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The 15 Most Dangerous Criminals Who Ever Escaped Prison

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The 15 Most Dangerous Criminals Who Ever Escaped Prison

We all know what prisons are supposed to do – keep dangerous criminals behind bars. But sometimes the seemingly impenetrable walls of our most secure correctional facilities fail miserably. It seems almost inconceivable that common criminals could find a way to escape their fates… But then again, the criminals on this list aren’t your average low-brow thieves. The people on this list are some of the most dangerous people that the world have ever seen. That’s what makes it all the more alarming that our prestigious law enforcement agencies were not able to properly keep the secure. Some of these criminals even continued to commit more crimes after their escape.

As bad and as dangerous as these people are, it takes a real genius to escape from a prison. Although their crimes are despicable, in some way you have to admire their sheer determination and cunning in their attempts to escape. Sometimes it’s as simple as bribing the right people. Other times, inmates hatch elaborate crimes that could only be executed by some of the most intelligent people alive. It’s an interesting phenomenon that serial killers and sociopaths who commit brutal crimes often have some of the highest IQs. Crime doesn’t pay – except the price of having to spend your life behind bars. But these criminals almost got away without facing the consequences of jail time.

15. El Chapo – Most Powerful Man In Mexico

By far the most dangerous and feared criminal in all of Mexican history was Joaquin “El Chapo” Guzman. He was the most powerful man in the Mexican cartel for many years, and he became as famous for breaking out of prison as he did for his brutal crimes. He acted as the head of the infamous Sinaloa Cartel for many years, and some even called him the most powerful man in Mexico. He ran a drug empire that smuggled an estimated 500 tons of cocaine into the United States alone. He was first captured in 2001, but escaped inside a laundry cart. He bribed several people to aid his escape, including a prison guard that electronically opened his cell door as the laundry cart went by. He was wheeled straight out of the front door. 13 years later, he was caught once again, but was only kept for a few months before he escaped once again through a tunnel that led straight to his prison shower. In January 2016, he was caught once more, and he now faces charges in the US.

14. David Sweat And Richard Matt – Killers Digging Extensive Tunnels

These two convicted killers performed one of the most daring and brilliant escapes in prison history. Richard Matt was no stranger to escapes, and he had performed many during his life of crime. In 1986, he escaped from Erie County Correctional Facility where he was serving a one year sentence for assault. He climbed over the walls and evaded police for days before he was recaptured. Many years later, he killed his boss with his bare hands, breaking his neck, a crime for which he was imprisoned. He and David Sweat, another killer, were given large cells because they had been following the prison rules carefully for years. They then smuggled in hacksaws and other tools, digging an extensive tunnel through steel walls that led them to a manhole in Dannemora, New York. They were able to evade authorities for a few days before they were shot by police, who were conducting a nation-wide manhunt for them. Only David Sweat survived.

13. Frederick Mors – Escaped From An Asylum 

Frederick Mors was one of the most dangerous serial killers in history. He was an Austrian immigrant to New York City who worked in a nursing home from 1914 to 1915. During this time, he killed and poisoned 8 elderly patients. He used arsenic and chloroform to kill his victims. When confronted by police, he confessed to his crimes and was almost proud of his actions. The authorities then deemed him insane, transferring him to an asylum. Inevitably, he escaped from the asylum. The most disturbing thing about this is that he was never recaptured. He escaped from the Hudson River State Hospital in 1916. To this day, no one knows what happened to this serial killer. He could have killed more people for all we know. It seems inconceivable that the police would put such a dangerous killer into a facility with such little security. Let’s hope they learned from their mistakes.

12. John Dillinger – Smuggled Guns Into Prison

John Dillinger was one of the most famous gangsters of the American depression era, and committed many crimes. He was most famous for robbing banks, of which he robbed 24 during his criminal career. He also once shot a policeman, killing him through his bullet-proof vest during a shootout. His escape from prison was every bit as daring as his many bank robberies. Dillinger met 6 other criminals while in the Allen Country Jail in Lima, and led them in a plan that would lead to their eventual escape. Dillinger arranged guns to be smuggled into the prison from the outside. Part of his gang then showed up, impersonating police officers, and claimed they were there to extradite Dillinger. They were able to secure the release of their leader, and promptly shot anyone who got in their way, securing Dillinger’s first escape.

He was once again captured one year later, and incarcerated in what police called an “escape-proof” prison. This was the Crown Point Jail. No one really knows quite what happened on the day of his escape or what exact methods Dillinger used. FBI files suggest that the bank robber carved a fake pistol out of a potato, and used it to escape, but some say that the gun was real. He spent the next few years evading the police, even getting plastic surgery at one point. Finally, he was shot dead in a shootout at a theater.

