For most rational people, the threat of going to prison even once is all it takes to stop them from ever committing any crimes. Of course, it could also be said rational people wouldn’t do anything to wind up behind bars in the first place. Those amongst us more inclined toward lives of crime seemingly can’t resist the urge, regardless of any punishments they may face because of it. Sometimes, even getting caught and spending a couple years in jail aren’t enough, but then again, to certain criminals, prison doesn’t seem like all that big an obstacle.
Though the entire point of prison is to keep violent and dangerous criminals away from society, it would turn out quite a few of them have failed at achieving this goal. Everyone has seen a movie or two featuring a prison break, and believe it or not, the real deal is almost as common as the Hollywood version. In fact, prison breaks are so common in real jails that certain men have managed to build a reputation for being particularly good at it.
Obviously, there’s a huge downside to this trend in that nine times out of ten, criminals only escape from prison to get back to doing what they love most—being criminals. On the plus side, criminals who get caught once are usually bound to get caught again, and almost everyone to escape from jail was sent back there in short order. Unfortunately, this doesn’t take back any damage done in between their escape and recapture, especially when lives were lost in the process. Keep reading to learn about 15 prisoners who escaped from jail and kept committing crimes.
15. Ted Bundy – Serial Killer
One of the most vicious serial killers in American history, Ted Bundy’s name is synonymous with real-life horror. Using little more than his charm and good looks to lure female victims into his arms, Bundy was a horrifically prolific murderer, claiming responsibility for taking over 100 lives although only around 30 have been confirmed. In addition to the uncertainty related to the number of victims, no one is entirely sure when Bundy’s killing spree began, though it’s known he was first arrested and sentenced to jail for kidnapping and assault in 1976. At the same time, he was facing a separate trial for a separate murder, and he managed to escape a courthouse by acting as his own attorney, thus granting him access to the library, from where he jumped out the window. Bundy was soon recaptured, only to make a second escape barely a year later. This time, he evaded capture long enough to resume terrorizing women, taking at least three more victims before getting caught a third and final time. His many crimes finally having caught up with him, Bundy was sentenced to death and executed in 1989.
14. El Chapo – Gang Leader/Drug Kingpin/Murderer
Outside of perhaps Pablo Escobar, it’s possible no one in history has made more money off of the illegal drug trade than Joaquín Guzmán, better known by his criminal name, El Chapo. En route to controlling the Colombian cocaine trade, El Chapo also murdered plenty of his rivals and ordered the deaths of countless more. Due to these crimes and his drug-trafficking empire, El Chapo has been a highly wanted fugitive since the 1980s, though his life of crime truly began a decade before that, working for Hector Palma, aka El Güero. It wasn’t until Chapo took over on his own that the crime spree really took off, though, thus causing the increased police interest in his activities. Chapo was first caught in 1993, when he was sentenced to 20 years for drug-related offenses. Though he remained a top drug lord from prison, Chapo wasn’t satisfied behind bars, easily bribing his guards to make an escape in 2001. After spending 13 years on the lam back on top of the drug empire, Chapo was recaptured in 2014, only to again escape the very next year. Mexican authorities were especially incensed by this second successful exit, intensifying their search and capturing Chapo yet again about six months later.
13. The Texas 7 – Gang of Murderers/Thieves
When a single criminal escapes from prison, there’s always a small chance they’ll legitimately live the rest of their life without ever committing a crime, terrified doing so will send them back to jail. On the other hand, when seven criminals conspire to escape prison together, a full-fledged crime spree is bound to follow. This was the case with the Texas 7, a gang of prisoners who escaped from a Texas jail in late 2000. Most members of the gang had already been convicted of violent crimes, and this would only intensify after they escaped by impersonating staff and stealing a prison maintenance truck as their getaway vehicle. Once out of prison, the Texas 7 sustained themselves by robbing several stores, including a Radio Shack and an Oshman’s Sporting Goods. During the second robbery, things would escalate to murder when a police officer was killed on the scene. From there, America’s Most Wanted aired an episode about the gang, directly leading to their capture when viewers of the show spotted several members in Colorado. All were recaptured and sentenced to death for their escape and the murder, except for one member who killed himself during a police standoff.
12. Steven Jay Russell – Insurance Fraud And Embezzling
Lots of the stories on this list sound like they deserve a movie or two, and yet Steve Jay Russell’s example proves the bar is pretty high for making that happen. There’s also the fact his crimes were initially relatively light and never became violent, with the main reason he’s stuck in solitary confinement for the rest of his life related to the fact he’s an expert at escaping from jail. Before Russell could start escaping from jail, though, he had to get sent there in the first place, and thus, his story begins with a minor charge of insurance fraud. While in jail, Russell met and fell in love with Phillip Morris, and when the two were released, he made it his goal to give Morris whatever his heart desired. Of course, this required lots of money, and so Russell resumed his criminal activities, committing countless acts of fraud, embezzlement, and impersonation, getting him sent back to jail. Mostly in an attempt to reconnect with Morris, Russell would then escape from jail no less than four times, always in highly creative fashion. Morris would always be his downfall, though, as Russell basically led police right to him by always trying to track his lover down.
