Prison Escapes That Went Horribly Wrong
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Prison Escapes That Went Horribly Wrong

We might start with a positive – not for
the authorities of course – and look at prison escapes that went marvelously right. We might remember one of the greatest escapes
of all time, and that was because it involved three men breaking-out of Alcatraz Prison. They went missing in 1962, and still no one
knows if they survived or died in the waters of San Francisco Bay. Then you have the final escape of Henri Charrière,
aka, Papillion, which involved sailing away on a makeshift raft. Or what about the numerous, incredibly cunning
escapes of the serial-killer scoundrel, Charles Sobhraj, a man we have talked about already
at length. More recently we saw the brazen escape of
the gangster Joaquín Guzmán Loera, aka, El Chapo, but like many escapees he was recaptured. Let’s now look at failed escapes: The Hapless Hitcher
Obviously, once you’ve managed to escape from jail or prison you should be careful
who you talk to as suspicion from another might land you right back in jail. In 2018, the BBC reported that 31-year Allen
Lewis was being taken from Greenup County Detention Center in Kentucky, USA, when he
told officers that his handcuffs were too tight and were hurting him. As an officer tried to help Lewis, after a
short struggle he made a run for it. Freedom at last! But the man was stuck on a highway and needed
a ride. In desperation he held out his thumb and a
kind driver stopped for him. Except the driver noticed that Lewis was trying
to hide what seemed like handcuffs fastened to one wrist. It turned out that the man driving the car
was a police officer himself. Lewis got a ride right back to jail. The authorities later said, “He thought
he was getting a ride, and he did.” You might call this guy a chancer, but we’ll
get around to some hardcore criminals who orchestrated amazing escape attempts. An Explosive Letter Writer
This is yet another failed prison escape attempt in 2018. This time it involved a man called Sean Damion
Castorina and he was trying to break-out of Alamance County Detention Center in Graham,
North Carolina. Serving time for first-degree murder, Castorina
wouldn’t have been released for quite some time, so he tried to figure out how he might
get out a bit faster. His cunning plan to expedite his sentence
was to build an explosive and blast his way out. Well, he needed help for that, so he wrote
a letter to two of his friends with information about how to make a bomb and which prison
wall they would blast – near to where Castorina would be waiting. What could possibly go wrong? Well, he sent that letter with bomb-making
information to the wrong address and it was picked up by a regular sort of person who
subsequently informed the authorities. The media later wrote, “He has now been
charged with four counts of felony conspiracy, two counts of manufacture/assemble a weapon
of mass destruction, and one count of attempted escape from jail.” Reading Between the Lines
Be careful what you say when planning a prison escape, even if you think your words are coded. In 2010, a 67-year old prisoner at the Isle
of Wight’s Parkhurst prison in the UK thought he would send a message to the outside via
a letter. In the letter these words were written: “More
heat, less light.” It sounds innocuous, but guards that were
monitoring all the prison mail became suspicious. It turned out that this former science teacher
had been hatching a plot to escape from what some people have called the “British version
of Alcatraz.” Seeing that the prisoner had written more
heat in one letter, the guards heated up some of his correspondence. This revealed that he had been using dried
lemon juice to write down his escape plans. The heat showed he’d sketched detailed maps
of the prison, while messages were conveyed using encrypted code and messages hidden in
Sudoku puzzles. He was also planning to use a helicopter to
pick him up in a part of the prison where it could land. He was found out. Later the prison governor said,”I am delighted
at the way our security team and Hampshire Constabulary have foiled a possible escape
attempt.” He was then moved to another prison, but reports
state that none of his accomplices were arrested. Love Won’t Tear Us Apart
This one should be a Hollywood movie, if it’s not already and we don’t know about it. It’s the story of a woman called Barbara
Ann Oswald. In 1978, she hijacked a helicopter that she
had charted, except she didn’t count on the pilot being an ex-Vietnam vet. She put a gun to his head and told him to
head to United States Penitentiary, Marion, in Illinois. She was trying to help inmate Garrett B. Trapnell,
a con-man, career-criminal and air pirate. Oswald was the lover of Trapnell and the two
had planned to get married. She didn’t get very far as the pilot of
the helicopter wrestled the gun from her and shot her in the head. That was the end of her and the end of the
escape attempt. But the plot thickened. The daughter of Oswald was convinced that
Trapnell was her father (he wasn’t) and she very much wanted to get him out. She was only 17 years old when she hijacked
TWA Flight 541 just months after her mother had died in her attempt to get Trapnell out. The brave daughter held the 80-something passengers
for hours and flew to another location with about 40 passengers. She had said she had dynamite strapped to
her chest, but the three sticks turned out to be flares. She was finally arrested. Trapnell, who had hijacked a flight himself
in the past, said there was no way that the young Oswald was his daughter. He’d never even met her mother face-to-face. Lord ‘Couldn’t Keep His Mouth Shut’
Over in Australia three hardened criminals who were all serving long sentences for drug
trafficking got the idea to hir e an SAS soldier living in the Philippines to get them out
of prison in Melbourne. Except a man called Lord Tony Moynihan got
