The most audacious prison escapes of all time

Ronnie Biggs escaped from prison, July 8th 1965

On the 8th of August 1963, a man named Bruce Reynolds led a gang of 14 men on a mission to hold up a train carrying huge sums of money aboard. ‘The Great Train Robbery’ would go down as one of the most infamous crimes in British history.

£2.6 million was stolen - that’s the equivalent of well over £50 million today. It’s a fascinating crime, without a doubt, but we’re more interested in the exploits of the man who went on to become the most known of the gang - Mr. Ronnie Biggs.

The career criminal was arrested, tried and convicted along with nine of his colleagues. Unlike the others, he didn’t take his 30 year sentence lying down. Biggs took a much more standing up approach. Standing up and then shimmying up ladder to freedom, in fact.

It's 54 years since Ronnie Bigg’s gutsy escape, so we thought we’d cast our minds back to the event and also delve into a few other truly remarkable and daring prison breaks…

Train Robber Ronnie Biggs scales a 30ft wall

At around 3pm on July 8th 1965, prison guards in the yard noticed a head pop up at the outside of one of the prison walls. As they raised the alarm, the man threw a rope ladder over the 30ft wall. Ronnie Biggs and three other prisoners climbed up it, and lowered themselves into vehicles waiting outside. The guards were held back by other inmates, who were stopping them from intervening.

Biggs eventually fled to Brazil, via Brussels, Sydney, Melbourne and Panama. He knew he would caught be caught at any moment so used some of his new-found wealth to have cosmetic surgery in order to change his appearance. He lived a free man in Rio de Janeiro (due to Brazil not having an extradition treaty with the UK) until 2001 when he flew back home, voluntarily, to face the music. 

He was imprisoned until 2009 when he was released on ‘compassionate grounds’ just before his 80th birthday. He died just four years later in a care home. Weirdly enough, just hours before the first episode of a new BBC television drama series called The Great Train Robbery was due to start.

Leaving through the back door (covered in dirty underpants)

Drug lord Joaquín Archivaldo Guzmán Loera used to be the boss of the Sinaloa Cartel, the largest drug cartel in all of Mexico. Big in the world of cocaine and marijuana, but short in stature (‘El Chapo’ roughly translates as ‘Shorty’), the man never let his height stand in his way. In fact, he never let anything get in his way. Even prison. 

El Chapo made his first jail break, back in 2001, in a relatively modest and straightforward manner. As news hit that he was due to be indicted and tried in the USA, he moved quickly to grease prison guards’ palms and secret himself at the bottom of a laundry cart, making his way out of the prison in the truck that picks up dirty linen. Apparently Guzmán had to shell out $2.5m in bribes in order to do so.

Tunnelling out (El Chapo pt. 2)

For his second disappearing act, some 14 years later, El Chapo plotted his way out of the rather futuristically-named ‘Federal Social Readaptation Center No. 1’. How? Well, again, it required collusion. And a not inconsiderable amount of effort. 

He slipped out of his cell downwards, dropping down into a tunnel which had been purpose-built for his escape. 5ft7” tall (which was more than high enough...), the tunnel was a mile long and even had a motorbike in it for a speedier exit. Now that’s efficiency.

‘Hamburger saws’ used during an escape at Dannemora

The maximum-security prison at Dannemora is New York state’s biggest penitentiary. In 170 years no one had ever broken out. Until, in 2015, convicted murderers David Sweat and Richard Matt did just that.

Both men seduced a female employee who smuggled them hacksaw blades in some hamburger meat. Sweat then painstakingly cut a hole in the steel wall of his cell and another in a large metal pipe behind that wall. The men then crawled through a labyrinth of tunnels, eventually popping up outside the prison walls via a manhole. They went on the lam and were eventually tracked down and shot. Sweat survived and was rearrested, while Rich died.

Anyone interested in this story should check out Ben Stiller’s fantastic 7-part dramatisation of the incident starring Benicio del Toro, Paul Dano and Patricia Arquette. Made for Showtime, Escape at Dannemora aired last year and might well be the piece of best prison escape drama ever committed to celluloid. 

Using dummies to escape from Alcatraz

It’s just a shell of a place now, nothing more than a tourist attraction to the millions of visitors than San Francisco welcomes every year. But it wasn’t all that long ago that Alcatraz was the most feared and watertight prison in the United States. It was famous for being on an island, making escape all but impossible.

Well. Escape was possible. Survival, though? That was another matter. Frank Morris and John and Clarence Anglin managed to cut holes in the walls of their cells, and make it outside via a ventilation duct to a fence, which they then scaled. Once over they attempted to sail to the mainland in a raft made from old raincoats and cement. None of the men were ever seen or heard from again. It’s assumed they drowned.

The most memorable and unusual part of their escape was how they avoided the alarm being raised by their absence. Before leaving their cells, the men effectively replaced themselves with dummy versions that they had fashioned (comprising of paper-mâché heads and a blanket).

Sound familiar? Well, quite. Frank Morris’ incredible story was told by Don Siegel and Clint Eastwood in the gripping 1979 prison flick Escape from Alcatraz.

Nectarine grenades

As we’ve seen so far, good prison breaks are not solo efforts. You need co-conspirators. Michel Vaujour, an armed robber locked up in France in the eighties, knew this. He didn’t turn to his gang to bust him out of jail, though. He asked Nadine, his wife. Who was only too pleased to help.

She landed a helicopter - oh yes - onto the roof of the Parisian prison, picked up her husband and the pair flew off, making good their escape. All very dramatic so far, but it’s how Michel got to the roof alone that’s the most amazing, bizarre and amusing. He used the threat of setting off grenades. Except they weren’t grenades. You can’t get grenades in prison. You can get nectarines, though. And dark green paint.

Catch me if you can… again

Not all prison breaks require sawing through walls, tunnelling holes or threatening to chuck painted fruit. It’s possible - it seems - to just talk your way out. At least it was for Frank Abagnale, anyway. A smooth-talking fraudster and grifter, Abagnale was so adept at manipulation he managed to break out of prison before even getting there.

The marshall in charge of the prisoners had forgotten his papers. There was no record of who was aboard the bus carrying new prisoners when it pulled into the yard. Frank seized his opportunity and spun a web of lies to prison officials, claiming to be an undercover prison inspector who was posing as an inmate in order to test the procedures of the place. His plan worked and he walked on out of there.

Why Steven Spielberg didn’t incorporate that as a scene into his 2002 life of the man’s life, Catch Me If You Can, is anyone’s guess.