Craziest Failed Prison Escape Attempts

From hot-footed, high-heeled escape attempts, to some very tight squeezes, let’s break down some of the craziest failed prison escapes ever attempted.

March 13, 2023・

10 min read

Going to prison isn’t at the top of most people’s bucket list. But for some people who do end up jailed, serving their sentence is the last thing on their minds. Unfortunately, their minds also seem to often lack a smart, fool-proof escape plan. But that doesn’t stop them from trying, often with outrageous and hilarious results.

From hot-footed, high-heeled escape attempts, to some very tight squeezes, let’s break down some of the craziest failed prison escapes ever attempted.

10. Pole Dancing Prisoners

In 2009, a dastardly duo found themselves handcuffed together for convenience of transport after a New Zealand court appearance. One had received a two-year sentence for assault and the other was up for parole violation and fresh charges of auto theft.

While cuffed, they came up with a daring escape plan in minutes. Of course, this wasn’t enough time to come up with a smart strategy. Their big idea? Make a run for it. They clearly didn’t put much thought into their chances of escape, or the likelihood of extending their sentences as punishment.

When they attempted to flee the courthouse together, they were immediately pursued, and pepper sprayed. This no doubt blinded them, which probably explains this moment of stupendous, slapstick stupidity.

It seems they chose the wrong time to go their separate ways: around a streetlight. Needless to say, their plan was foiled, and their freshly-slammed heads were sent straight to the slammer.

9. Helicopter Hell

In 1989, Benjamin Barry Kramer, one of Miami’s most prolific drug smugglers and money launderers, found himself in the federal Metropolitan Correctional Center in Florida. Prison life didn’t suit Kramer, who’d grown accustomed to living lavishly off the $48 million his criminal empire had amassed him.

So, with the help of his brother on the outside, Mark Kramer bought a helicopter, hired a mercenary-type and put him through ‘helicopter school’. However, the mercenary probably should’ve trained a little longer.

Trouble came when the mercenary lowered the chopper into Kramer’s prison yard, allowing Kramer to grab onto one of its skis. One of its propellers came into contact with the prison fence and the helicopter came dramatically crashing down.

Both were injured but seeing as Kramer was already serving a life sentence, he didn’t really lose all that much. In fact, he gained a pretty great story to tell in the yard, albeit with a slightly embarrassing ending.

8. Trash Talk

In 2012, two inmates at Delegacia de Furtos prison in southern Brazil attempted to escape in a pretty trashy way. They decided to hide in plastic rubbish bags and wait to be taken out with the rest of the garbage.

Unfortunately, the men had a severely unfortunate habit of fidgeting. An officer heard the bags rustling, and assumed it was a rat, only to discover a larger pair of mammals than he’d expected.

Security couldn’t believe that the inmates presumed plastic bags would hold their weight when carried out. Even if they did, the two geniuses had failed to consider how the unusually heavy, human-shaped garbage may draw unwanted attention. Sometimes, it seems, the trash takes itself out. Or, in this case, keeps itself in.

7. Run For Your Wife!

At 39 years old, Brazilian Ronaldo Silva found himself incarcerated for suspected drug trafficking. Understandably, he asked his wife for marital support by bringing him a few bits and pieces from home.

Only, his requests were a little unusual for non-drag queens. Silva’s wife obliged, bringing him female clothes so he could don the dress, wig, heels and painted false nails she’d provided. He’d even shaved his arms and legs to complete the look.

His wife left the prison herself wearing Silva’s shorts and another top she’d brought, and Silva soon followed. He reached the prison gates and even the bus stop outside, thanks to his gorgeously-girly new garb. But he never quite made it to the motorbike waiting for him thanks to one major issue: he hadn’t practised walking in high heels.

The guards patrolling the perimeter noticed his peculiar, unsteady gait and investigated. Up close, this wobbly-footed ‘woman’ wasn’t so pretty, and they picked him up and brought him back inside. And just like that, Silva’s cross-dressing days were over as quickly as they’d begun.

6. Bad Time For A Breather

If you’ve ever lacked the motivation to exercise, you’ve got something in common with attempted escapees Frank Arthur and Clayton Musselman. Only, your laziness probably didn’t have such a tremendous influence on your future.

In April 2017, having made detailed drawings of the exterior of Virginia’s Henrico Jail East, where they were imprisoned, Arthur and Musselman carried out their escape plan. Eluding guards, they ventured out into the exercise yard and attempted to make a break for it.

They knew the motion cameras would pick them up quickly, so they’d have to move fast and scale the fence without delay. When security was alerted by the cameras, they didn’t expect to see two men moving in what appeared to be slow motion across the exercise yard.

They used a bench to get up part of the fence and brought clothes to place over the razor wire. But both men were left gasping for breath, thanks to their shared lack of fitness. Really, you’d think someone with the surname Mussel-Man would be in better shape.

Despite the short length of their escape attempt, the men were soon exhausted, and gave up, sitting down and awaiting a recapture. After the laughable attempt, they were treated for their injuries from the razor wire before being thrown back in jail to face fresh charges. On the bright side, they’ll have plenty of time to catch their breath.

