Prisons have one job: to keep the most dangerous criminals locked away. And for the most part, locked away means no escape, right? But we all know of (and are even fascinated with) those stories that seldom occur when prisoners manage to make their way out of those escape-proof walls. But, while they may succeed at fleeing a prison, that doesn’t mean they’re in the green. Most, if not all, are eventually found and dragged back in.
And you would think that those who were brought back in would be put in conditions that would make future prison breaks impossible, right? Well, not so much. There are prisoners on this list (including a 19-year-old) who broke out not once, not twice, but multiple times. These escapes, which are often intricately crafted, prove that certain inmates, whether guilty or innocent, will do anything to be free.
These are the most insane, and impressive, prison escapes of all time, in chronological order.
1934: John Dillinger aka Public Enemy #1
Let’s begin with the man whose crimes earned him the notorious title of “Public Enemy #1” by the FBI. John Dillinger was a gangster, bank robber, and a murderer. He escaped prison twice. The first time was after being arrested in Tuscon, Arizona, in January 1934 on charges of killing a police officer during a bank robbery the year before.
He escaped from a jail in Ohio with the help of eight of his friends. After his capture, he was taken to Lake County Jail in Crown Point, Indiana – a prison that was considered “escape-proof.” But Dillinger proved them wrong. In what is now a famous tale, the gangster managed to escape with a fake gun.
Wood and Shoe Polish
On March 3, 1934, Dillinger and another inmate used a fake gun to break out of the facility. A true gangster, Dillinger used the sheriff’s brand-new V-8 Ford as his getaway car. To this day, there is still debate about exactly what the gun was made of, and how the escape actually happened. But most people believe that he used a wooden gun that he then painted black with shoe polish.
The prison guards, fooled by the gun and fearful of the gangster, allowed Dillinger to leave the prison. While on the run, Dillinger made the most of his “free time.” America’s “Public Enemy #1” went on a yearlong crime spree across the Midwest, robbing a dozen or so banks and police stations.
A National Spotlight
The boldness of his crimes, in which he took out ten men in the process, but the national spotlight on him as well as the hatred of every law enforcement officer in the country. “If I ever see John Dillinger, I’ll shoot him dead with my own pistol,” Crown Point Sheriff Lillian Holley said. “This is too ridiculous to talk about.”
In July 1934, a few months after his escape, he was shot dead by FBI agents during a shootout in Chicago. The infamous escape was dramatized in Michael Mann’s 2009 movie, “Public Enemies,” which was filmed in the actual jailhouse that Dillinger broke out of 75 years earlier.
A decade later, another infamous prison break occurred
1944: The Great WWII Escape
During the Second World War, thousands of prisoners of war were being held in the German-controlled Stalag Luft III camp. Little did the Germans know, some 600 prisoners were planning their escape routes. Thirty feet below the camp, the prisoners, were building three 2-foot-wide tunnels. The tunnels were named Tom, Dick, and Harry. The prisoners used tin cans and candles to scoop the soil, and they propped up the walls with bed boards.
It was on March 24, 1944, that the great escape began. Soon after it began, the first prisoner out of one of the three tunnels noticed that it wasn’t dug far enough. The tunnel’s exit only stretched as far as a few meters from the tree line, leaving them vulnerable to being seen. 76 men successfully fled before guards noticed the 77th attempted escapee. You can imagine how that ended…
1962: Escape From Alcatraz
The day three seasoned criminals escaped from Alcatraz Federal Penitentiary is the day that created one of the most famous jailbreak stories of all time, a story that Clint Eastwood decided to dramatize. On June 12, 1962, John Anglin, his brother Clarence, and Frank Morris placed handcrafted dummy heads in their beds to fool the prison guards and make their great escape.
Considering that Alcatraz was a maximum-security federal prison that was even located on an island off the coast of San Francisco, escapes were deemed impossible. But the three inmates managed to dig a tunnel through a concrete wall using just a spoon. They slipped through the vents in their cells and climbed up to the prison’s roof. They then slid down the pipes and used a makeshift raft made from over 50 stolen raincoats.
