If you behave yourself in life and aren’t maliciously framed for a crime you didn’t commit by your evil twin, you will probably be able to stay out of prison. That’s a good thing because those places are terrible for prisoners. Obviously, that’s by design. Unless you’re a Martha Stewart-type and sent to a place like “Camp Cupcake,” the whole idea is to make your time there miserable so you’ll change your wicked ways once you get out and never, ever want to go back.
If you behave yourself in life and aren’t maliciously framed for a crime you didn’t commit by your evil twin, you will probably be able to stay out of prison. That’s a good thing because those places are terrible for prisoners. Obviously, that’s by design. Unless you’re a Martha Stewart-type and sent to a place like “Camp Cupcake,” the whole idea is to make your time there miserable so you’ll change your wicked ways once you get out and never, ever want to go back.
But the fact that it’s so bad on the inside means some people aren’t willing to wait to be legally released to get the heck out of there. It’s not a decision inmates make lightly. Trying to escape is extremely dangerous (guards do have guns after all), and most of the time they fail. There are some prisoners, though, who not only manage to break out but successfully stay out.
William Maxwell owed his wife his life, literally
The Tower of London is like the British Alcatraz: ridiculously hard to escape from. Only a couple people have managed it in about a thousand years. Perhaps no escape was more audacious than William Maxwell, the Fifth Earl of Nithsdale’s in 1715. And he managed it because he had a very intelligent, very sneaky wife.
According to the Scotsman , Maxwell got in trouble when he picked the wrong side of a rebellion that was trying to overthrow King George I. He was arrested and convicted of treason, which meant he was going to lose his head. His wife, Winifred, went to the king and begged him to spare her husband, but to no avail. Time was running out; it was the day before his execution and he had even already written a speech to give moments before losing his hat-holder.
But Winifred had a plan. She often visited him with two of her maids. On this last visit, one of the maids switched clothes with Maxwell. He then simply walked out of his cell with his wife, holding a handkerchief to his face and pretending to be crying because it would have given the game away pretty quickly if the guards had noticed his beard. Winifred then came back again later and somehow managed to leave with her maid.
The earl knew better than to stick around. He and his awesome wife fled to Rome and he lived there until he died 33 years later.
Vassilis Paleokostas has a flare for the dramatic
Ever wished for a modern-day Robin Hood? A Greek one, by chance? You’re in luck, you hyper-specific wisher. Meet Vassilis Paleokostas. According to the BBC , over three decades he has taken huge amounts of money from state-owned banks, plus kidnapped wealthy industrialists and ransomed them. Then he gives a lot of that money to the poor. He’s also unlike other criminals in that he claims never to have harmed anyone. But he’s still a crook, and a wanted man.
What started out as petty theft soon escalated into complex schemes and taunting police. Despite being called “uncatchable,” Paleokostas has been to prison a few times — he’s just really good at getting out. The first time he got banged up because he had tried to drive a stolen tank through the wall of a jail to rescue his brother. Eight months later he was out, after using bedsheets to climb over the wall. But that was just the beginning.
Paleokostas was caught the second time after he was injured in a car accident. He was in jail for six years before his brother returned the old favor by hijacking a helicopter and coming to get Paleokostas. He was on the run two years that time before he was arrested again. This time he didn’t even make it to trial. The helicopter thing had worked once, why not twice? Lo and behold, a hijacked chopper came for him and he escaped a final time in 2009.
Frederick Mors was the smart kind of crazy
Old people die, that’s just to be expected. But even nursing homes start to notice when an inordinate number of their patients die in a very short period of time. That’s what happened in the German Odd Fellow’s Home in New York during 1914 and 1915. Even though the authorities thought something might be up, there wasn’t really anything they could do, until a guy wearing actual lederhosen and a jaunty hat with a feather in it walked into the Criminal Courts building and asked to speak to a lawyer.
According to The Mammoth Book of Bizarre Crimes , that man was Fredrick Mors, an Austrian immigrant. He admitted he had killed eight people at the old folks home, where he worked as a nursing assistant. He said he had perfected a way to end someone’s life using chloroform and that he did it to end their suffering. (There is some evidence he may have been told to get rid of troublesome patients.) He was found to be crazy and sentenced to a prison for the criminally insane.
