Most Insane Ways People Have Escaped From Prison

Here's a controversial opinion: Prison is not very fun. It's almost like the whole place is intentionally set up as some kind of punishment or something! The food is garbage, the sleeping accommodations leave a lot to be desired, and the entertainment options are nonexistent. 

Boredom and unhappiness can be real issues in prison, since bored, angry inmates can start flights or even kill people. But other inmates use their copious amounts of free time and deep-seated frustrations in more creative ways, although still ones with which the powers that be would not look on favorably. With few ways to fill the hours of the day, some prisoners utilized their moral flexibility, complete and total disregard for natural selection, and excess of free time to plan the most impressive and certifiably insane prison escapes in human history. Some of them, instead of just daydreaming about it, even manage to pull them off.

Conman Steven Jay Russell had an impressive criminal career. Using nothing more than a bogus resume and a smile, Russell talked his way into the position of Chief Financial Officer for a large health insurance company, where he redirected funds into his wallet. After a clerical error revealed his creative accounting, Russell found himself in the Harris County Jail, where he met the love of his life, Philip Morris, who was due to be released soon.

Russell was not the type of person to let prison separate him from the man of his dreams and would go on to escape from prison on four different occasions to be with Morris. To walk out of jail, NPR reports that Russell made a guard's uniform for one successful escape, a doctor's uniform for another successful attempt, and once got a hold of a cell phone to convince a court clerk to lower his bail. Russell's last successful escape from a maximum-security prison was as insane as it was brilliant.

Russell used a crash diet and a supply of laxatives to simulate the rapid weight loss associated with a full-blown case of AIDS. Russell then arranged transfer to a minimum-security prison hospital, followed by a transfer to hospice care, where once again he walked out the front door. Not once did it occur to anyone to actually run tests on Russell to determine if he really had AIDS. While free, Russell sent a fake death certificate to a Texas court house, making him legally dead. Suspicious of the chain of events, police familiar with Russell thought everything was a little too convenient and began tracking Morris. When Morris and Russell reunited in Florida — by law a story this crazy needs to have some connection to Florida — Russell was arrested, and his original sentence was extended to 144 years. Russell's story is so crazy that it had to be adapted into a film, "I Love You, Philip Morris," and only an actor as graceful and dignified as Jim Carrey could do his story justice.

When most people think about living out their golden years in the south of France, the maximum-security prison in Grasse is probably not the destination that first comes to mind. Convicted murdered Pascal Payet, who was no stranger to prison escapes, was serving a life sentence when he decided that prison no longer held any appeal for him. Payet may have made some poor life choices that resulted in him serving a life term, but it turns out he did make some excellent decisions when it came to choosing friends.

One Saturday night in 2007, The New York Times reports the prison guards at Grasse were genuinely bewildered to see a helicopter landing on the roof of the maximum-security wing of their prison. Suspiciously, the helicopter landed on the one part of the roof without a clear line of sight from the guard towers. Four masked men got out of the helicopter and used heavy equipment to cut their way through the two heavy metal doors between them and Payet. Within five minutes of the helicopter landing — less time than it takes for an Uber to arrive — Payet and his crew escaped into the night.

This was the second time that Payet escaped from prison using a helicopter. What is surprising was the "Seinfeld"-esque breakdown in communications prior to the escape. Not a single person thought it was important the let the prison guards, who were holding a convict who had a penchant for helicopter escapes, know that a helicopter in the area was stolen. Payet's story is just a few explosions short from being the opening scene of a Michael Bay movie.

A 1962 escape from the Alcatraz Federal Penitentiary created the gold standard that all other insane prison escapes are now judged by. The architecture of Alcatraz was worthy of a supervillain's lair: the prison was built on an island, surrounded by freezing cold waters, and had one guard for every three prisoners. No one thought escape was possible until three inmates did just that. When the certified genius and bank robber Frank Morris became a guest at Alcatraz in 1960, he looked at the walls, ocean, and guards and thought that this would be a nice project to occupy some time. Enlisting the help of fellow inmates Allen West and the Anglin brothers, The NY Post reports the group would spend the next two years working on the most metal arts and crafts project in history.