A Mystery To This Day
Their escape wasn’t noticed by the guards until the next morning. At that time, a full-on search began. The men were never heard from again, and no one knows if any of them even survived the escape at all. The FBI and Alcatraz officials assume, to this day, that they drowned in the water. What exactly happened that night remains a mystery even to this day.
There was speculation that the men moved to Brazil. A letter was submitted to the authorities in 2013, claiming to be from John Anglin. The letter stated that he was the only remaining one still alive at 83. Fingerprint and DNA evidence was inconclusive. However, a 2016 photo was revealed that apparently showed the two brothers in Brazil 13 years after their escape. The authorities have yet to confirm the photo’s (and the letter’s) authenticity.
1971: Frank Abagnale Jr., a Master Imposter
It’s no surprise that these stories get made into movies. Another now-turned-Hollywood-classic is the story of Frank Abagnale Jr., the notorious fraudster and imposter. Anyone who saw “Catch Me If You Can’ knows more or less the story of Frank and the chase after him. But the story of Frank’s escape from prison wasn’t in the movie.
So, to give you the gist, the con man was so good at evading the American federal government that he was later hired as a consultant to the FBI. Frank had learned the tricks of the trade from an early age. He started committing crimes at 15 and escaped prison twice. The first time was when he dodged deportation to the United States.
His Second, More Grandiose Escape
He managed to successfully escape from a British airplane as it landed at a New York City airport. He literally hopped the fence, took a train to Canada, and made a run for it. But he was eventually caught when he tried to flee to Brazil. He was recaptured in April 1971, after which he made his more grandiose escape.
While in federal custody, Frank, with the incredible skills he had, took advantage of a paperwork mix-up. When checking into the prison, the officer forgot Frank’s detention commitment papers. Frank seized the opportunity and convinced the prison guards that he was actually an undercover prison inspector. It took him weeks to build up the story, but amazingly, it worked.
An Instant Sensation
He told the guards that he had to meet with an FBI officer, who was parked just off of the prison grounds. The guards were giving him special treatment since they thought that they were helping the prison pass an inspection test. Eventually, Frank literally walked right out the prison, and the guards allowed it. The “FBI officer” parked outside? It was a friend of Frank’s who then took Frank straight to a bus to Washington, D.C.
Frank was on the run for another two months before being discovered and re-arrested. However, the prison’s PR damage was done, and the story got out. Frank quickly made headline news, and in time, he became an instant sensation for his ingenious escape.
1977: Ted Bundy aka The Campus Killer
It’s not my fault that all these stories became famous on-screen tales. But here’s another one: serial killer Ted Bundy, who escaped not once, but twice. The first time came during his trial in 1977 when Bundy was representing himself, and therefore he wasn’t shackled or even restrained. During a visit to the courthouse’s law library, Bundy broke free by jumping out of the second-floor window.
Six days later, he was found by the police. Later that year, Bundy suspiciously lost 20 to 25 pounds. He cut an opening in the ceiling of his prison cell and crawled his way out and through the duct system. Bundy was caught, though, and arrested again in Florida. But it was after he managed to take the lives of three more victims.
1986: Michel Vaujour (and His Wife) aka The French Bonnie and Clyde
This story wasn’t made into a Hollywood film… yet. But the tale might as well have been ripped right out of an action-adventure movie. In 1986, Michel Vaujour, who was serving a long prison sentence, found his way onto the prison’s roof, using nectarines that were painted to look like grenades. That’s right – nectarines. The story gets even weirder – and more Hollywood-esque.
On the roof of the prison, Vaujour’s wife, Nadine, was waiting for him in a helicopter. She flew away with her husband aboard, which would be ever so romantic if it wasn’t part of a prison break. The two then landed in a football field and exchanged the helicopter for a more practical getaway car. The French Bonnie and Clyde were later discovered in France. Nadine was arrested, and Michel was shot (but survived) after a failed robbery attempt.