Mors may have been nuts, but he wasn’t stupid. He wasn’t going to stay locked up in a loony bin forever. By the 1920s he had figured out a way to escape. History doesn’t record exactly what he did, but whatever it was, it worked. He got out of there and went on the run, managing to avoid recapture. Hopefully he had all the murdering out of his system by then.
John Patrick Hannan is the world’s best at not getting caught
You’d understand why some prisoners would go through all the effort and danger of trying to escape. It can’t be fun facing the prospect of decades or even life behind bars. But John Patrick Hannan didn’t even want to spend two years there.
Hannan was sentenced to 21 months inside in 1955 after he stole a car and assaulted two police officers, according to the Telegraph . But before the year was out, he and another inmate, Gwynant Thomas, made their escape. They climbed over the prison walls using the biggest cliche ever: knotted sheets. Then they broke into a gas station to steal overcoats (presumably to hide their uniforms) and those staples of freedom, beer and cigarettes.
Thomas was rearrested within 16 hours, but Hannan kept running. In fact, he was so successful that he holds the world record for longest escape from custody, passing 60 years in 2015. If he is still alive he is now over 80 and probably living in Ireland.
It’s not that the police didn’t try to find him. Right after the escape they set up roadblocks and used tracker dogs. And they kept up the search until 20 years ago. By the end their efforts seemed a bit half-hearted, like when they put a message in the police newspaper saying, “If you read this Mr. Hannan please write in, we’d love to hear from you.” Shockingly, the world’s most successful fugitive wasn’t immediately convinced to give himself up.
Glen Stark Chambers had the brains to succeed
Glen Stark Chambers was a piece of work. In 1975 he beat his girlfriend to death and was put on death row, but his sentence was commuted to life a year later. Just after he was convicted he managed to escape but was recaptured. Law enforcement wouldn’t be as lucky the second time.
Chambers was placed in a maximum-security prison in Florida, but he behaved himself and got special privileges. This included participating in a program where inmates built furniture. One day in 1990 he was helping load that furniture onto a truck and decided to go for it. He hid himself in the truck’s cab and the driver drove away with no idea he had a passenger. Chambers hopped out during a traffic jam and that was the last anyone ever saw of him, other than some possible sightings in the early days.
The day Chambers escaped, the prison supervisor said, “He’ll turn up eventually. They all come back.” Almost 30 years later, he might be eating his words. Not that the hunt isn’t still on. As of 2013, the Florida Department of Law Enforcement was actively looking for him. Brannon Sheely, the special agent in charge of Chamber’s case, was almost stupidly optimistic, saying: “I really feel like this is going to be a success story. We are going to locate him.” While he admitted Chambers’ genius-level intelligence might make that difficult, he obviously lives in hope. Maybe one day they’ll get their man. (Probably not.)
Glen Stewart Godwin had friends in low places
Escaping once is hard enough. The key once you’re in the wind is to not get arrested again on completely different charges. But that didn’t bother Glen Stewart Godwin, because he was really good at breaking out of prison.
CBS Sacramento says Godwin was originally put inside for murder in 1987. He didn’t stay there long, but he had a lot of assistance. His cellmate was about to be released on parole, and they made an agreement that he would come back and help Godwin get out. In a very Shawshank -esque plan, it was decided he would go down a storm drain and out to freedom. His buddy helpfully sawed the bars blocking the drain, left a flashlight, then spray-painted arrows and happy faces showing him the way to go.
Once Godwin escaped, he hopped in an inflatable boat (also left by his friend) and met up with his wife. Then they both fled to Mexico. He could have lived the high life there, if he hadn’t literally wanted to get high. Only five months after arriving, he was arrested on drug charges and sent to a maximum-security prison. It didn’t matter to him that much, though — he escaped again. In 1996 he was added to the
FBI’s Most Wanted list.
It didn’t work out so well for his accomplices. Both his cellmate and his wife were arrested for their parts in helping Godwin escape. Meanwhile he enjoys sweet freedom south of the border.
George Edward Wright’s crimes kept escalating
If you’ve managed to escape prison once, you’d think the logical thing would be to count your blessings and lay low after that. George Edward Wright did not get that memo.
His crime was supposed to be small, according to GQ . He and a friend tried to rob a gas station. But when the attendant wouldn’t give up the money, they beat him and then his partner shot him. The man died two days later.
