Top 10 Jailbreaks that Ended Badly

There’s a really obscure and interesting fact about prisons that many people don’t seem to know: they’re pretty hard to break out of. I know this must seem arcane and inscrutable, but it’s true. They really build those things to keep people in. Guards, walls, snipers, barbed wire, fences, moats, guard dogs, cameras, floodlights, even oceans—all are meant to keep prisoners in until the system says otherwise. 

Despite this, there are more attempts to escape from prison each year than you could count. Predictably, most of these attempts go about as well as trying to get a shot past Dikembe Mutombo in a Geico commercial. Inevitably a guard blocks you, wags his finger, and gives you a charmingly mischievous, “Not in my house.” This makes for a lot of failed prison escape attempts, and here are ten of the best that ended really badly.

10 The Tunnel to Hell

Richard Matt and David Sweat became famous when prison officials discovered their 2015 cinematic escape from the Clinton Correctional Facility. A pair of prison staff members snuck the convicts chisels and drills inside hamburger meat, which they then used to dig a long and elaborate tunnel that led into a drainage pipe. They exited it through a manhole, free men.

News outlets compared the incident to the movie “Shawshank Redemption,” and rightly so. Sweat, upon hearing this, would say, “Shawshank ain’t got s— on me.” And he’s right. In “Shawshank,” the escapees live out the rest of their days in peace. In the case of Matt and Sweat, they were both found within a few weeks. Matt was shot and killed. Sweat was captured, his sentence increased (past a life sentence, somehow), and he was forced to pay the prison back nearly $80,000 for repairs.

9 Dillinger Escape Plan

John Dillinger, one of the most famous gangsters in American history, is regarded in equal measure as a vicious mobster and a Robin Hood-esque folk hero. His battles with the law have become mythologized since his death. What is undoubtedly true is that Dillinger was able to escape from prison twice. And it cost him his life.

In March 1934, Dillinger escaped from Lake County Jail in Indiana using a wooden gun he had carved in his cell. By threatening the guards with the fake weapon, he was able to leave the prison easily and without firing a single shot. While that sounds like things didn’t go badly at all, it was this successful escape that caused authorities to reconsider taking Dillinger back alive. In July of that year, less than five months after his escape, Dillinger was shot dead outside Chicago’s Biograph Theater after seeing a movie with his girlfriend and friend.

8 Caught White-Handed

In 2013, Kenneth Burnum attempted to escape Hamilton County Jail in Tennessee. His plan was to simply take the place of another inmate set to be released that day. When guards called out the name of the releasee, Burnum stepped up.

He identified as the man, signed all the necessary paperwork, and even claimed the man’s possessions. He was almost out until he hit one little snag. At his last checkpoint, officers noticed that the prisoner set to be released was black. Burnum was in fact very white. Burnum’s sentence was increased, presumably for the charge of stupidity.

7 Finally: the Guard’s Cabin

In 2011, James Edward Russell was serving his fourth stint in prison at the Olympic Corrections Center outside of Forks, Washington. In the middle of the night, he decided to make a daring escape—and succeeded. He made it out of the corrections center and into the woods, seemingly home free.

A little after midnight, he spotted a cabin in the woods and knocked on its door. The cabin’s renter answered and Russell asked to use the phone. There were only two problems. One: Russell was still wearing his prison uniform. Two: the man renting the cabin was a guard at the very facility Russell had just fled. After his capture, Russell was deemed an escape risk and sent to a higher-security facility.

6 Officer Gravity on the Case

Jessica Boomershine went to prison for kidnapping and robbing an 85-year-old man. She broke into the elderly man’s house, forced him to withdraw money from an ATM for her, and then left him locked in the trunk of his car outside a landfill. So don’t feel bad that her escape attempt was an embarrassing mess.

