Alcatraz escape room

(Benlechlitner/Wikimedia Commons)

The famed 1962 “Escape From Alcatraz” by three prisoners and longtime friends involved building dummies with real human hair whose origins we don’t want to know and a makeshift raft in a secret rooftop workshop. They successfully made it out, and though they were assumed to have died in the rough and frigid waters of the bay, no trace of them was ever found, and they could still be out there today. They’d be super old, but you don’t reach your centennial or escape from Alcatraz without some tenacity.

Casanova, a Priest, and an Iron Spike

Casanova escape

(Bibliothèque nationale de France/Wikimedia Commons)

No, it’s not the beginning of a crude joke. In 1755, Giacomo Casanova was arrested for being an affront to common decency, which is sadly no longer a crime, and pretty much immediately started planning his escape using an iron bar that he’d fashioned into a spike and hid in an armchair. He passed the spike inside a Bible under a plate of pasta to a fellow prisoner and disgraced priest, who helped him carve a hole in the ceiling of his cell and break free, but not before Casanova taunted his cellmate, who was a spy, into silence. And that’s why prisoners aren’t allowed armchairs or good pasta.

The Texas Seven

In 2000, a group of seven inmates at a Texas prison managed to take down a total of 15 prison workers one by one with the classic tactic of “distract them while someone else knocks them upside the head.” After tying up their hostages and stealing their clothes, the seven stayed hidden for over a year by living in a motorhome in Colorado and telling people they were Christian missionaries.

Lum You Just Walked Out

Lum You

(Unknown author/Wikimedia Commons)

In 1901, a Chinese laborer living in Washington named Lum You was sentenced to death for fighting back against and killing a white man who assaulted and robbed him. Even back then, everyone thought that was shitty, so two weeks before his execution, You found that someone had egregiously forgotten to lock his cell. He was recaptured after only three days, explaining that he’d just walked right out.

Peter Kropotkin Hid in a Fancy Restaurant

Peter Kropotkin

(Gallica Digital Library/Wikimedia Commons)

Activist Peter Kropotkin’s 1876 escape from a Russian prison wasn’t a quiet one, leading the guards on a foot race through an open gate. He managed to lose the fuzz, but they were combing St. Petersberg for him when a friend suggested hiding out in the city’s most fashionable restaurant, insisting it was the last place anyone would look for him. It worked -- he had a great meal with a bunch of friends and then fled the country.

In 1921, Victor Folke Nelson scandalized Boston by making a run for it out of Charlestown State Prison, using the bars on a window as a ladder to climb a 40-ft. wall and then jumping 10 ft. to the outer wall, all while dodging a hail of bullets. He dropped 30 ft. to the ground, and two nearby railroad workers actually watched him casually stroll away, but who would try to stop him at that point?

Yoshie Shiratori’s Secret Weapon Was Miso Soup

In the ‘30s and ‘40s, Yoshie Shiratori became famous for his repeated prison breaks, necessitating a series of increasingly secure facilities and thus creative methods. The tool that served Shiratori best was the miso soup prisoners were fed in Japan. First, Shiratori spat the soup onto the metal door of his cell to weaken the metal and then squeezed through by dislocating both of his shoulders, and on another occasion, he used the bowl to dig through the floor of his cell. What were they gonna do? Deprive a man of soup?

The IRA Straight-Up Flew Out

In 1973, three men were serving time in a Dublin prison for, you know, being in the IRA when a helicopter suddenly appeared out of nowhere and landed in the middle of the exercise yard one afternoon. It turned out to be their IRA-mates, who had hijacked the helicopter to lift them out of there like terrorist James Bonds while everyone just kind of stood around, trying to process unprecedented levels of audacity.

Joseba Sarrionandia Stowed Away in a Speaker

Joseba Sarrionandia

(Jose Goitia/Wikimedia Commons)

In 1985, singer Imanol Larzabal visited a Spanish prison, performing a sort of Basque Live at Folsom Prison. Inmate Joseba Sarrionandia, a Basque separatist and writer, saw this as a golden opportunity, and not just because he was a music fan. He and a friend hid themselves inside a loudspeaker that was used in the concert and let themselves be carried out by roadies who surely must have noticed that the speakers had gained “a whole human” pounds. Maybe they were just happy for the hazard pay.

Redoine Faid Exploded His Way Out

Redoine Faid, a French gangster “known for brazen attacks on cash-in-transit vehicles,” took a similarly ham-handed approach to jailbreaking by literally breaking the jail with explosives, blasting through five prison doors before anyone could stop him in 2013. It’s not clear how he got the explosives, but you’d think prisons would have people whose entire job was preventing those from getting in.

Zdzisław Najmrodzki Escaped 29 Times

Between 1974 and 1989, Polish ganger Zdzisław Najmrodzki managed to escape custody a whopping 29 times, most memorably by convincing his guards to get drunk with him and then walking off while they were passed out during his very first jail stint and knocking out an officer while still handcuffed before stealing his keys and ID to free himself and impersonate the officer in 1985. He was actually pardoned in 1994 but died less than a year later in a stolen car doing what he loved: a whole lot of crime.

Jack Sheppard Pulled the Oldest Trick in the Book

Jack Sheppard's body carried away

(Isaac Cruikshank/Wikimedia Commons)

Jack Sheppard was also a serial escapist, but his first attempt in 1724 was also his funniest. He’d lowered himself down from the roof with ropes made out of bed sheets, but he wasn’t very sneaky about it, so a crowd of people had formed outside before he could get away. To distract them, he shot off a quick “Hey, I think that’s him over there!” before running away. He managed to escape three more times before his execution by hanging, by which time he’d become so famous that he was actually killed by a group of fans who rushed forward to pull on his legs and make sure he died quickly, proving that crime doesn’t pay, even if it’s really, really cool.

Top image: Donn Dughi/Wikimedia Commons

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