Escaping from prison. Almost everyone thinks about it.

You’re looking at these razor ribbon covered fences or tall brick walls, and you want to be on the other side of them. It’s a cage, and anything caged wants to be free. Some would kill for it, some would risk dying for it. Some defy all the risks and make a break for it.

Every escapee knows one thing: fences and walls do not a prison make. Forget morality and justice for a moment: prison is a mindset and a competition between those who are armed and those who aren’t. Cars and steel, barbed-wire and concrete…any physical obstacle can be overcome, given enough time. These objects are there to slow you down until the people with guns can reach you. 

The escape method that seems most obvious is actually the most difficult. You are not going to dig a long tunnel to freedom in a standard prison today, except maybe at an outdated low-security one. Is it because of the cell-inspections by guards who may discover it? Somewhat. Is it because of a lack of proper tolls? To a degree. But mainly it’s because of the dirt.

While jails often only have one outer wall separating you from freedom, PRISONS are almost always constructed with fences hundreds of yards away from any building you may find yourself in for long periods of time. Tunneling out from your cell, you cannot flush that much dirt, and you can’t do what Andy DuFresne did in The Shawshank Redemption and drop handfuls at a time on the yard through a hole in your pocket. We’re talking years of work, and that’s if you can move a cubic-yard of dirt a day. And what happens if it rains?

Still, it happens.

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One man spent over a decade tunneling out of prison…so long, his sentence was nearly over by the time he completed it. Having invested so much time in it, he decided to go for it anyway, was promptly caught and given years added on to his sentence [1]. In another prison, a group of inmates tunneled outside of the fence from their cell block in a relatively short amount of time. They made it to the other side, poked their heads out, saw they had made it to freedom…then decided to go back to their cells and collect resources (clothes, money, food) and escape the next day. The hole was discovered in the meantime, bringing in the Department of Corrections elite “Emergency Response Team” and state police to take control of the prison [2]. 

Fences merely slow you down until people with guns can surround you. Those people cannot be everywhere, all the time…this knows the person planning to escape. How do you get over, or through, the fence quickly enough when no one is looking?

Some prison athletes are just. That. good…These fearless individuals make a dash for it, climb as fast as they can, weave between the razor-ribbon, endure tears in the skin, and get over the fences before anyone in authority can respond. However, usually there’s a trick: some have used thick blankets to partially cover razor-ribbon; some have made a “suit of armor” from magazines or tin-cans to protect themselves while scaling the fences [3]. They wait until the power is out, or have an accomplice disable the prison generator.

Some use grappling hooks made from the same materials that other inmates make shanks from, along with ropes made from braided bedsheets. Some manage to obtain bolt-cutters, either smuggled in or stolen from the prison’s maintenance division. Some assistance is given from the outside, from gang members/associates/family: one prison had an AK-47, along with some handgrenades, thrown over the fence and into the yard…though an alert guntower officer saw this and aimed his rifle at anyone who dared to go near them [4].

If you’re going to escape, it’d be a big help to begin outside of the prison already, wouldn’t it? MOST prison breaks aren’t actually prisoners escaping from a fenced-in prison; they’re technically just “unlawfully fleeing from custody”. The vast majority of escapes aren’t the exciting ones you see in movies: they involve minimum-security prisoners with relatively short sentences who are already working outside of the fences, who simply take off running when they feel there’s a good opportunity (often because their girl is leaving them, or they are about to face new changes).

Almost as common are prisoners escaping during transport between prisons or a courthouse, or at some point while on a medical transfer to a hospital. There are adrenaline-pumping moments where someone overpowers a transport-guard and takes his/her gun [5], car-accidents where someone accidentally hits a transport van and the door just pops open…and something as simple as a lifer fleeing the MRI-room at a local hospital because no handcuffs or chains can be worn near the machine.

Creative attempts occur sometimes that don’t fall into these categories. A helicopter, hijacked by a girlfriend at a small-airport flight school, was used to lang in the prison yard and break one man out [6]. A lifer named Rocky, slightly built and effeminate, grew his hair out long, stole a nurse’s scrubs, used Kool-Aid as makeup and impersonated a prison nurse, walking right out the front door (he was caught in the parking lot when an officer on shift-change noticed his inmate-issued shoes). A semi-truck, used for delivering supplies inside the prison, was taken over by three inmates who attempted to drive it through the main sallyport gate (two were shot, the third surrendered) [7]. 


After just coming to prison, I was approached by a short but athletically-built man named Lil Dan. Lil Dan had watched me for a while, knew I had a prison-bit to do, saw I was no rat, and figured I might want to “get out early”. He asked if I’d be interested. I was.

“What’s the plan? And what do I need to do?”

“Alright, we’re going to get some real clothes, some greenbacks, and a shank.”


“Then, you know the fence?”


“Well, we’re going to climb it.”

“Okay, how?”

“On a foggy day, we’re going to ‘book it’ to the fence, and then just climb over it.”

“That’s it?”

“Yeah, it’s so simple, it has to work!”

(I passed, but wished him luck. Lil Dan convinced a young man who was going home in about a year to attempt this ingenious escape with him. They were seen “booking it” to the fence by a patrol-guard on the other side of the fencing, and they made it to the fence to find a shotgun pulled and aimed at them before they even touched the chain-links) [8]

Most escape attempts are literally THIS stupid. Prisons deal with them on a somewhat-regular basis. Other ideas that have been proposed to me or considered at the beginning of my bit:

  1. Using easy-access to the roof of a building built on a hill overlooking the fence, there was consideration of a plan to sew multiple shirts and coats together to make a parachute for the heavy Autumn winds to parasol us to freedom.
  2. Testing the viability of using natural gas from the prison’s kitchen to fill layered garbage bags to see if enough of them could float us to freedom (they didn’t create enough left).
  3. Befriending and encouraging a fellow convict who was in prison for document forgery to see if he could make a convincing fake prison-identification card (he only made one side, and it was only convincing if you didn’t look at it closely). 

Jeez, no winter I never made it out. By now I’m shortly about to be released legally, so I’d have to be a complete moron to think like this anymore. But I did for a period of time, and I am the norm among prisoners. It’s why fences and walls and bars and razor-ribbon exist. These things don’t sto anyone, but they sure-as-hell slow you down. When it comes down to it, only those with the speed at the right moment, and the audacity (or stupidity) to believe in that speed succeed.

It’s not a chess match…it’s a game of frogger, where cars are organized and work together. Everyone thinks about playing the game. Everyone. But the only prisoners who try are those willing to take the risk of getting smashed. For you do get smashed…you get shot, get many more years added to your sentence, and spend years–or the remainder–of your entire sentence in the Hole or in a maximum-security hellhole.