11. Richard Lee McNair – Murderer/Car Thief
There’s not much positive to say about Richard Lee McNair’s personality, but we gotta give this much to the man—he’s a pretty creative escape artist. After landing behind bars in 1988 due to a robbery that turned into a murder, McNair’s first plot to get out of prison put him into MacGyver territory, in that all he needed to pull it off was chap stick. Somehow, McNair rubbing said item all over his wrists allowed him to slip out of handcuffs, and running like hell was all it took from there. McNair didn’t get far that time, recaptured in mere hours, but four years later, he tried again by making his way through a ventilation duct. He evaded recapture for nearly eight months, resuming his life of crime by stealing countless cars while constantly changing his identity to evade recapture. Police finally caught him, only for McNair to escape for a third time in his most creative ploy yet: smuggling himself out through a pile of mail. McNair made it all the way from North Dakota to Canada before police caught him and sent him back to prison, where he currently resides.
10. Andre Stander – Bank Robber
Unlike everyone else on this list, there’s little surprise Andre Stander knew a thing or two about how to escape his prison cell—up until his initial capture, he had himself been a police officer all his life. Ironically, this is what made Stander decide to start robbing banks instead, feeling superior to his co-workers and especially his father, who had forced him into the job. Between 1977 and 1980, Stander stole nearly 100,000 South African rand from various financial institutions, and to really rub it in to his fellow officers, Stander did this during his lunch breaks. After almost 30 successful bank jobs, Stander was caught and given a lengthy jail sentence, but still harboring bitter resentment against the police, he wasted little time in proving he could outsmart them again via making an escape. As he no doubt expected, Stander easily fled from his prison cell with two other inmates, with whom he then formed a gang that successfully ripped off another 20 banks in a manner of mouths. The police hot on their trail, the gang soon broke up and fled to separate locations across the globe. Stander wound up in Florida, where he was gunned down by a police officer.
9. Jack Sheppard – 1700s Thief
Obviously, any story that takes place in the 1700s is going to be a whole lot different than the other modern-day examples featured on this list. For starters, the crimes committed by petty thief Jack Sheppard were far less severe than the other criminals on this list, rarely amounting to more than robbery and a passion for women of the evening. Of course, he also found it fun to escape from prison, doing such no less than four times in his short 22 years on this Earth. The first time around, the police had no one to blame but themselves, locking Sheppard in the same cell as his girlfriend and making it easy for them to work together and climb out of a window. That same girlfriend helped him escape a second time, and a third jailbreak was accomplished by want of a single crooked nail that helped him remove his handcuffs. After that many escape attempts, the English government decided the only fate left for Sheppard was death by hanging, and he was executed in in 1724 after getting caught yet again, allegedly too drunk to resist arrest.
8. Seamus Twomey – Ordered Car Bombs
While the Irish Republican Army’s pronounced goal is Irish independence from the British government, their methods of achieving this have, at times, been dangerously violent, once leading a massive car bombing campaign throughout the streets of England. One of the earliest and most prominent members of the IRA was Seamus Twomey, Officer Commanding during Bloody Friday, a 1972 bombing spree that took the lives of 9 people in Northern Ireland, also injuring more than 100 others. For his role in this event, Twomey was sent to jail, only to escape within months via helicopter with the help of fellow IRA members. From there, Twomey resumed his high-ranking position in the organization, allegedly giving the go ahead for another terrorist event called the Kingsmill massacre, where 10 more people were killed. He was captured again in 1977, serving five years in prison. The short sentence can only be explained by his distant role in the events, never actually committing any killings and only accused of ordering them.
7. Daniel Camargo Barbosa – Child R—-st
It could probably be argued that a few of the criminals on this list were more or less forced to keep committing crimes in order to evade recapture, not that this in any way defends their actions. That said, the actions of Daniel Camargo Barbosa were nonetheless demonstrably worse than any crimes of necessity or opportunity, as he spent his entire sentence dreaming about escaping to wreak more havoc. Barbosa’s particularly vicious crime was sexually assaulting and murdering young girls, amassing more than 80 victims in his native Colombia before his initial arrest. Amazingly, this horrific spree only earned him 30 years in prison, which he was supposed to spend in an island prison known as the Colombian Alcatraz. Somehow, Barbosa made his escape on a poorly assembled boat, and prison guards soon gave up their search assuming there was no way he could evade getting eaten by sharks on his journey. Tragically, he not only survived the sharks but made it all the way to Ecuador, where some 72 more victims were sexually assaulted and killed. Barbosa was finally caught again only moments after taking his last victim’s life, after which he was killed in prison by another victim’s relative.