11. Richard Lee McNair – Plan Ruined By A Tree Branch

Richard Lee McNair was a killer whose escape attempts became more famous than his actual crimes. He killed a man in a botched robbery, and injured another man after shooting him 4 times. During the authorities’ attempts to incarcerate him, he escaped three times from three separate facilities. His first escape occurred shortly after he was arrested, at Minot municipal police station at Minot Air Force Base. He used lip balm to squeeze out of his handcuffs and made a run for it. He was cornered on a roof top hours later, and tried to jump onto a tree branch to escape. The branch broke, and he hurt his back, allowing the police to capture him. He was then transferred to North Dakota State Penitentiary where he made his second escape. He escaped with two other inmates through a ventilation duct, and evaded police for ten months.

But his final escape was by far the most impressive. After he had been recaptured, he was transferred to a US penitentiary in Louisiana. Ten years after his initial incarceration, he made his final escape. He got a job in the prison repairing torn mailbags, and one day he wrapped himself in a specially constructed escape pod with a breathing tube, which was buried under a pile of mail bags. The pod was then shrink-wrapped and mailed out of the facility. He is the only known inmate to successfully “mail himself out of prison.” He evaded capture for many years, and crossed the border to Canada. Unfortunately for him, he was captured by the RCMP and shipped back into the US, where he is currently being held. But don’t rule out another escape.

10. Ricardo Caputo – Easily Escaped Mental Asylum

Ricardo Caputo was 45 years old when he turned himself in to police, 20 years after his escape from a mental institution following the murder of several women in the 70s. Shortly after moving from Argentina to New York, he met Natalie Brown, who he started dating. Soon Ms. Brown was found stabbed to death, and Caputo was arrested. But the authorities made the fateful mistake of declaring him mentally unfit to stand trial, and he was sent to a mental hospital instead of a prison. He was treated by a psychologist called Judith Becker. He was allowed furloughs after a time, and he would show up at Judith Becker’s property. Although the psychologist tried to befriend the killer, she was later found beaten and strangled with a stocking. He fled with the psychologist’s stolen car to San Francisco, where he took up another identity and killed another woman. He then went to Mexico City, killing yet another woman. He was a suspect in many other murders as well, and finally turned himself in because his crimes were beginning to haunt him.

9. Donald Leroy Evans – Overpowered A Guard

Donald Leroy Evans is one of the most dangerous, despicable criminals ever to escape custody. This man was an avowed white supremacist, and he has a fearsome reputation. He was first arrested for rape in 1986, and served 5 years in prison. After his release, he floated around, taking various different jobs before raping and murdering a 10-year-old girl he picked up in his car. He was given the death penalty, and incarcerated in Harrison County Jail. He and three other inmates managed to overpower a guard and threaten him with a shank before successfully escaping from the prison. Evans was found hiding in a shack a mere 800 meters away from the prison. He was later stabbed to death by a fellow death row inmate in 1999, before he could be executed.

8. Rodney Halbower – Escaped Through The Fence

The only thing more disturbing than Rodney Halblower’s crimes is the fact that he managed to escape twice. It all started when he was out on bail for raping a blackjack dealer. He used his newfound freedom to rape and murder at least 6 women in the San Francisco area. After he was finished with the murders, he went back to Nevada to stand trial for the rape he had committed. No one knew that he had committed the murders while out on bail. He was put in prison, but managed to escape during a softball game that the inmates had organized. He escaped another time with the help of another sex offender, and they climbed a wall and cut holes through the fence to escape. He then stabbed a woman 19 times while trying to steal her purse. She survived. He was caught and put back in jail, this time for attempted murder, and was released in 2013. Then, he had DNA samples taken which proved he was behind the 6 murders all those years ago.

7. Bartolomeo Gagliano – Let Out To Visit Sick Mother

For some reason, Italian police kept on underestimating Bartolomeo Gagliano’s capacity for murder, and it cost several people their life. This serial killer first got his start in 1981, when he beat a prostitute to death with a rock. He was sentenced to 8 years in a mental institution. He escaped, and took an entire family hostage. He was put back in an asylum, but inevitably broke out with the help of another patient. This time, they shot and killed two transvestites and almost murdered a female prostitute. He was put back in the asylum and served his sentence until release. Then, he was put in prison for extortion. Police thought he was just a common thief, and had no idea of his murderous past. So they allowed him to leave the prison to visit his sick elderly mother. He went on another rampage, and when he was finally captured he committed suicide in his jail cell by hanging himself with his bed sheet.