in the way. Don’t let the Lord title fool you, this
man had once run a brothel, he had trafficked drugs himself, and he later grassed on others
to reduce his own time in prison. One of the people he grassed on was the man
known as Mr. Nice, aka Howard Marks, the Oxford educated global pot trafficker who later became
a celebrity of sorts. Anyway, so our Lord told the authorities that
he had learned that the three Ozzies had hired an SAS guy to land on the tennis courts of
the prison in a helicopter and break them out. He also said once they were dropped off they
would be taken in a van to Sydney and then they would board a yacht and sail into the
sunset. None of that happened as the cops just waited
for the men to wait on the tennis court and then arrest them during the escape attempt. Again, this could be a movie, and one of the
guys who tried to escape has been featured in books. His name is David McMillan, another well-to-do
Brit who speaks the Queen’s English, but trafficked drugs for a living. He not only became one of the world’s biggest
smugglers, but he is the only man, ever, to have escaped from Thailand’s notorious Klong
Prem Central Prison. He wrote a book about this called “Escape”,
saying because conditions were so brutal in Thai prisons and the fact he’d get death
likely reduced to life, he had no choice but to get out early. The Human Stain
Ok, back to criminals we might not label with the epithet “mastermind.” In recent years you can see that quite a few
prisoners in Brazil have successfully escaped from prison by crawling into and out of sewers. This can be a messy business of course, but
one can imagine the smell of feces can be put up with when the sweet smell of freedom
is just around the corner. But in 2016, things didn’t go as planned
for one fella. You can find a video of him online being pulled
back out of a clogged sewer in what the media only said was a Sao Paulo Prison. The video shows the captured man later standing
in his cell, his skin painted brown, a coating the Telegraph newspaper called, “human filth.” Current Status: On the Run
All of you out there know very well that if you were ever to successfully breakout of
jail or prison then the next best thing is probably to keep your head down. Right? We mean, you wouldn’t post a photo on Facebook
of your free face? No way. And you certainly wouldn’t post a picture
of your free head and not do anything about that globe icon that ensures anyone can see
this picture…Well, CBS news in 2010 reported that a man called Chris Grego did just that,
and he was wanted by police. This one is perhaps a bit of a cheat as Grego
managed to evade cops before he was actually sentenced for assault, so it’s more of an
escape from law than a prison break. We just like the story. While Grego was out he kept updating his Facebook
page, and so cops didn’t have to try very hard to find him. Grego had even showed off, posting his own
wanted poster on his page. One of the arresting officers told the press,
“If it wasn’t for criminals like him our job would be a lot harder.” Almost Perfect: 9/10
Sometimes we can be brilliant, and occasionally we just fall at the last hurdle. That’s fine, at least we got to that hurdle. But in this case you might wonder if the guy
could have pushed himself just that little bit further. His name is Robert Emery, and he was locked
up at Oregon State Prison in 2010. The Oregonian newspaper tells us that this
hardworking man, “broke windows, drilled out a door lock, broke into metal tool cages,
bashed a hole in the laundry wall, lugged bags of tools, dug under one fence and climbed
over another.” He’d also left a dummy in his cell, something
we often see in movies. The media reports that he had spent time making
this figure, so it would look just like a real sleeping person. It had been a physically demanding night,
and the news tells us that Emery wasn’t just tired but he was bleeding, too. Emery, then 50 and serving time for robbery,
kidnapping and assault, after being hurt on the razor wire fence then just decided to
catch a few ZZZZs. He got under a blanket and went to sleep in
the yard. Some reports, perhaps bordering on click bait,
state he fell asleep as he was just so tired. More responsible media, however, say he actually
gave up as he could not scale the razor wire fence. Watch Your Weight
While you could argue it isn’t the worst prison in the history of the world, the Tower
of London evokes nightmarish pictures of bodies being torn apart on the rack, of hellish screams
coming from dank chambers, of cruel leaders leaving anyone they disliked there irrespective
of any crime being committed. But people escaped, and as late as the 20th
century when a man picked a lock with a spoon. In the early 18th century the Earl of Nithsdale
dressed up as woman and managed to get past guards. For that trickery he saved his own head. In the 16th century Jesuits John Gerard and
John Arden performed the tried and tested rope over the wall thing, and managed to lower
themselves down to freedom. It’s said they did this with mangled hands,
a punishment hors d’oeuvre before they were really hurt. But this is not a show about success, and
we must tell you about Gruffydd ap Llywelyn, the son of a Welsh King back in the 12th and
13th centuries. He was imprisoned in the Tower of London after
some disagreement with the King of England, with the latter not keeping his end of a bargain. It’s said the king put Gruffydd up as a
“guest” in the tower, but the Welshman wasn’t keen on the idea. In 1244, he made a rope out of cloth and bits
of sheets, and then he tried to lower himself out of a window. His makeshift rope snapped – we are told
he was a portly man – and he fell to his death. And that’s all we have for you. Can you add to this list? Which one was your favorite? Tell us in the comments. Also, be sure to check out our other show
Man so Violent Even Other Prisoners Fear Him. Thanks for watching, and as always, don’t
forget to like, share and subscribe. See you next time.

