25 Dumbest Prison Escapes

Posted by , Updated on November 21, 2022

Have you ever given thought to how you would escape prison?

Most people would prefer not to be in prison (for obvious reasons). But it’s normal to think of worst-case scenarios and then imagine how you would overcome them.

Many people think that prison escapes are as simple as portrayed in movies such as The Shawshank Redemption or Escape from Alcatraz. However, those are just movies, and escaping from prison is no easy feat.

Truth is sometimes stranger than fiction … and more entertaining. There are many inmates in real life whose attempts to escape prison life are just downright silly.

Here are the 25 Dumbest Prison Escapes.


Guard noticed one small detail

At Hamilton County Jail in Noblesville, Indiana, an inmate tried to escape by posing as another inmate due to be released.

It might have worked except for one thing. The guy due for release was black, and the attempted escapee was white.


That darn social media


Chris Crego had a warrant out for his arrest because of a bar-room brawl.

Rather than stay in hiding, Crego thought it would be a great idea to post his location on Facebook. It wasn’t. It really wasn’t.


She's a federal marshal ... or not


When John Hayes wanted to escape prison, he had a female friend impersonate a federal marshal.

Needless to say, none of the prison guards believed her. Hayes got additional time on his sentence.


Bro, you only had to wait one day!

We understand that people can get impatient, but c’mon. All Andrew Wilson had to do was wait a measly 24 hours, and he would have been a free man.

Wilson escaped from a work camp in a truck. He was eventually captured and, needless to say, he was no longer eligible for release.


The Snoopy incident


Two men from New Zealand tried to break their friend out of jail with one wearing a Snoopy costume.

As it turns out, not only was this a horrible idea, but they went to the wrong prison.


A little excess baggage


Maria del Mar Arjona Rivero tried to free her contortionist boyfriend from jail by packing him in a suitcase that she had brought with her.

She expected that she could do this without anyone noticing. But they did, obviously.


Me mad, me punch door


A little word of advice. No matter how strong you might feel, you will never be able to punch down a prison door.

Somebody should explain that to Hector Campos. He tried to escape from a Florida jail by doing exactly that.

Needless to say, it didn’t work.


Never use a zeppelin, unless it's Led Zeppelin


When one thinks of a prison escape, they may picture using a helicopter.

One prisoner thought that helicopters were too obvious and decided to use an inflatable zeppelin to help him flee.

Sounds like a genius plot, right? The guards intercepted the inflatable zeppelin. After what we’re sure was a long laugh, they foiled the escape plan.


Sorry, no room


A few prisoners tried to escape from a Brazilian jail by knocking a hole in a shower. Two of those prisoners managed to get through, but when the last one tried to go through, he got stuck.

He cried for help but the guards decided to take pictures first.


The old "call the police on police trying to arrest you" trick


An escaped inmate and his friend called the cops on the cops that were chasing them.

The plan was to have the cops arrested for assaulting the escaped inmate and his friend.

The two were arrested and had plenty of time to think about how terrible that idea was.


His name was Mudd, literally!


Dr. Samuel Mudd was a famous doctor known for helping President Lincoln’s killer, John Wilkes Booth, with medical help during his run from the law.

Mudd was arrested and thrown in jail for lying about his connection to Booth.

When he escaped, he forgot something very important. Everybody knew his face, so he was arrested again.


Talk about impatient

In August of 2016, Christopher Boscacci broke out of a minimum-security prison. He had only been there three days on a petty theft charge.

Not wanting to hack prison life any longer, he climbed over a fence and got caught. Of course, he would have had to climb a few more fences than just that one.

The funny thing is, he probably wouldn’t have been in jail very long … if he hadn’t attempted a prison break.


Don't mind us ... we're just bags of trash.


Two inmates in Brazil tried to escape prison by climbing into full bags of trash.

They got caught because they began squirming around and an investigator thought a rat had gotten into the bag.

The two men were apprehended and put on garbage duty. Actually, we don’t know if that was their punishment … but it would be funny, right?


Oh sheet!

Prison breaks have been attempted and failed since forever.

In 1244, Gruffydd ap Llywelyn attempted to escape from a prison tower by climbing down a rope made out of a bedsheet.

The sheet broke because Llewelyn was too heavy, and he fell to his death.


Wanna hear a knock-knock joke?


Knock, knock.

Who’s there?

Escaped convict, knocking on a prison guard’s door.

Yeah, that’s not a joke but it did happen. James Russell had escaped from the Olympic Corrections Center. During his run, he spotted a log cabin.

The person who answered was a security guard at the prison from which Russell had just escaped. Russell was re-arrested.


Slammed by stupidity


Two inmates from New Zealand tried to escape from a courthouse while chained to each other.

They probably argued over which way to run, got caught on a pole, and stumbled.

As they tried to stand up and take off again, officers quickly arrested them … again.


The "no plan" plan

If you are going to use props to pull off a prison escape, make sure you know what to do with them.

Michael J. Norwood had a plan to break out of prison using a dummy, some rope, dental floss, and a few other items. It could have been a great plan, but Norwood had no clue how to use any of them.

Maybe he should have watched more prison movies.


Old McConvict


Curtis Ray Watson escaped from prison in Tennessee.

He was spotted on a farm and tried to get away on a tractor … not your fastest choice of transportation. He didn’t get far and was sent back to prison.


Hopping to get out


A prisoner by the name of George “Billy” Hunt tried to escape prison after dressing up as a skinned kangaroo.

He was captured after some guards mistook him for a real kangaroo, which they were planning to kill and eat.


Sir, where are your clothes?

A Japanese man had escaped from prison wearing just his birthday suit.

He was later found in an elementary school wearing a ski cap and a jacket.

That’s one strike for a bad prison break and another for poor fashion choice.


You're suppose to break OUT!


Most people break OUT of prison. One prisoner decided to go through great lengths to do just that.

However, once he was out, he decided that civilian life was overrated. Using a bed sheet, he climbed over the razor fence back to jail.


It's a lovely day for gardening


We’ve heard of some pretty insane ideas for prison escapes. But, this one takes the cake.

A prisoner tried to escape by burying himself in a prison garden. He was captured by a fellow inmate ratting him out.


The nunchuck escape


In Missouri, prisoner Lorenzo Pollard escaped by using homemade nunchucks to fight off guards.

Perhaps he should have thought more about eluding capture than fighting his way out; he was caught not long after.


Make sure everyone is on board


In all fairness, this failed attempt probably had more to do with bad luck than lack of skill.

Lester Burns and Michael Coleman tried to escape by stealing a van in which they were riding.

Unfortunately, another prisoner was with them, and he was not too keen on the whole escape plan. This prisoner called 911 and reported his fellow inmates as captors.


Dude, looks like a scary lady

This story gained national attention. A gang leader in Brazil tried to escape from prison.

How did he manage? Well, he dressed up as his daughter by wearing a silicone mask, a wig, and girls’ clothing.

The disguise didn’t fool anyone and he was sent back to jail.

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