6. Allan Legere – Asked To Use Bathroom Alone

America’s northern neighbor has also been caught off guard by resourceful escapees. One such example is Allan Legere. He was first arrested for beating an elderly shopkeeper to death. But he didn’t stay incarcerated for long. In 1989, he was transferred to a hospital for an ear infection. He convinced the guards to let him use the washroom alone, and picked the lock on his handcuffs with a lock pick he had hidden inside of a cigar. He then beat off the guards with a television antennae before escaping the hospital property via carjacking. For seven months, Legere was at large and he committed four more murders. He was finally caught after over 201 days of rampaging across New Brunswick. Inexplicably, he is now being held in a minimum security penitentiary.

5. Earle Nelson – Escaped With The Help Of A Rusty Nail

Earle Nelson is another serial killer with a talent not only for murder, but also grand escapes. It all started when he suffered a massive head injury as a child that left him in a coma for 6 days. When he woke up, he was never quite the same, and he acted erratically and strangely from that day forth. He was escaping out of mental hospitals from a very young age, until he was finally released. He then tried to molest a 12-year-old girl, but was caught and once again put in a mental hospital. He once again managed to escape multiple times, until he was finally released.  That’s when he started killing people. He killed at least 26 people, mostly targeting land ladies because he could easily enter their home by pretending to be interested in renting their property. He would often engage in necrophilia with the bodies, and hide them under beds when he was finished. He was arrested in Canada and was placed in a jail cell, only to escape using a single rusty nail. He unwittingly boarded a train full of police officers, and was arrested one final time before he was hung in 1928.

4. Lyda Trueblood – Model Inmate Gets Cut Some Slack

The only woman on this list managed to kill multiple men and make numerous escapes. Things got strange when everyone in her entire extended family got sick and died. She then moved on to another husband, and another, and another, until she had married 4 different men, all of whom died of the strange mysterious sickness. Police examined the bodies of her latest husband and found evidence of Arsenic poisoning. They tried to track her down, but she had fled to California, where had married another man. Lyda’s scam was simple – convince her husband to get a life insurance policy, kill him, and take the money. When they finally arrested her, she became the model prisoner in jail. They relaxed the rules for her, and she broke out of her jail window and used bed sheets to rappel down the wall to a waiting man in a car. They found her trying to convince her sixth husband to get life insurance.

3. Randy Greenawalt And Gary Tison – Carjackings And Dehydration

Both of these men were in jail for brutal crimes when they escaped. Gary Tison killed a cop who shoved his wife. Randy Greenawalt was arrested for the murder of at least three truckers. Gary Tison made one failed escape attempt before he met Greenawalt, killing a correctional officer in the process. In 1978, three of Greenawalt’s sons smuggled pistols and shotguns into the prison via a cooler. Greenawalt and Tison were able to use the firearms to lock the prison guards in a closet before walking out in civilian clothes. They hooked up with Greenawalt’s sons, and drove away. But they suffered a flat tire, forcing them to carjack a family of four, including 2 children. They killed the entire family, and then later carjacked a married couple, killing them as well. They were stopped at a police roadblock and everyone except Gary Tison was arrested. He died of dehydration in the desert after attempting to flee on foot.

2. Ted Bundy – Jumped Out A Window

Ted Bundy is one of the most famous serial killers in American history, not least because of his many escape attempts. He was first arrested for kidnapping, and he was given access to a courtroom library to prepare his defense. He then jumped out of a window, but was recaptured days later. He was later able to slip through a small hole in his prison cell ceiling. While he was on the run, he entered a sorority house and beat two women to death, injuring two others. He then went to a nearby house and beat another student to within an inch of her life. When police responded, Bundy was already gone. He then kidnapped and killed a 12-year-old girl. Almost all of his victims were sexually assaulted or raped, and he engaged in necrophilia with some of the bodies. In the end, he was captured and executed in 1989.

1. Shaun Colin Walmsley – Gang Helped Break Him Out

The last murderer, Shaun Colin Walmsley, is perhaps the most disturbing criminal on this list. Not because of the nature of his crimes, but because of the fact that this man from Liverpool is still on the loose. He was serving a 30 year sentence for stabbing a rival drug dealer to death, and had to be transported to a medical treatment center. Somehow, this drug dealer got the word out to his gang, and two of his most faithful men showed up at the hospital with guns and knives, threatening the police and medical staff to release the prisoner or face death. The men all got away, and they were last seen speeding away from the hospital in a Volkswagen Golf. This just goes to show that prison escapes aren’t something that happened only in the old days of the wild west and the prohibition era. Killers are escaping every day, and some are on the loose as you read these words…

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