Top 10 Greatest Prison Escapes Of All Time


Prison escapes are something that have fascinated the public for thousands of years. It would seem to make all the sense in the world that a prisoner would dedicate all

of their time to plotting their escape. After all, what else have they got to do?

Another misconception is that criminals are dumb. Many criminals are actually quite smart — except for that one time they slipped up and got caught. But these criminals are the ones that need to have an extra eye kept on them. Even with today’s modern security measures, prisoners are still making headlines all time for their escapes. Here are the greatest prison escapes of all time.


10. David Sweat and Richard Matt

David Sweat and Richard Matt Top 10 Greatest Prison Escapes Of All Time

In 2015, David Sweat and Richard Matt had all of America’s attention when they escaped from a correctional facility in Upstate New York, causing a nationwide manhunt. They managed to escape with the assistance of a prison worker, of whom they’d gained her trust. Matt was killed in the manhunt, Sweat was apprehended and has just been indicted on two counts of escape in the third degree. The accomplice who helped them escape will be spending the rest of her life in jail — unless she escapes, that is. 

9. John Dillinger

John Dillinger

John Dillinger’s gang killed ten people while robbing more than a dozen banks in the 1930s. When he was finally apprehended, it drew the attention of the entire U.S. So the nation became even more fixated on the story when he escaped from prison. Using a fake gun he had carved from wood and painted black with shoe polish, he forced his way out of the prison and made his escape. Less than a year later, he was shot dead by FBI agents. 

8. The Texas 7

The Texas 7

Seven inmates in the John B. Connally Unit maximum-security prison managed to escape in December of 2000 in what was Texas’s biggest prison break in their history. Two convicted murderers and five other men, including leader George Rivas, forced their way past two guards and several members of the maintenance crew. Like something out of a Terminator movie, they stole their clothes and keys and fled to freedom. One committed suicide. The others were captured and three of them have been executed. 

7. T.J. Lane

T.J. Lane

What makes this prison escape so astonishing is that the perpetrator was only 19 years old at the time. T.J. Lane killed three classmates in a school shooting in 2012. Using a homemade ladder to climb over the medium-security prison’s walls, Lane escaped in September of 2014. Luckily for the families of Lane’s victims, he was quickly apprehended again. 

6. Frank Abagnale

Frank Abagnale

You can be sure you were responsible for one of the greatest prison escapes of all time when Steven Spielberg makes a movie about it. Frank Abagnale, escaped prison in 1971 after he convinced guards he was a prison inspector. He was able to remain on the loose for two months before being recaptured in Washington, D.C. 

5. Alfred Hinds

Alfred Hinds

Alfred Hinds, or “Alfie,” as he was known, was a truly great escape artist. You know you’ve committed a successful prison escape when you’re able to get away with it legally after the fact! After being charged with robbery, he was sentenced to 12 years in prison. He managed to escape three times, later getting pardoned by the British government on a technicality. Not bad! 

4. Joaquin “El Chapo” Guzman


Known as the world’s most powerful drugs lord, El Chapo has an estimated worth of $1 billion, according to Forbes. He succeeded Al Capone as holding the title of Chicago’s Public Enemy Number 1 by The Chicago Police Commission. His Mexican drug cartel is responsible for smuggling more drugs into the U.S. than any other in history. He was arrested in Guatemala in 1993 and escaped prison in 2001 by hiding in a laundry cart. In 2014, he was found by authorities, but he escaped prison again in July of 2015. Now, Mexico’s government says they’ve got him again. But is it only a matter of time before he’s back on the loose? 

3. Hugo Grotius

Hugo Grotius

Of all the greatest prison escapes in history, this may be the one that started it all. The earliest known prison escape was by writer and politician Hugo Grotius in the Netherlands in 1621. During a broken war truce, authorities thought he was stirring up too much trouble, so they locked him up in a cell, where Grotius published essays that continued to stir the pot. Grotius managed to stow away in a storage container, and his story became famously known as the first prison escape. 

2. Leon Feldhendler and Alexander Pechersky

Leon Feldhendler and Alexander Pechersky

Here’s a prison escape we can actually get behind: during the Holocaust, Leon Feldhendler and Alexander Pechersky were prisoners at the Sobibor Death Camp. Together, these men organized one of the most successful prison escapes of all time. They made knives and shanks out of whatever they could find around them and waiting until the time was right before striking the prison guards. The men led a very successful revolt, freeing more than half of the 300 Jewish prisoners in the camp. 

1. Frank Morris and Clarence and John Anglin

Frank Morris and Clarence and John Anglin

Clint Eastwood starred in the movie depicting the true story of what is perhaps the most infamous prison escape of all time. If you’re going to prison and plan on trying to break out, Alcatraz would probably be your very last choice of residence. But Alcatraz naturally housed the smartest and most dangerous criminals, and for Frank Morris and Clarance and John Anglin, that was certainly the case. Able to forge weapons out of the objects around them, the three escaped from the building through a ventilation shaft. They made a raft and successfully fled to the San Franciso Bay, making this top the greatest prison escapes of all time.

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