Wright pleaded no contest and was sent to a maximum-security prison, where he considered trying to escape. But he wouldn’t get his chance until years later when he was transferred to a much more relaxed place. There he was approached by two guys who asked him if he wanted to try busting out with them. Wright was in on getting out. One night they walked off after an inmate count and hid in a cornfield. An hour later the alarm was raised, and the warden discovered something embarrassing: his car was missing. The felons had hotwired it and driven away.
On the outside, Wright lived with two other guys on the run and somehow they decided they would flee to Algeria. Only their way of getting there was seriously flawed: They hijacked a plane. They managed to get away with it without getting shot, and eventually Wright ended up in Portugal. And the FBI believes he’s still there today, but Algeria refuses to extradite him so he remains a free man.
Jerry Bergevin wasn’t really interested in teeth
According to Jerry Bergevin’s granddaughter, Angela Michels, who has been researching his life , he and his wife were the Bonnie and Clyde of the 1950s. (That’s maybe a bit much. He was definitely a repeat criminal, but his story isn’t on the same level.)
Michels says he was doing it for altruistic reasons. They were poor and had three kids to feed, so Bergevin became a pro safe cracker. He also just had a dislike of authority in general — once when a cop pulled him over and reached into the car to turn off the ignition, Bergevin drove away, taking him along for the ride.
Eventually his crimes caught up to him in 1962, when he was put on trial for breaking into a drugstore. He got 10 to 15 years but started hatching a plan to escape. Bergevin began writing letters asking to be sent to a less secure prison so he could participate in a dental technician training program. Even though his behavior behind bars was less than perfect, his transfer was eventually approved in 1969. This new prison had only a barbed wire fence around it.
Bergevin never started the dental program. Instead, he just went missing one day. This set off a 43-year manhunt, but in 2012 they finally gave up the search. He would have been 80 and hadn’t been heard from in so long that authorities declared him a free man.
Assata Shakur is enjoying the Caribbean life
Joanne Deborah Chesimard, who goes by Assata Shakur, joined the Black Liberation Army and the Black Panther Party in the 1970s. That put her on authorities’ radar. It was a conflict that would end in tragedy.
The Guardian says it went down like this. In 1973, Shakur and a friend were pulled over by two state troopers, ostensibly because they had a broken taillight. Whatever happened at that traffic stop, it went south really quickly. Within minutes her friend and one of the cops were shot dead, and the surviving cop and Shakur were both wounded. Four years later she was sentenced to life in prison for murder.
Shakur wasn’t in there long. In 1979, some other BLA members decided they would get her out by posing as visitors to the prison. Once, inside they captured two guards in charge of a prison van, according to one of the accomplices , then bundled Shakur into the van and drove off. Then they switched cars and put her up in a series of safe houses until it was decided she should leave the country.
She fled to Cuba, where she has lived for decades. Cuba has no extradition treaty with the U.S., so chances are she isn’t coming back anytime soon. Not that the government isn’t trying. Forty years after her original arrest she was added to the FBI’s Most Wanted Terrorist List, the first woman to get that “honor.”
The men who escaped The Rock
In 1962, brothers John and Clarence Anglin and Frank Morris did the unthinkable: They escaped from Alcatraz , what the FBI calls the “ultimate maximum-security prison.” It was supposed to be impossible. The 36 other prisoners who had tried it had all failed. But these guys might actually have made it.
They had an ingenious plan. They used crude homemade tools to loosen the air vents in their cells. These led on to an unguarded corridor. They set up a workshop where they spent months making paddles, and a raft and life vests out of old raincoats. They built dummy heads out of plaster and real hair, which fooled the guards the night they made their escape and sailed off into the Bay.
There has been an interesting, more recent development. The big question was always: Did these guys survive? The BBC reports that in 2018, the San Francisco police released a letter they had received in 2013, claiming to be from John Anglin. He said, “Yes we all made it that night, but barely!” Not only did they survive, John claims they all made it to old age, with his dying in 2008 and Morris in 2005. He even offered to turn himself in, so long as he was promised no more than one year in prison, and access to medical care since he said he had cancer. The cops turned the letter over to the FBI for handwriting analysis (it was deemed “inconclusive”
but didn’t take the fugitive up on his offer.
