Prisons basically have one job: to keep the nation’s most dangerous criminals safely locked away behind its walls. But things do not always go as planned. These prison escapes, often intricately crafted, show that some inmates, guilty or innocent, will do just about anything to break free from prison and experience another chance at freedom — and we really mean anything.
1. Ronaldo Silva
Ronaldo Silva was dragged into Penedo prison in Brazil on a drug trafficking charge, and in 2012, he decided he would go into drag in his wild attempt to escape. In preparation for his big breakaway moment, Silva shaved his arms and legs. He told his wife to bring an extra outfit to her next prison visit, along with a wig, shoes, and bright red lipstick.
Silva’s wife delivered, and the couple somehow swapped clothing. Then, a newly-feminine Silva was able to walk right out the front door of the prison. But his freedom was short-lived. Apparently Silva was not practiced in the fine art of walking in heels. Just 30 minutes later, police noticed a woman “walking funny” on the street, and connected the dots.
2. Choi Gap-Bok
There are plenty of benefits to practicing yoga, but escaping prison is not usually the first thing that comes to mind. After he’d been practicing yoga for 23 years, in 2012, Choi Gap-Bok was arrested for robbery in Daegu, South Korea.
So one night when the prison guards went to sleep, the 5-foot 4-inch Choi somehow was able to lather himself in body lotion and used his graceful yoga moves to slip out of a food slot that was just 5.9 inches tall and 17.7 inches wide. The entire process took just 34 seconds, and it took six days for police to relocate him.
3. Antonio Ferrara
French bank robber and murderer Antonio Ferrara was serving time in a prison in Fresnes, France, just south of Paris, and had no intention whatsoever of serving out the entirety of his sentence. One day, associates of his came to break him out of jail, and they came with a bang.
Eighteen people, including Ferrara’s own lawyer, blew up the prison gates and began firing at prison guards. Ferrara was able to escape and evaded police for 4 months. During the trial after his prison escape, police were so worried about another plot that 90 officers were in the courthouse when the 17-year additional sentence was announced.
4. Michel Vaujour
It was a prison escape that seemed like it was ripped right from an action-adventure movie. In 1986, Michel Vaujour was serving a long prison sentence when he “forced his way onto the prison’s roof by wielding nectarines that were painted to look like grenades,” as the Chicago Tribune reported at the time. Then the story got crazier.
On the roof, Vaujour’s own wife was waiting behind the wheel of — wait for it — an actual helicopter. She then flew away with her husband, which would be romantic if it was not part of a prison break. The two landed in a field and switched to a more practical getaway car. He was later discovered in France and rearrested.
5. The Texas Seven
In 2000, seven men being held in a maximum-security prison for a slew of violent crimes were ready to pull off their well-planned plot. Together, they overpowered civilian maintenance shop employees, stealing guns and a vehicle. They left a note behind for police, which read: “You haven’t heard the last of us yet.” They were right.
Over the next year, the “Texas Seven,” as the media would call them, went on to rob a Radio Shack, ransack a sporting goods store, and kill a police officer. Then, they hid in a Colorado trailer park posing as none other than missionaries. Police were able to locate the men, and one took his own life to avoid rearrest. The remaining six survivors of the Texas Seven were all sentenced to death.
6. Zetas Drug Gang Prison Escape
It was one of the deadliest prison riots in Mexican history. In 2012, members of Mexico’s Zetas drug gang serving time in the Apodaca prison staged an incredibly violent riot against prisoners from a rival gang known as the Gulf cartel. Zetas members stormed the cell block of Gulf members as they slept.
By the time the violence subsided, 44 members of the Gulf cartel had been killed and another 12 were injured. Meanwhile, 37 prisoners took advantage of all of the mass chaos and managed to escape while guards were distracted. Later, 21 prison officials were charged with being involved in facilitating the deadly riots, and 24 of the 37 who escaped were either killed or rearrested.
7. Richard Matt and David Sweat
At 5:30 on the morning of June 6, 2015, prison guards at the Clinton Correctional Facility were conducting their morning cell checks when they noticed that something had gone horribly wrong. Two convicted murderers, Richard Matt and David Sweat, were not in bed. One of New York state’s largest manhunts ensued.
The two inmates had cut holes into their cells, making their way through an elaborate maze of pipes within the prison’s walls. Then, the pair crawled through a steam pipe that they had managed to slice open, and made their way above ground through a manhole. Three weeks and $23 million later, both men were found, with only Sweat taken into custody alive.
8. Ted Bundy
Serial killer Ted Bundy was able to escape jail not once, but twice. The first instance came during his trial in 1977: Bundy was representing himself, and so he was not shackled or restrained. During a trip to the courthouse’s law library, Bundy was able to break free by leaping from the library’s second floor window. Six days later, he was picked up by police.
Later that same year, Bundy had suspiciously lost 20 or 25 pounds — not due to a loss of appetite, but because of an appetite for freedom. He managed to cut an opening in the ceiling of his cell and crawled his smaller frame through the prison’s duct system. Bundy was arrested again in Florida, after he had already managed to murder three more victims.
