Mr. Ronaldo Silva, drug trafficker extraordinaire and budding escape artist,
looks down at his smooth-shaven legs. He runs his hands across his shorn arms.
Just before he leaves his cell, he puckers his lips in the mirror.
Smiling, he thinks, “Today is a great day to become a woman.”
It was just another visiting day for the inmates at the prison in Penedo in the
northeast of Brazil, but for Silva, it was a make-or-break time in his life as a criminal.
He was about to commit himself to one of the most daring escapes on record,
and it has to be said, one of the funniest, too. Silva was looking at doing some serious time
behind bars; time he didn’t have to spare. That’s why he’d already attempted one escape,
but after that failed, he ended up getting a transfer to Penedo.
Security there was a bit stricter but not so thorough any of the guards noticed he’d
shaved all the hair off his legs and arms. He’d done his best with his face, but what’s a man
going to do when he has jet black hair. Silva didn’t exactly make the most convincing woman.
When he arrived at the visiting area, he was among a throng of inmates
visiting their nearest and dearest. Silva sat down across from his wife, still making
sure to hide the fingernails he’d already decorated with a rather fetching red varnish.
When the coast was clear, his wife passed a tube of red lipstick. He did his best to
apply it without the aid of a mirror. The prison might have been understaffed that
day because not only did his wife manage to pass him a wig, but the two exchanged clothes.
Silva slipped on her blue dress, and she donned his shorts. He tied the dress at the waist with
a black belt and buttoned it above his bra. Now there was just one thing left: footwear. He
wanted to look the part, but let’s just say he’d not had much practice wearing high-heeled shoes.
As the buzzer sounded for the end of visiting time, somehow Silva’s wife
mingled with the inmates, and he joined the group of visitors. Keeping his head
down but struggling to find his balance in those shoes, he walked right out of prison.
Outside, among scores of other women, he just kept on strutting. A wide grin began to form on
his face as he made it down the street. The next stop was the bus station. There, two men were
waiting on motorcycles to take him to his freedom. But as he picked up the pace in his excitement,
that manly gait of his became more obvious. People stared at Silva as he hobbled along
on those heels, his 5 o'clock shadow now looking very out of place with his clothes.
One of those who noticed the strange sight was a local cop, and he put two and two together.
Silva’s freedom didn’t last long. The cop put Silva back in handcuffs, and soon he was walking
back in the direction of the prison, although at that point, he’d slipped out of his heels.
As for his wife, she denied any part in the escape attempt, saying Silva had just demanded
her clothes. The warden didn’t believe that for a second, although he had to admit the entire thing
had been an embarrassment for the prison. He told the Brazilian media, “At the time
it was visiting hour and there were more than 150 family members inside the prison. But we're taking
measures to ensure this doesn't happen again.” You have to wonder, though, where Silva got the
idea to do such a brazen thing. We think we know.
In 1973, an American named Dwight Worker found himself in Lecumberri prison in Mexico City.
He’d been given a lengthy prison sentence for attempting to smuggle cocaine from South
America through to the US. After experiencing some astoundingly awful conditions in prison,
he made a plan to escape. There was just one problem, though,
the place was a fortress. The only inmate to have escaped before was the notorious Pancho Villa.
On a visiting day, Worker told his wife, Barbara Chilcoate, that he had to get out of the hell
hole, otherwise known as the “Black Palace.” It wasn’t going to be easy.
Worker, despite his bad decision to smuggle drugs, was a very smart guy. After buying the cocaine in
Peru, he used the knowledge he’d gained working as an emergency medical technician to build himself
a cast for a fake broken shoulder. He even went as far as making a bunch of counterfeit x-rays
should anyone question his injury. If anyone asked how he’d managed to
break his shoulder, he’d created a printout of a newspaper article
that talked about how this American guy had fallen while climbing up Mount Chimborazo in Ecuador.
That wasn’t a real article, neither were the hospital receipts he had on him,
which showed how much he’d paid to get himself fixed up. In Worker’s mind, cocaine-addled
as it was in those days, no cop or customs official would want to break open a man’s cast,
especially when he had all that documentation. He snorted a couple of rails in his hotel room
and started making the cast around his bags of high-quality cocaine. What he didn’t bargain
for is customs officials knew every trick in the book. They certainly were ok with breaking
open a person’s cast if they had the slightest suspicion underneath it lay the devil’s dandruff.
Fast-forward a year or so, and Worker was sitting in solitary confinement.
He’d already been stabbed, and he’d spent much of his time with murderers. He’d spent a total
of 41 days in solitary and had been in the prison hospital three times through injury and illness.