1987: Richard Lee McNair aka The Escape Artist
Richard Lee McNair was no rookie. The former Air Force sergeant robbed a grain facility… only to get caught and sent to jail. He then made his first attempt to escape prison involved using lip balm to free himself from handcuffs. In his second attempt came when he crawled through a ventilation duct, but he was caught within hours. His third attempt, however, was truly legendary.
While working in prison, McNair crawled into a mailbag, and with his own breathing tube, he literally shipped himself out of prison. At some point, he slipped out of the package and entered the free world. Amazingly, he was stopped by a police officer and convinced the cop that he was a jogger. He was found, though, a year later.
1990: Tunnel Vision
In Santiago, Chile, 49 “leftist guerrillas” from the Manuel Rodríguez Patriotic Front tunneled their way out of prison. And this wasn’t just any old tunnel: their escape route took the men months to make, and it involved “lighting, ventilation, and carts on runners to remove the earth.” The route also went a full 80 yards – from the prison grounds all the way to an abandoned train station.
Among the 49 escapees were seven prisoners who had been accused of an assassination attempt of Chile’s military leader. Only seven of the guerillas were found and recaptured, including one who, unfortunately for him, got stuck in the opening at the end of the tunnel. Maybe he ate too many prison buns.
1992: Escape From “Hotel Escobar”
Yes, he is one of the most famous drug lords known to man. But instead of milking even more out of the already-exhausted story of the man who earned the title the King of Cocaine, let me just talk about his prison escape for a moment (because the list wouldn’t be complete without it). After negotiating with Colombian authorities, Escobar landed a pretty incredible deal… considering.
He agreed to be “imprisoned” on the condition that he could design and hire his staff to his liking. Handpicked guards, a soccer field, a dance club, and a chapel all led to the “prison” being referred to as “Hotel Escobar.” Once the police learned that Escobar was still running his empire from “prison,” they planned to transfer him to a conventional prison, but Escobar fled. He managed to avoid the police for 16 months.
1998: Jay “Junior” Sigler (and His Mom)
The bond between a mother and her son can be hard to break. Even a prison fence didn’t come between these two. In 1998, Sigler escaped prison when his mother, Sandra Sigler, and her boyfriend rammed a big-rig truck through not one but four prison security fences. Sigler and a fellow inmate, Christopher Michelson, jumped through the fences and into the truck.
The two convicts were caught the next day, however, after they crashed into another car, killing a 55-year-old man named Dennis Palmer. The two were given life sentences as a result of their ultimately deadly escape. Sigler and Michelson were captured 40 miles from the prison they broke out from.
2000: The Texas Seven
The biggest prison break in Texas history happened in December 2000 when seven inmates escaped from the maximum-security prison John B. Connally Unit in Kenedy. The team of seven was led by then-30-year-old George Rivas, who was serving 18 consecutive life sentences for kidnapping and burglary. The seven inmates (including two convicted murderers) overpowered two guards as well as eight maintenance shop employees.
They stole their uniforms and keys to a truck and locked them all in a utility closet. With stolen clothing, credit cards, and IDs, they impersonated civilians at the back gate of the prison. Four of them stayed behind to make phone calls to the tower guards, distracting them. The rest of the group raided the guard tower, stole weapons, and a maintenance pick-up truck. Then all seven drove away from the prison.
The Aftermath
But before leaving, they left a note for the police: “You haven’t heard the last of us yet.” And they were right. The Texas Seven, as they came to be known, went on a crime spree from San Antonio to Dallas and into Colorado. They were eventually captured, but that’s not before they killed 29-year old police officer Aubrey Hawkins in Irving, Texas.
They also robbed a Radio Shack and a sporting goods store and hid in a Colorado trailer park posing as missionaries. Once they were found, one of the seven took his own life. The other six, however, were taken back to the John B. Connally Unit. They were all sentenced to death. Three have been executed, and three are still on death row.