6. John Dillinger – Gang Leader/Bank Robber
Ironically, according to the man himself, John Dillinger’s life of crime didn’t truly begin until he was arrested for a very minor robbery. Expecting leniency from the judge, Dillinger confessed to stealing $50 from a local grocery store in 1924, earning a whopping 10 years behind bars for the petty crime. While in prison, Dillinger became highly interested in gang life, and by the time he was ready to get out, he had a ready-made crew of bank robbers prepared to help him become the new kingpin. Dillinger and his gang pulled off 12 successful robberies in the span of a year after their release in 1933, during which time Dillinger himself was caught and sent to prison twice. Of course, he managed to escape in short order both times, quickly resuming his bank-robbing ways with all-new gangs supporting him each time. Eventually, though, Dillinger met someone he couldn’t rely on in brothel-owner Anna Sage, who helped lead the FBI to his location. Dillinger died in a shootout with police not long afterward.
5. John McCluskey – Murderer
Though he initially had the shortest rap sheet between himself, Tracy Province, and Daniel Renwick, it was John McCluskey who devised the plan for all three to escape with the help of his cousin Casslyn Welch. The three were all in jail for various violent crimes — Province and Renwick murder, McCluskey attempting to do the same in addition to other crimes. Once they broke out of prison, the men went their separate ways, with Renwick caught before he could commit any further crimes. McCluskey and Province, however, stayed together long enough to kill two more people while also stealing their car, later setting their bodies on fire to dispose of evidence. Province was apprehended soon after this while McCluskey kept his spree going with Welch in tow, the duo robbing a beauty salon. Shortly after that, the duo was caught at a Ski Resort, and all involved parties were sentenced to long stints in prison for their various crimes.
4. Willie Sutton – Bank Robber
The mere fact a man is a professional bank robber doesn’t necessarily make him that bad of a person. Sure, Willie Sutton terrorized his share of tellers when stealing more than $2 million from them, but his fellow gangsters always considered him a stand-up fellow who despised actually resorting to violence. According to the man himself, the gun he used to rob banks was never even loaded. True to form, there are no violent crimes on Sutton’s record, but that much stolen money is bound to capture police attention, and he was caught in 1931, sentenced to 30 years in prison. Only a little over a year later, Sutton escaped by holding a guard hostage and procuring a ladder to scale the walls. After escaping, Sutton resumed to robbing banks, though he wasn’t quite as good at it as he was previously, getting caught after a mere two scores. Sutton would escape twice more, both times lowering his activity in the crime world, albeit not enough to avoid recapture.
3. Brian Bo Larsen – Car Thief
Everyone else on this planet considering themselves an “escape artist” might as well call it quits right now because no one will ever top the feat accomplished by Denmark’s Brian Bo Larsen. Setting one of those rare records Guinness wouldn’t dare print, Larsen has escaped from prison no less than 22 times, a fact made all the more shocking by the relatively minor crimes he had committed before taking up this hobby. Outside of repeatedly escaping prison, the only crimes on Larsen’s rap sheet are car theft, petty robbery, and violence against police officers, the last of which only occurred during his many, many arrests. Most amazing of all, Larsen has apparently accomplished all of these tasks while bombed out of his minds on various drugs, as his most recent recapture saw him drive a stolen van through a fence while hallucinating he was fighting imaginary people.
2. Vassilis Paleokostas – Kidnapper
Although Robin Hood will forever be viewed as a folk hero for stealing from the rich and giving to the poor, things would probably be a little different if instead of stealing, the Sherriff of Nottingham were committing some harsher offense. This is why Vassilis Paleokostas is nonetheless considered a criminal despite only focusing on wealthy, high-profile marks, as a person’s bank account hardly justifies terrorizing them in any way. Paleokostas twice kidnapped billionaires and demanded huge ransoms, which he got, ultimately leading to his downfall when police tracked the money back to him. The second of these kidnappings didn’t even take place until after his first prison break, though, which he accomplished with the aid of accomplices hijacking a helicopter and flying him to safety. After the second kidnapping and arrest, Paleokostas did the exact same damn thing, this time evading fire from police officers who tried to stop him from flying away. Paleokostas is still at large and highly wanted by Greek authorities, yet his crime spree seems to have slowed down considerably, making it harder for them to catch him.
1. Michel Vaujour – Murderer/Bank Robber
Some couples won’t let a silly thing like one of them going to jail for attempted murder get between their love, and Michel and Nadine Vaujour apparently have this sort of relationship. To spring her husband from jail, Nadine learned how to fly a helicopter, taking one over his prison in 1986. Michel did his part in the escape by throwing nectarines painted to look like grenades at his guards, causing them to flee. Now, had the couple truly been romantic, this is where they would flee to an exotic island together and avoid crime for the rest of their lives. Unfortunately, it turns out crime was more important to the Vaujours than any sort of love-related business, as Michel was more interested in getting back to his life of crime. Nadine was soon captured on her own, while Michel was busy getting killed during a failed bank robbery.
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