About James Carlton

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100 thoughts on “Prison Escapes That Went Horribly Wrong

  1. "Preparation only takes you so far, after that, you have to take a few leaps of faith." – – Michael Scofield

    … sorry – you leaped in the wrong direction… 😂

  2. don't the police in the jail that help don't they check the letters of what writing is on i know its private for the prisoner but they need to check

  3. Yay! The Isle of Wight makes one of these lists – I remember this story, though even when the inmates manage to break out, they rarely get further than the nearby forest… it's an island, there's not a lot of chances to get away unnoticed…

  4. the greatest escape is definitely the 1962 alcatraz escape of frank morris and the anglin brothers. they we’re geniuses ❣️

  5. That guy opened someone else mail is that not a federal crime?
    don't get me wrong he did the right thing but still, it had someone else name on it and that's illegal

  6. The Only Thing You Can Do Dont Escape Because You Will Get Karma And Think About Lord And Say Sorry What You Did And Apologize From Your Heart Not Just Because You Say Sorry You Will Freely Go..No..Because You Need Patient..

  7. Dude: only an SAS soldier could escape…
    Me: are you sure? I know someone who can, hand over the word SAS please? draws on SAS

    Word: SANS

  8. lol!!!!!!!!!!!!
    To all the people who failed because they were not smart😂😂😂😂😂😂😂😂😂😂😂😂🤣🤣🤣🤣🤣🤣🤣🤣🤣🤣🤣🤣🤣🤣🤣🤣🤣😆😆😆😆🤣😂😂😆🤣😂😆🤣😂😆🤣🤣😂😆😂😆😂😆😂😂🤣😂😂😂🤣🤣😂

  9. It was 4 men in the Alcatraz prison break but the 4th guy didn’t make his hole big enough.

    That’s right isn’t it? I’m pretty sure but I need someone to make sure.

  10. “Let’s start with the positive side…”

    *starts with terrible criminals escaping jail to haunt us again*

  11. The Alcatraz ecapees actually survived.. A documentary was released showing letters they sent and pictures from Brazil in the 70's

  12. Quick update on the Alcatraz escapees 1 has been identified after a number of decades on the run he wrote a letter to the fbi giving details only the prison escapee could have known abbou i beleve he died at 82 from cancer

  13. Why can't these American Narrator's correctly pronounce English, Welsh and Scottish names? It's so cheesy I should do the narration! Dr David "Indiana Jones" Taheri

  14. One prisoner attempted to dress as his wife to escape prison. They only problem was that he didn’t practice wearing high heels, so the guards were suspicious of his clumsy walking

  15. the alcatraz escape is actually not a succesfull one, since they all died… national geo or discovery did a documentary about that, wether it was possible for them to survive, they even recreated the same boat out of rainjackets, and they also looked back at what the current was on that day and year, and there was only one explanation they either drowned because of failure of the raft , or they got swept out to sea because the current wouldve taken them out to the ocean 🙂

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