2001: El Chapo’s First of Two Escapes
The first time the Mexican drug kingpin escaped prison, all it took was a bribe and a couple of minutes of hiding in a laundry basket. The second time, which occurred 13 years later, wasn’t as simple. El Chapo was arrested in 2014, and 17 months later, he escaped again. This time via a mile-long tunnel system which led to a construction site. The tunnel he used was elaborate, with lights, air ducts, and even a motorcycle.
Once out, he gained a lot of media attention. A manhunt ensued, leading to a shootout and his recapture in 2016. He was sent to the United States, and by 2019, he was sentenced to life imprisonment in the United States’ most high-security prison. In January 2020, three high-profile Mexico City inmates, with ties to El Chapo, escaped. Reports said, “there had clearly been collusion with the prison staff.”
2001: Pascal Payet’s First of Three Escapes
What is it about French inmates and prison breaks with helicopters? Pascal Payet, a convicted French murderer and robber, broke out of prison in 2001. Like fellow French convict Michel Vajour, Payet made his way to the prison roof and got picked up by his friends in a hijacked helicopter. But Payet actually has three successful prison escapes under his belt.
It might be why he became internationally renowned. Two years later, he returned to the same prison, but this time to help three other convicts escape via helicopter. Payet was later caught but managed to escape, yet again, during a Bastille Day celebration. This time around, four masked men hijacked another helicopter.
Helicopters are His Vehicle of Choice
Payet was captured and transferred to a prison in an undisclosed location. In 2005 he was given a sentence of up to 30 years for the murder of a guard which occurred during a car hijacking back in 1997. He was in jail for a short time before he decided to – you guessed it – escape again. In July 2007, Payet arranged for his friends to hijack – you guessed it – a helicopter.
They took the pilot hostage and forced him to fly to the prison where Payet was being held. And when they reached the place, Payet was there waiting for them on the roof. While his third escape was also successful, it was nonetheless his last. He was eventually recaptured in Spain and has been in prison ever since. But I’m sure he’s planning another helicopter breakout.
2008: Sarah Jo Pender and Her Prison Guard Lover
Yes, there is a woman on this list. In 2007, convicted murderer Sarah Jo Pender exhausted all of her appeals and needed to get creative if she was ever going to see the light of day again. She would later say: “I had no hope left, and I chose to create my own justice. I served the equivalent of 21 years of my sentence, and I felt that was enough. I escaped because I felt justified in doing so.”
Okay, so how did she do it? Well, it started by getting involved with a prison guard. In 2008, she hid in the backseat of his car, and he drove off of the prison grounds. She then went into the car of her former cellmate, who took her to Chicago, where she hid out. But once her neighbor recognized her from a rerun of the show America’s Most Wanted, she was ratted out and recaptured.
2012: Ronaldo Silva’s Escape in Drag
Ronaldo Silva was sent to a prison in Brazil on a drug trafficking charge, and in 2012, he escaped. How? Well, it involved dressing in drag. In preparation for his big break, Silva shaved his arms and legs, and even put on fake nails. He told his wife, who came for weekly visits, to bring an extra outfit next time, along with a wig, high heels, and red lipstick.
When his wife came for her next visit, she gave him her the clothes she was wearing that day and changed into a spare outfit she brought with her in her purse. That’s when a newly-feminine Silva literally walked out the front door of the prison, right past the guards and out onto the street.
Dude Looks like a Lady
Silva walked right out without attracting any attention from the prison guards or any other inmates. But, as he walked towards his friends who were waiting for him at a bus stop, a clever police officer noticed something strange – something that couldn’t be missed so easily. He saw Silva struggling to walk in the high heels.
The cop also spotted that something wasn’t quite right. Silva’s freedom was short-lived. Apparently, Silva didn’t spend any of his preparation time practicing his walk in high heels. Within 30 minutes of his prison break, the police noticed a woman “walking funny” on the street, and they connected the dots. As for Silva’s wife, she claimed that while she did bring him the clothes, she had no idea what he intended to do with them.