Boomershine tried to escape a holding room in the Prosecutor’s Office by entering the ceiling and crawling through the tiles to freedom. She only made it a few feet up there before the ceiling collapsed beneath her—and she ended up down there. Among the falling tiles, she slowly dropped from her elevated escape route… straight into a trash can. It’s poetic, considering where she left her victim.

5 What a Garbage Plan

Speaking of garbage: Sidney da Cruz and Carlos Pereira attempted to escape the Delegacia de Furtos jail in Brazil by simply being thrown out with the trash. Easy as half-eaten pie. The pair waited until their lunch break was over and hid in two garbage bags among the uneaten food and dirty plates.

When a corrections officer approached the bags to take them out, he noticed that they were shaking. That’s a bit frustrating because, as any human with a working brain would know, staying still is a pretty part of pretending to be inanimate objects. The pair were discovered, and the guard who found them gave this beautifully simple account: “At first I thought there was a rat, but on closer inspection, I could see it was two inmates disguised as bags.”

4 The Daughter Mask

Clauvino da Silva, a Red Command drug trafficking group leader, hatched an escape plan that was equal parts genius and absurd. He attempted to escape Brazil’s high-security Gericinó prison by dressing as his daughter, wearing a mask of her face, and leaving through the front door.

When his teenage daughter visited him, she brought him an outfit of her clothing. Where the mask came from is unknown, but it is as convincing as it is creepy. Silva changed into his daughter’s clothes, donned the mask complete with long black hair, and attempted to walk out the way his daughter came. Whether his daughter was in on the escape attempt or just thought her cooky dad needed some teenage girl clothes is unsure. But either way, Silva planned to leave his daughter there in his place. 

Clearly not the best plan in the world.

Guards caught Silva and the footage of them making him re-don the costume while they laugh is hilarious.

3 Half Ain’t Bad, I Guess

Prisoner-of-war camps in the American Civil War were vile. In general, conditions were atrocious. Camps were overcrowded, lacked food and clean water, and were riddled with disease. Historians have repeatedly compared them to concentration camps. That’s why in 1864, 109 Union POWs attempted one of the largest prison breaks in U.S. history from the Confederate Libby Prison.

Of the 109 escapees, 59 made it to the safety of the Union line. The remaining 50 were not so lucky. Two drowned while attempting to swim across the nearby James River. Of the remaining 48, most were transferred to the infamous Andersonville Prison, aka Camp Sumter. Andersonville was even worse than Libby, and the horror of its conditions was unparalleled.

2 Ted Bundy… Succeeds

Unlike most of the escapes on this list, Ted Bundy’s escape ended badly because it was so successful. Bundy is infamous for being one of the worst serial killers in history, having kidnapped, raped, tortured, and murdered at least 30 people. Bundy was finally caught but escaped from jail (twice, actually. The second one lasted).

Once free, Bundy resorted to his old ways. He murdered two young women and attacked three more. The details of the attacks are public if you wish to read the gruesome details. He was violent and cruel in these, his final murders. Sadly, they only occurred because Bundy escaped from jail and successfully evade capture for months.

1 Can You Escape Alcatraz?

Perhaps the most famous prison escape attempt in U.S. history, the 1962 Alcatraz escape by Clarence Anglin, John Anglin, and Frank Morris is still the subject of debate. The inmates hatched an ingenious plan which first began with six months of carving holes in their cell walls using discarded saw blades and homemade drills, hidden with cardboard covers and Morris’s accordion music. Concealing their absence with papier-mâché heads tucked into their blankets, the trio escaped through their tunnels, out of the building, and into the San Francisco Bay on a homemade rubber raft.

After an exhaustive search, the FBI was couldn’t confirm whether the men successfully navigated the frigid waters and made it to safety. They believe that most likely the men drowned. Since then, an unsteady trickle of material and circumstantial evidence has come forth, both supporting and refuting the men’s survival. A number of sightings of the men have cropped up, mostly in the American south and in Brazil, but nothing has ever confirmed the men’s continued existence.