He later said, “I felt there was a real good chance I was not going to make this physically,
that I would be killed.” This is how he described the prison:
“At the back of dormitory A were people who had been completely forgotten,
had no visitors, were crammed 12 into a room of perhaps two meters by four meters.
They had missing eyes, missing fingers. I saw dry leprosy.
There were people who had been there for 30 years without seeing a judge.”
He said it didn’t matter one bit that he was an American. The embassy official told him
that he’d done the crime and he had to do the time, no matter how inhumane conditions were.
Worker talked about how he’d been stabbed and extorted, to which the official just said, tough,
this is what you get for trying to smuggle drugs. Worker knew about a law in Mexico called “La Ley
de Fuga”, which basically meant that if he was caught trying to escape, they had the
right to kill him. Still, he had to get out. Over time, his wife smuggled in women’s makeup,
which he used to practice making himself look like a passable woman.
On the day of the escape, he applied a lot of foundation to his face and put on some lipstick.
He already had a wig that his wife had smuggled in, and he had a dress.
He also had a pair of high-heels which he said weren’t easy to walk in at all.
On the big day, he used a visitor’s pass as well as his drag suit to get outside the prison.
He then met up with his wife at a designated spot and later took a bus to the border of Tucson,
Arizona. With the help of some fake documents, he was soon on American soil once again.
Worker later became a professor, wrote a book, and has appeared on TV a few times.
So, it seems escaping prison dressed as a woman can work. You probably need a bit of
practice wearing high heels, although we think a good amount of luck is required.
You also need a good outfit. Perhaps no better outfit has ever been made than the one used by
the next man we are going to talk about. His name was Clauvino da Silva.
Nicknamed “Shorty,” he was somewhat short in stature, although this helped when he tried to
escape a Brazilian prison in 2019. He not only had a wig, a bra,
a teenager girl’s top, but he’d got his hands on a silicone mask in the style of a young woman.
Da Silva certainly looked the part, although his uncanny female mask was maybe a bit too
distressing to pass as believable. The guards pulled him up, and his cunning plan was thwarted.
Still, facing a 73-year prison term for a drug offense,
it’s no wonder he planned an escape. His 19-year old daughter was in on it,
of course, and she was later charged with aiding a prisoner’s escape attempt.
It was she and some other relatives who’d brought in all the necessary items.
You can’t blame a girl for trying to help her father, especially given that he was
not due out of prison until his hair turned gray. The last thing you’d expect, though, is a family
member in prison turning on another family member. That happened in Peru in 2016. A young man named
Alexander Delgado was serving 16 years when he got an idea of how to escape.
It required the unwitting help of his loving twin brother, Giancarlo. Giancarlo went to visit his
brother and woke up on the other side of the bars. Alexander had slipped some drugs into Giancarlo’s
drink, after which he fell asleep. Alexander then stripped down and got into his brother’s clothes,
and since they looked identical, once Alexander had walked out of the prison gates,
the guards didn’t believe Giancarlo when he told them what had happened.
As unbelievable as this sounds, Giancarlo wasn’t believed until he
complained enough to make the authorities take his fingerprints. After that, he was released,
although his brother managed to stay out of prison for another 13 months before he was recaptured.
The prison authorities of course were never certain that the brothers had planned all of this,
and Giancarlo wasn’t the victim he said he was. Still,
an investigation seemed to point to his innocence. That kind of thing has happened before. Notably,
one case involved a serial killer and one of the world’s most notorious scammers,
Charles Sobhraj, aka “the Bikini Killer,” or possibly known to you as “The Serpent.”
This psychopath fits the word “devilish” like a glove. His cunning knew no end, and he was always
prepared to ditch, sacrifice, or kill anyone close to him. To his credit, he was also arguably
the best prison escape artist of all time. One of those escapes involved his half-brother,
Andre. The two had been arrested in Greece, although Andre was basically
a petty criminal compared to his brother. When both were in jail for a small jewel robbery,
Charles convinced Andre to pretend to be him. Charles was a wanted man at this point in many
countries, and so if the authorities realized they had a very wanted criminal on their hands,
things could have gotten very bad for him. So, Charles told his brother, if you pretend to be
me and I pretend to be you, once they find out they have it wrong, I’ll be across the border,
and they’ll have no choice but to release you, seeing that you don’t have a criminal history.
They did this, but Charles managed to escape from a prison van after pulling one of his old tricks,
feigning an illness. That left Andre in prison with the authorities thinking he was Charles.
Andre told them that it was actually Charles that had escaped, which took a lot of convincing.
He served almost three years anyway, and Charles went on to do all sorts
of dastardly things in the years ahead. Now you need to watch “The Most Insane
Ways Men Escaped from Prison.” Or, have a look at “Dumb Prison Escape Attempts.”