9. Frank Abagnale Jr.
Frank Abagnale Jr. was so good at evading the federal government that he was later hired as an FBI consultant. The successful con artist was once able to evade deportation to the United States when he escaped from a British airplane as it taxied into a New York City airport. He hopped the airport’s fence, took a train to Canada, and was caught as he tried to flee to Brazil.
While in federal custody, Abagnale took advantage of a paperwork mix-up and convinced prison guards that he was an undercover prison inspector. Under this ruse, he told prison guards he had to meet with an FBI officer, who had parked just off of the prison grounds. That FBI officer was actually a friend of Abagnale’s, who took the con man straight to a bus to Washington D.C., where he was discovered by police.
10. Manuel Rodríguez Patriotic Front Prison Escape
In Santiago, Chile, in 1990, no less than 49 “leftist guerrillas” almost exclusively from the Manuel Rodríguez Patriotic Front tunneled their way out of a prison. And we are not just talking about any tunnel: this escape route took months to make, and included “lighting, ventilation, and carts on runners to remove the earth.”
The escape route led a full 80 yards from prison grounds all the way to an abandoned train station. Among the escapees were seven prisoners accused in an assassination attempt of Chile’s military leader. Only seven of those who escaped were recaptured at the time, including one who got stuck in the opening at the end of the tunnel.
11. Pablo Escobar
After negotiating with Colombian authorities, the infamous drug kingpin Pablo Escobar was able to land a pretty incredible deal. He agreed to be “imprisoned” in exchange for the ability to design and staff his personal prison to his liking. Those specifications came with handpicked guards, a soccer field, a dance club, and a chapel. For obvious reasons, the prison named “The Cathedral” was given the nickname “Hotel Escobar.”
To no one’s surprise, police soon learned that Escobar was continuing to run his empire from prison, despite the deal that had been struck. They had planned to transfer him to a more conventional prison, but Escobar had other plans. Some hostage taking and a shootout later, and Escobar fled. He evaded police for 16 long months.
12. Nini Johana Úsuga David
Sometimes prisoners escape through tunnels, other times they walk right out of the front door. In the case of Nini Johana Úsuga David, who was the sister of one of the biggest drug lords in Colombia, her 2014 escape was so well-planned that she did it in plain sight.
David, known as “La Negra,” was arrested for her work alongside the deadly Los Urabeños gang. She was later released from prison and able to walk right out the front doors after showing released papers. Unfortunately for police, her release papers were falsified and forged. Her escape led Colombian President Juan Manuel Santos to call for the resignation of the prison director responsible.
13. John Anglin, Clarence Anglin, and Frank Morris
The escape of three seasoned criminals from Alcatraz Federal Penitentiary is easily one of the most famous jailbreak stories of all time. On the night of June 12, 1962, John Anglin, his brother Clarence, and Frank Morris all put handcrafted dummy heads in their beds to evade prison guards and made their great escape.
The three slipped through the vents of their cells and manged to climb to the prison’s roof, shinny down a pipe, and took a homemade raft into the frigid waters of San Francisco Bay. Then, they were never heard from again. No one knows if any of the men actually survived their prison escape, and what exactly happened that night remains a mystery to this day.
14. Richard Lee McNair
Richard Lee McNair was no prison escape rookie. His first attempt to escape involved the use of lip balm to free himself from handcuffs. In his second attempt, he crawled through a ventilation duct, but was caught in a matter of hours. But his third attempt was truly legendary.
While working in the prison, McNair actually put himself into a mailbag, complete with his own breathing tube, and literally shipped himself out of prison. At one point, after he slipped out of the package into the free world, he was stopped by a police officer and actually managed to convince the officer that he was a jogger. He was not found until a year later.
15. El Chapo
The first time that the Mexican drug kingpin Joaquín Archivaldo Guzmán Loera, more commonly known as El Chapo, escaped prison, all it took was a bribe and a few minutes hiding in a laundry basket. The second time, escaping maximum security prison involved a nearly mile-long tunnel system.
The tunnel El Chapo used was stunning and elaborate, and included lights, air ducts, and even a motorcycle. It eventually led to a construction site. A manhunt ensued, eventually leading to a shootout and El Chapo’s capture in 2016. He was extradited to the United States and in 2019, he was sentenced to life imprisonment in the United States’ most high security prison.
16. Jay “Junior” Sigler
The bond between a mother and her son can be as hard to break through as a prison fence. And in some cases, it’s even harder. In 1998, Jay “Junior” Sigler was able to escape prison after his mother and her boyfriend rammed a truck through four prison security fences.
Sigler and a friend were able to jump through the fence and into his mother’s car, which was waiting just beyond it. The two convicts were caught the next day after they had crashed into another car and killed the driver, 55-year-old Dennis Palmer. Both were given life sentences as a result of their deadly escape.
17. Alfréd Wetzler and Rudolf Vrba
This prison outbreak is unique in that it was not done by convicts, nor criminals — but victims of one of the cruelest acts in history. Auschwitz concentration camp was the largest and deadliest of the Nazi World War II extermination camps. But two Slovakian Jewish slave laborers, Alfréd Wetzler and Rudolf Vrba, were able to escape and save the lives of thousands.