2012: Choi Gap-Bok aka The Korean Houdini
There are loads of benefits to practicing yoga, but escaping prison isn’t one of the first things that come to mind. After practicing yoga for 23 years, Choi Gap-Bok was arrested for robbery in South Korea. One night, five days after his arrest, when the prison guards were asleep, the 5’4” man used his yoga expertise to get himself out.
He lathered himself in body lotion and used his yoga moves to slip himself out of a food slot! That slot was 5.9 inches tall and 17.7 inches wide, by the way. The entire process took him a mere 34 seconds. It took the police, however, six days to locate him.
Next is another escape from the year 2012…
2012: Zetas Drug Gang Escape
In 2012, one of the deadliest prison riots in Mexican history occurred. Members of Mexico’s Zetas drug gang were serving time in the Apodaca prison. They started an incredibly violent riot against other prisoners from a rival gang (the Gulf cartel). Zetas gang members stormed the cells of the Gulf members as they were sleeping.
By the time the violence was over, 44 Gulf cartel men were killed, and 12 were injured. But those aren’t the ones who escaped. 37 non-gang related prisoners took advantage of the chaos and escaped while guards were distracted with the riot. 21 prison officials ended up getting charged with involvement in the deadly riots. 24 of the 37 who escaped were either killed or re-arrested.
2014: TJ Lane’s Nine Hours of Freedom
In 2014, 19-year-old TJ Lane, who was sentenced in 2012 to three life sentences for a school shooting, broke out of prison. Lane, along with another convicted murderer, Lindsey Bruce, and a convicted kidnapper, Clifford Opperud, broke out of the medium-security Allen Correctional Institute in Ohio. The three stooges used a homemade ladder to climb the prison walls.
The inmates went through a crawlspace to a padlocked warehouse next to the recreation yard, where they spent months making a ladder from whatever materials they could find. On the night of September 9, 2014, the three convicts used the 13-foot makeshift ladder to climb to the top of the building and then jumped 15 feet over the prison walls. All three were captured within nine hours of their escape.
2014: Nini Johana Úsuga David – The Drug Lord’s Sister
Here’s another woman on this male-dominated list. Nini Johana Úsuga David, the sister of one of the biggest drug lords in Colombia, managed to escape prison by walking out the front door (which apparently is easier than I imagined). Nini’s 2014 escape was so well-planned that she didn’t even need to hide.
Nini, known as “La Negra,” had been arrested for her work in the deadly Los Urabeños gang. She was released from prison and walked right out the front doors after showing her “release papers.” But, unfortunately for the police, those papers were falsified and forged. This high-profile escape led Colombian President Juan Manuel Santos to fire the prison director. It is pretty embarrassing…
2015: Richard Matt and David Sweat’s Elaborate Maze
At 5:30 a.m. on June 6, 2015, prison guards at the Clinton Correctional Facility were busy doing their morning cell checks when they noticed something wrong. Two convicted murderers, Richard Matt and David Sweat, weren’t in their beds. That’s when one New York State’s largest manhunts began. Sweat and Matt spent months planning their break.
Both inmates were working in the “privileged” sections of the prison, including the kitchen, where they had access to tools. When they would walk around the prison field, the two men realized that a bump in the field was actually a pipe – a pipe they could crawl through. Matt established a relationship with the prison tailor, a woman named Joyce Mitchell, which came in handy…
Have a Nice Day
Richard Matt convinced the tailor to sneak in hacksaw blades in frozen hamburger meat. The two inmates then used the blades to cut holes into their cells, digging their way through an elaborate maze of pipes throughout the prison’s walls. The duo crawled through a steam pipe that they were able to slice open, and made their way through a manhole to get above the ground.
The men even left dummies with their prison sweaters in their beds to fool the guards during their nightly check. Reportedly, they left a note: “Have a nice day.” Originally, the plan was to have Joyce meet them outside and further help them with a getaway vehicle. But, Joyce failed to show up, and the pair had to make it on their own.
Three Weeks and $23 Million Later
Three weeks and $23 million later, Matt and Sweat were found, but only Sweat was taken into custody alive. After several days on the run, the two men were located, and after a shootout, Sweat was wounded and captured, but Matt was shot dead. “The married 51-year-old Joyce Mitchell said that she “enjoyed the attention, the feeling both of them gave me.”
