America’s Greatest Prison Breaks (Part 1)


~Ricky Bobby

America has always had a fascination with escapes.  We make movies about escaping POW camps, our favorite game during Recess was Jail Break, and there was that one show on Fox that we only really watched for the first season, but apparently lasted for more seasons than Arrested Development.  There’s something American about sticking it to some sort of foreign land or domestic legal system(though we tend to have an easier time rooting for it when there’s a “Innocent person in jail” angle, but whatever).

Remember this?  No?  Nothing?

It is with the intrepid “this bird cannot be caged” American mindset, then, that we present you with…

AFFotD’s History of the Best American Prison Escapes

…Though Prison isn’t ALL bad…

The Libby Prison Escape Would Have Been More Famous If It Happened During World War II

We tend to forget that the Civil War had POW camps, since it’s a lot easier to focus on the whole “Brother fighting brother” or “Slavery” aspect of that whole war, but yeah, there totally were POW camps.  The Libby Prison was considered “inescapable” and covered an entire block of Richmond.  It was bordered by a river, with the actual Union prisoners being held on the third floor.  One area, flooded by the river, was called “Rat Hell” since it was infested with Rats, and apparently people wanted to name the room the worst possible thing they could think of, and we guess the name “Incest Murder Hole” was already taken.

“AGHHHHHHHHHHHHH”- photo unrelated

Eventually a few Union officers were able to gain access to Rat Hell by removing a stove on the first floor and making a passageway underneath.  In Rat Hell, they worked while “hundreds of rats” were constantly “squealing” which hopefully will be the most terrifying thing you will mentally picture today.  After seventeen days of digging, they eventually finished their tunnel, and took turns walking out in groups of two to three.  They resurfaced beneath a tobacco shed that was far enough outside of the main building that they were able to simply stroll out the front gate.

The escape was led by Colonel Thomas E. Rose, who did not successfully escape, being captured minutes away from reaching Federal lines.  Though to prove how badass of an escape artist Rose was, he was placed in solitary confinement when he was returned to Libby’s Prison, but was eventually traded back to the Union by the Confederates, who decided they didn’t want to have to deal with the precursor of Steve McQueen in The Great Escape.  109 Union soldiers escaped, with 59 reaching Union lines safely, and the remaining Union POWs received a much needed morale boost from the whole thing.   And with 59 successful escapes, the Libby Prison Escape was twenty times more successful than the so-called Great Escape, which didn’t even have the decency to involve any Americans.

John Depp Dillinger Escapes From Jail and Kills People, Whatever, He Does What He Wants

The year was 1933, and famous gangster and subject of an only-so-so-biopic, John Dillinger, had just finished an eight-and-a-half year prison term in Michigan City, Indiana, when he decided to rob a bank, because fuck you parole officer, that’s why.  When he was later apprehended in Lima, Ohio, the police found a document that basically amounted to “How I will break out of jail, by John Dillinger” on his person, to which Dillinger responded with a large shrug and a “I have no idea what that is, officer.”

We feel that we should point out at this point that John Dillinger had a prison escape plan on him…before he had even been arrested.  That’s basically the crime version of accepting an Oscar and then delivering a previously written and rehearsed speech.  He came prepared…to get arrested, which makes him about half Boy Scout and half…whatever the opposite of a Boy Scout is.

In a completely surprising move, John Dillinger eventually broke out of prison using the same plan that the cops found on him, at which point the policemen who found the prison break plan likely slapped their own foreheads and went, “Ohhhh, so those actually were his plans.”  Not the brightest cops you’ll see, evidently.

“Why yes, Mr. Dillinger, I WOULD like a beer.”

The prison break happened in several stages.  First, eight of Dillinger’s friends smuggled in shotguns to the Indiana State Prison, because, again, what the fuck 1930’s law enforcement?  After shooting two guards, three of these escapees went to the prison in Lima and informed the Sherriff that they were there to return John Dillinger to the Indiana State Prison for violating his parole with that whole “Bank robbery” thing.  When the Sherriff asked for their credentials, they said, “I got your credentials riiiiiiiight here” and everyone had a big laugh.  But, no, seriously, they shot him, beat him unconscious, and stole his keys.

“Ha Ha!”

They got Dillinger out of his cell, and locked in a deputy and the Sherriff’s wife in there (“Wait, wait, what was the Sherriff’s wife doing there?”  We don’t know, stop interrupting) leaving the Sherriff to die on the floor.  Dillinger went on to get captured again, but escape when his attorney smuggled in a wooden gun that he used to trick the guards into letting him escape.  Seriously.  Even though Dillinger was gunned down not too long after these shenanigans, he did go down in history for being one brazenly ballsy motherfucker.

The Texas Seven Was Like the Show Prison Break, Only With Less Tattoos And More Cops Being Killed (Maybe, We Didn’t Watch Seasons 2-4)


Having to face a long prison stay in the state with the itchiest finger on that Lethal Injection button can be a pretty daunting prospect.  With that in mind, George Rivas, who was serving 18 consecutive 15-to-life prison terms on charges of “To be honest we’re a little too terrified of the answer to look it up” came up with a plan to get out of jail, and take six inmates with him, who were serving terms ranging from 30 years to life.  While serving at a maximum-security prison in  Kenedy, Texas, the Texas Seven overpowered and restrained nine civilian maintenance workers, four prison guards, and three inmates who just got in the way of things.

Stealing a page from the “Sean Connery James Bond” book, the prisoners took the uniforms of the maintenance workers, and went to the back exit pretending to be installing video monitors.  They stole a stack of weapons, made some calls to the prison towers to distract them, and hijacked a prison truck to complete their escape.  So, it’s basically like Shawshank Redemption, except for the being innocent part, or the tunneling part, or the lack of beating the shit out of a dozen people.

So, basically, nothing at all like Shawshank

Having just gotten their freedom (while being the target of a nationwide manhunt), the Texas Seven did what any man would do when given a fresh taste of freedom.  That’s right, they…uh, held up a sporting goods store and shot up a cop?…Uh…yeah.  Not our first choice, but…we guess it’s someone’s first choice, clearly.  Eventually, they were captured through the help of America’s Most Wanted of all things.  One of the members shot himself during capture, while the remaining six were placed on Death Row.  Which sort of puts a bit of a damper on the whole “Oh cool, a prison break” side of things.

And with that, we’ve reached the halfway point of our look into the American History of Prison Breaks.  Stay tuned tomorrow for some Vietnam action, a tale that brings new meaning to the term “Like when that dude escaped from a Turkish prison” and, of course, Alcatraz.


One response to “America’s Greatest Prison Breaks (Part 1)

  1. Pingback: America’s Greatest Prison Breaks (Part 2) | affotd

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