In April 1944, the two hid in a hollowed-out space inside a pile of wooden planks set to be taken outside of the prison’s grounds. They hid there without food or water for four days, until search parties were called off. Once they emerged, they headed by foot for the Slovakian border. There, they managed to sneak out a report to the Allies, the first eyewitness account they had heard about the horrors taking place in Auschwitz. The report led Hungarian officials to stop deporting Jews to Auschwitz, saving about 200,000 lives.
18. Brian Bo Larsen
Brian Bo Larsen may hold the record for the most prison escapes in history. In total, the Danish criminal has managed to escape prison 22 times. His methods have ranged from using tools like saws to break through bars on windows, to hiding in trashcans before they were taken off of prison grounds.
Perhaps Larsen’s most elaborate scheme came when he was able to get his hands on a bulldozer that was left on prison grounds. Larsen drove the bulldozer through the outer walls of the prison, freeing himself and 13 others. But while Larsen might be great at breaking out of jail, he was not as successful at keeping himself out. He was caught later on after stealing a car.
19. Pascal Payet
What is more epic than one helicopter-related prison break? Three helicopter-related prison breaks. Convicted French murderer Pascal Payet broke free from prison in 2001 when he made his way to the prison roof and was picked up by helicopter by his friends. But that just was not enough for him.
Two years later, he came back to the same prison to help three more convicts escape via helicopter. And as if the story is not bizarre enough, Payet was later caught and managed to escape yet again during a Bastille Day celebration. This time, four masked men hijacked yet another helicopter for his escape. He was captured and was transferred to a prison in an undisclosed location.
20. Sarah Jo Pender
In 2007, convicted murderer Sarah Jo Pender had exhausted all of her appeals. She would later say that “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.”
That escape came in 2008, when Pender hid in the backseat of her prison guard lover’s car as he drove off of the prison grounds. She was then transferred to the car of her former cellmate, and ultimately settled into the North Side of Chicago. She was caught once her neighbor recognized her during a rerun of the show America’s Most Wanted.
21. Rédoine Faïd
French gangster Rédoine Faïd was serving time for a botched armed robbery when he made a stunning escape from prison. Three of his accomplices had hijacked a helicopter after pretending to be flight students, and they forced the pilot to assist in Faïd’s escape. Police found the helicopter abandoned after all the men involved fled using a getaway car.
Faïd quickly became France’s most wanted criminal. Three months after his escape, Faïd was apprehended once again by police. This was his second prison escape; during his first escape, he had used dynamite to blast through five prison doors and escaped using yet another getaway car.
22. 75 of Paraguay’s Most Dangerous Criminals
It was called “the biggest prison break from our facilities” by Paraguay’s justice minister. In January 2020, in the early hours of a Sunday morning, 75 criminals — including 40 from a Brazilian drug cartel known as Primeiro Comando da Capital (or PCC) — escaped a Paraguayan prison by way of an underground tunnel.
At the time of their escape, authorities said that it was “clear” the prisoners were aided by prison guards. In fact, the prisoners were digging their tunnel so openly that some officials believed it may have been a ruse to take responsibility off of the guards. The criminals might have actually been able to walk right out the front door. At least five guards were suspended.
23. Dieter Dengler
German-born Dieter Dengler was a US Navy pilot fighting in the Vietnam War when his plane was shot down and he became a prisoner of war. He and other prisoners were forced to eat rats after food rations were waning, and every night their feet would be locked to blocks. But he quickly learned how to pick the lock, hatching his ultimate escape plan.
As North Vietnamese guards ate, Dengler and his fellow prisoners broke free and stole ammunition. A gunfight ensued, and he and a fellow escapee fled into the jungle. At one point, a machete-wielding local killed Dengler’s companion. Dengler was ultimately rescued by a fellow American pilot who had spotted him collapsed in a river, 6 long months after Dengler’s plane was initially shot down.
24. Víctor Manuel Félix Beltrán, Luis Fernando Meza González, and Yael Osuna Navarro
In January 2020, three high-profile inmates in Mexico City escaped from penitentiary. All of the inmates had close connections to drug lord Joaquín “El Chapo” Guzmán, and one of them was said to be the financial chief of El Chapo’s Sinaloa Cartel. The escape made international headlines, as all three were waiting to be extradited to the United States.
In the aftermath, two high-ranking prison officials and 16 prison staffers were reported to be under investigation. Reports said that “there had clearly been collusion with the prison staff,” considering that the prisoners would have had to break through five separate security barriers in order to escape.
25. “The Great Escape”
During World War II, thousands of prisoners of war were held in the Nazi-controlled Stalag Luft III camp. Little did the Nazis know, about 600 prisoners were planning escape routes. Thirty feet below the camp, the prisoners had built three pretty impressive 2-foot-wide tunnels, named Tom, Dick, and Harry. They used tin cans and candles to scoop soil, and propped up the walls with bed boards.
On March 24, 1944, the escape began. Quickly, the first prisoner out of one of the tunnels noticed that it had not been dug far enough. The tunnel’s exit stretched just before the tree line, leaving them vulnerable. In total, 76 men successfully fled, before guards finally noticed the 77th attempted escapee.
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