But it was Matt that she had a physical relationship with. Mitchell pleaded guilty to her involvement in their escape and was sentenced to 7 years in prison. She is still serving her time at Bedford Hills Correctional Facility for women. So far, she’s been denied parole twice. I guess love comes at a price.
2017: The Alabama Twelve
In July 2017, twelve inmates escaped from a jail in Jasper, Alabama. They smeared peanut butter over a door’s sign, which indicated that the door led to the outside. So, as simple as it was when the inmates asked the guard to open the door for them, the guard thought he was opening a cell door and not an exit door.
The escapees then ran for it and jumped the fence using prison blankets. Ten out of the twelve prisoners were captured within 12 hours. The last one, Brady Andrew Kilpatrick, was found a few days later in Florida. Police were offering a $500 reward for any information leading to the arrest of any of the remaining escapees.
2018: Redoine Faid – Explosives and Helicopters
The French gangster was 25-years for a failed robbery in 2010 that killed a policewoman. On April 12, 2013, he broke out of prison… for the first time. The escape involved explosives to blast through five prison doors, letting him break free. But he had to use hostages during his escape. Within a few weeks, he was arrested in France, as he was making plans to escape to Israel.
Five years later, on July 1, 2018, Faid made his second escape. This time, he did it French gangster style, with helicopters, of course. Three masked men hijacked a helicopter, pretending to be flight students, and forced the pilot to land in the prison’s courtyard.
France’s Most Wanted Criminal
The criminals then landed the helicopter and left the pilot unharmed, moving on to take their first getaway car. The plan was elaborate and involved more than one vehicle. Soon after their first getaway ride, they parked the car in a shopping mall and set the car on fire. Yes, this is basically a scene from an action movie.
After setting that car on fire, the men continued their escape in a white van (of course). Meanwhile, the police found the abandoned helicopter, but they didn’t find Faid yet. The gangster quickly, and understandably, became France’s most wanted criminal. Three months after his impressive escape, however, he was caught by the police.
2020: 75 of Paraguay’s Most Dangerous Criminals
The most recent prison escape was referred to as “the biggest prison break from our facilities” by Paraguay’s justice minister. In January of 2020, at the peak of the Coronavirus outbreak and early on a Sunday morning, 75 prisoners escaped prison in Paraguay via an underground tunnel. Forty of them were from the Brazilian drug cartel Primeiro Comando da Capital (or PCC).
At the time of the escape, the authorities stated that it was “clear” that the prisoners were aided by the prison guards. In fact, the inmates dug their tunnel so openly that some officials believe that it was even a trick to take the responsibility off of the guards. At least five guards were suspended. So far, only 11 of the escapees have been recaptured.
Brian Bo Larsen Holds the Record
Brian Bo Larsen may just hold the record for the most prison escapes of all time. In total, the Danish criminal managed to escape prison a whopping 22 times. His methods ranged from using saws to break through window bars to hiding in trash cans before being taken off the prison grounds. But Larsen’s most elaborate scheme was the escape that involved using a bulldozer that was left on prison grounds.
Larsen drove the bulldozer right through the walls of the prison, freeing himself as well as 13 others. But while Larsen might be a pro at getting himself out of jail, he doesn’t seem to be so successful at keeping himself out. In one instance, he was caught stealing a car.
One of the Best Escape Artists
Larsen is simultaneously one of the worst criminals and the best escape artists in Denmark. Now in his forties, he has spent the majority of his life in and out of the prison system for crimes ranging from theft to armed robbery. It might be obvious that the prisons in Denmark are a little different from those in America.
The prisoners get comfortable cells, wear their own clothes, and even eat with their families once a week! There also aren’t any high walls, barbed wire, or shower stabbings. But despite the comfy prison life in Denmark, Larsen chose to escape all but 22 times. One of Larsen’s biggest downfalls, among the constant crimes, is his inability to stay out of prison.