5. Hot-Pants Houdini Humiliated

In 2016, a Brazilian criminal saw a hole in the system and went for it… literally. When he was arrested for robbing a jewelry store, he decided it was better to attempt an escape at the police station than the prison he would soon be headed to.

So, he stripped off to his bold, purple undies and tried to squeeze through the food-tray hole halfway up his cell door. He made it past the shoulders, but his lower torso refused to be part of any further crime, favoring a more honest approach to the judicial system.

It seems Shakira was right; hips really don’t lie. In fact, his hips were straight-up narks and left him in even more trouble than he’d been in in the first place. It took a lot of sunflower oil to get him out, but at least he was well-moisturized by the end of it all.

4. Beaten By The Belly

In 2012, 16-stone Rafael Valadao had a similar, but a notably bigger problem. Having smashed a hole in his cell wall using a metal bar from a shower pipe, he made the mistake of underestimating his size.

But this was much worse than trying to squeeze your butt into jeans that don’t fit anymore. After all, that usually leads to embarrassment and self-loathing; not a fractured rib and a rescue by firefighters. But those latter two are exactly what Rafael received when he became stuck in his DIY escape hatch, while being laughed at by the officers.

He also had the further embarrassment of having blocked two other inmates from their escape too. The thinner inmate who climbed through first and escaped obviously took the farcical foursome’s only brain cell with him, as well as (presumably) a tape measure.

3. Nothing To Declare

We’ve all overpacked a suitcase at one time or another. But nineteen-year-old Maria del Mar Arjona took that to a whole other level when she was witnessed struggling to wheel her suitcase out of Chetumal Jail in Mexico.

The nervous-looking woman was stopped by the guards, who unzipped the bag to find her husband, prison inmate Edwin Valdemar Artiaga Perez inside, in just his socks and pants. Packing light, it seems.

Due to her being there for a conjugal visit – which is essentially state-certified slammer slammin’ time – she had been allowed to bring the suitcase. I don’t know how freaky people get in that part of Mexico but bringing a suitcase into the bedroom should probably have been a red flag for the guards.

Either way, Edwin is now serving the rest of his twenty-year sentence and Maria del Mar was herself detained. On the bright side, if they ever get out, they can celebrate with a cheap vacation. After all, flights are much cheaper when your husband flies in the cargo hold.

2. Fed Zeppelin

In 2009, an Italian drug trafficker attempted to escape from a prison in the Canary Islands with the help of some pretty sophisticated technology. A Ugandan and two Spaniards, prior to their arrest, were at hand to provide assistance for the escape.

600 yards away from the prison, the three set up a camouflaged tent to scout out the prison’s security measures using high-tech equipment. They had motion detectors set up around their tent to warn of any intrusion, but their plan was foiled by human error.

No amount of tech could help when authorities were tipped off and intercepted a very special parcel the unlucky accomplices had been waiting for. The parcel, which had been sent to the Canary Islands from Italy contained a 13-foot-long, remote-controlled airship.

The three men had intended to fly it over the prison, dropping night vision goggles, climbing gear and camouflage paint to their Italian on the inside. He would then – presumably – use the equipment to clamber over the prison wall at night and into a waiting car.

But of course, the police’s interception of the package led to the arrest of the two accomplices, so much like the airship, the plan never got off the ground.

Honorable Mention

In May 2010, wardens at a prison in the Isle of Wight, off the coast of England, encountered some truly bizarre intruders. The leader of the pair was attempting to break down a door, to gain access to the prison, all while dressed as Snoopy.

The intruders were trying to break a family member out of what turned out to be the wrong prison. To make matters worse, the correct unit was less than 1,000 feet down the road. This error only became apparent after some time spent hurling concrete and brandishing what later turned out to be a water pistol.

Despite the farcical hilarity of the event, it still shook up the wardens. The would-be jailbreakers, obviously not in great frames of mind, were held afterwards for mental health assessments. What would Charlie Brown think of all of this, Snoop?

1. Like Father Like Daughter

In August 2019, Brazilian gang leader Clauvino da Silva was spotted by guards as he tried to escape after visiting hours. His attempt was surprisingly well thought-out and involved his 19-year-old daughter, who smuggled in some very unusual items to help him.

Having swapped clothes with his daughter, donning her skinny jeans and t-shirt, da Silva popped on a wig and a silicone mask which completely covered his head.

Despite his new face, and the girly accessories and sandals to match, there were issues. Firstly, he didn’t move like a woman, which really made him stand out in light of the second issue. That second issue is that he attempted to walk out among a group of real women, so he stood out among them like a sore thumb.

So as not to draw attention to this fact, the women who were apparently in on the plan, attempted to group around him and hide him while moving. This proved to be counterproductive too, thanks to a facepalm-worthy lack of subtlety.

The guards grew suspicious as to what they were all visibly trying to hide, and soon uncovered the truth, foiling the escape attempt.

I hope you were entertained by these crazy prison escape attempts that only ended up in failure and humiliation. As always, thanks for reading!