Top 10 Jailbreaks that Ended Badly

Many people seem to be unaware of a fascinating and obscure aspect about prisons: they are extremely difficult to break out of. This may appear arcane and enigmatic, but it's true. They construct those structures in order to keep people inside. Guards, walls, snipers, barbed wire, fences, moats, guard dogs, cameras, floodlights, and even seas are all designed to keep inmates contained until the system says otherwise.

Despite this, every year there are more attempts at escaping from prison than you can count. Most of these attempts, predictably, end up looking like trying to get a shot past Dikembe Mutombo in a Geico commercial. Inevitably, a guard will stop you, waggle his finger, and say, "Not in my house." This results in a lot of failed prison escape attempts, and we've compiled a list of ten of the greatest that went horribly wrong.

10. The Tunnel to Hell

When prison officials discovered Richard Matt and David Sweat's 2015 cinematic escape from the Clinton Correctional Facility, they became renowned. A pair of prison guards smuggled chisels and drills into the inmates' hamburger meat, which they then used to excavate a long and intricate tunnel leading to a drainage pipe. They freed themselves by exiting through a manhole.

The episode was rightfully linked to the movie "Shawshank Redemption" by news publications. Sweat would respond, "Shawshank ain't got s— on me," if he heard this. And he is correct. The escapees in "Shawshank" live out the remainder of their days in peace. Matt and Sweat were both found within a few weeks of each other. Matt was fatally shot. Sweat was apprehended, his sentence was lengthened (to nearly a life term), and he was ordered to repay the prison about $80,000 in repairs.

9. Dillinger Escape Plan

One of the most famous gangsters in American history, John Dillinger, is considered as both a violent mobster and a Robin Hood-like folk hero. Since his death, his legal struggles have become legendary. It is undeniably true that Dillinger was able to elude capture twice. He lost his life as a result of it.

Dillinger fled from Lake County Jail in Indiana in March 1934, using a wooden rifle he built in his cell. He was able to escape the prison quickly and without firing a single shot by intimidating the guards with the phony firearm. While that may not sound like things went horribly, it was Dillinger's successful escape that prompted officials to explore returning him alive. Dillinger was shot dead outside Chicago's Biograph Theater in July of that year, less than five months after his breakout, after viewing a movie with his lover and a companion.

8. Caught White-Handed

Kenneth Burnum tried to flee the Hamilton County Jail in Tennessee in 2013. His intention was to just stand in for another inmate who was scheduled to be freed that day. When the name of the releasee was read out, Burnum walked forward. He identified himself as the man, signed all of the proper paperwork, and even claimed the man's belongings. He was almost finished when he hit a snag. Officers noticed that the prisoner set to be released was black at his last stop. Burnum had a very white complexion. Burnum's sentence was lengthened, most likely because of the allegation of idiocy.

7. Finally: the Guard’s Cabin

In 2011, James Edward Russell was incarcerated at the Olympic Corrections Center north of Forks, Washington, for the fourth time. He resolved to try a daring escape in the middle of the night—and he succeeded. He got it out of the detention complex and into the woods, appearing to be on his way home.

He discovered a cabin in the woods and knocked on its door shortly after midnight. Russell asked to use the phone when the cabin's renter answered. There were only two issues to deal with. Russell was still dressed in his prison garb. Two, the man who rented the cabin worked as a guard at the same facility from where Russell had just escaped. Russell was rated an escape danger after his arrest and was transferred to a higher-security institution.

6. Officer Gravity on the case

Jessica Boomershine was sentenced to prison for kidnapping and robbing an elderly man who was 85 years old. She broke into the old man's home, forced him to withdraw money from an ATM for her, and then locked him in his car's trunk outside a landfill. So don't feel bad if her attempt at eluding capture failed miserably.

Boomershine attempted to flee a Prosecutor's Office holding cell by climbing into the ceiling and crawling through the tiles to freedom. She only got it a few feet up there before the roof caved in beneath her and she was forced to descend. She gently descended from her elevated escape route... straight into a garbage can, amidst the falling tiles. Given where she left her victim, it's poetic.

5. What a Garbage Plan

Sidney da Cruz and Carlos Pereira attempted to flee the Brazilian Delegacia de Furtos jail by simply being thrown out with the rubbish. As simple as a half-eaten pie. They hid in two garbage bags among the uneaten food and soiled plates until their lunch break was done.

When a prison officer approached the bags to remove them, he noticed they were trembling. That's a little annoying since, as any human with a functioning brain knows, pretending to be inanimate objects entails staying still. “At first I assumed there was a mouse, but on closer inspection, I could see it was two inmates disguised as bags,” the guard who discovered them said.

4. The Daughter Mask

Clauvino da Silva, the leader of the Red Command drug trafficking gang, devised an escape plan that was equal parts brilliant and ridiculous. He tried to flee Brazil's high-security Gericinó prison by dressing up as his daughter, masking her face, and exiting via the front door.

When his adolescent daughter paid him a visit, she brought him an outfit of her own. It's unclear where the mask came from, but it's as convincing as it is creepy. Silva put on his daughter's clothes, put on the mask with the long black hair, and tried to go out the same way his daughter had come. It's unclear whether his daughter was complicit in the plot or simply thought her cooky father needed some teenage female attire. In any case, Silva intended to leave his daughter in his place. Clearly, this was not the smartest plan in the world. Silva was apprehended, and the clip of them forcing him to re-don the outfit while laughing is funny.

3. Half Ain’t Bad, I Guess

During the American Civil War, prisoner-of-war camps were deplorable. In overall, the situation was horrible. Overcrowding, a lack of food and clean water, and sickness plagued the camps. Historians have compared them to Nazi camps on numerous occasions. That's why, in 1864, 109 Union POWs tried to flee the Confederate Libby Jail in one of the greatest prison breakouts in US history.

Only 59 of the 109 escapees made it to the Union line's safety. The remaining 50 people were not so fortunate. Two people drowned while attempting to swim across the James River in the area. The majority of the remaining 48 were sent to Andersonville Prison, also known as Camp Sumter. Andersonville was far worse than Libby in terms of the depravity of its conditions.

2. Ted Bundy… Succeeds

Ted Bundy's escape, unlike most of the others on this list, ended horribly because it was so successful. Bundy is a notorious serial killer who has kidnapped, raped, tortured, and murdered at least 30 people. Bundy was apprehended, but he escaped from prison twice. The second one lasted a long time.

Bundy went back to his old ways once he was free. He assassinated two young women and assaulted three others. If you want to read the gory details of the attacks, they are available to the public. In these, his final murders, he was brutal and vicious. Regrettably, they only happened because Bundy fled from prison and managed to avoid detection for months.

1. Can You Escape Alcatraz?

The 1962 Alcatraz breakout attempt by Clarence Anglin, John Anglin, and Frank Morris is still debated as the most famous prison escape attempt in US history. The inmates devised an amazing plan that began with them digging holes through their cell walls using discarded saw blades and handmade drills, which they concealed with cardboard covers and Morris' accordion music for six months. The trio escaped down their tunnels, out of the building, and onto the San Francisco Bay in a homemade rubber raft, their absence concealed by papier-mâché heads tucked into their blankets.

The FBI was unable to determine whether the men successfully negotiated the icy waters and made it to safety after an extensive search. They believe the males were most likely drowned. Since then, a continuous flow of tangible and circumstantial evidence has emerged, both confirming and disproving the men's survival. There have been other sightings of the men, mostly in the American south and in Brazil, but nothing has ever verified their continuous presence.

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