Top 5 Interesting 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. Interesting

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.

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.

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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.

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.

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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.

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.”