Fake heads were made out of papier-mâché and hair from the barbershop to fool the guards during bed checks. Tools barely suitable for assembling an IKEA living room set helped the prisoners to access an unguarded ventilation shaft through the air vents in their cells. Opting to avoid the mistakes made in other escape attempts, like drowning, the group constructed a raft out of stolen and donated raincoats. With the small exception of West not being able to escape from his cell, all of the elements of Morris' plan came together perfectly, and the three other prisoners disappeared into history. The prison was turned into a National Park shortly after the escape, forever ensuring that Park Rangers could get a sweet gig in San Francisco

Sinaloa Cartel leader Joaquin "El Chapo" Guzmán left the planning and execution of his escape to capable professionals. For 13 years, El Chapo was on the run from Mexican authorities. During that time, El Chapo oversaw one of the largest drug smuggling operations in human history until his arrest in 2014. Compared to 13 years on the run, prison was practically a vacation for El Chapo. Regular bribes ensured that El Chapo spent his days enjoying the company of sex workers in the most luxurious prison cell money could buy. When extradition to the United States became a reality in 2015, El Chapo prudently decided to relocate.

Rather than getting his hands dirty with digging a tunnel or shooting his way out of prison, El Chapo had a tunnel built for him. As a man who enjoyed the finer things in life, El Chapo wanted the best escape tunnel in the world. The New York Times reports the result was 33 feet underground, nearly a mile long, 30 inches wide, and 5-and-a-half feet tall. If that wasn't impressive enough, the tunnel also had electrical lights running the entire length, plus a drainage and air filtration system. (What, no Starbucks at the midpoint of the tunnel?) When the time came for the escape, a motorcycle mounted on a rail provided quick transportation to freedom. The man actually escaped prison without breaking a sweat. It is amazing what unlimited funding combined with a complete lack of moral scruples can get you.

Brian Bo Larsen has the honor of simultaneously being one of the worst criminals and best escape artists that Denmark has ever produced. Larsen had spent the majority of his 20s and 30s in and out of prison for crimes ranging from theft to armed robbery. It is worth noting that The Washington Post reports prisons in Denmark are a little different from their American counterparts. The prisoners have comfortable cells, wear their own clothes, eat with their families once a week, and there is a noticeable lack of high walls, barbed wire, and shower stabbings.

Despite the comfort of Danish prison life, Larsen has chosen to escape, as of this writing, an astounding 22 times. In one instance, he borrowed a bulldozer and crashed it through the prison walls, freeing himself and 13 others. Larsen's most recent escape attempt reads more like a TMZ article than a crime report. After escaping from prison again and consuming roughly all of the drugs in Denmark, Larsen started partying with a local sex worker. After discovering that walking was difficult, the couple stole a car that was promptly crashed into a tree, and the escapee was quickly recaptured. Keep at it Larsen — one day you'll figure it out.

Neil Moore is perhaps one of the most dangerous people on the planet ... when he has a smartphone. Using nothing more than a cell phone, charm, basic knowledge of web design, and a natural talent for impersonations a "Saturday Night Live" cast member would sell their soul to possess, Moore talked dozens of gullible bank employees into handing him ungodly sums of cash. Moore's talents eventually landed him in a prison cell in the exceedingly British-sounding Wandsworth Prison. While most prisoners hustle to get their hands on cigarettes, pruno, or porn to make their stay more comfortable, Moore hustled for a smartphone, per the BBC.

With that small piece of technology that most take for granted, Moore planned a quick and clean escape. Using a technique known as typosquatting — registering a fake site with similar spelling to that of a real website — Moore built a pretty decent copy of the website for the Southwark County Court with his newly acquired smartphone. Moore then sent a pretty scary-looking email from the website's domain to the administrators of Wandsworth Prison, ordering his immediate release. Three days after walking out of prison, he turned himself in to the police and had 7 years added to his prison term. While most people would view this as a major life setback, Moore confidently returned to prison knowing that he could leave whenever he needed to. It's almost as if he turned himself in as part of some diabolical and intricate criminal plot concocted by a Bond villain ... oh dear.

In 1987, Richard Lee McNair was sentenced to a life term in prison after murdering a guard during an attempted robbery of, of all places, a grain elevator, per the CBC. Between 1988 and 2006, McNair would escape from prison three times. While his first two escapes were pretty conventional, McNair's last escape was simple, brilliant, and a little insane. After being transferred to a Louisiana prison, he got a job assignment repairing broken canvas mail bags. In short order, he hid in a pile of mailbags, which was later shrink-wrapped, placed on a pallet, and shipped to an unguarded warehouse.

While running away down a highway, carrying no identification and wearing prison clothes, McNair was stopped and questioned by Officer Carl Bordelon. What should have been a career highlight for Bordelon turned into YouTube gold as his dashboard camera recorded McNair spending 10 minutes talking his way out of what should have been the easiest recapture in prison escape history. At one point in the video, Officer Bordelon even mentioned that he was looking for an escaped convict before letting him go. McNair's luck did not hold out. He was recaptured, and has probably been workshopping his next escape ever since.

Movies like "The Green Mile," "The Shawshank Redemption," and the tragically underrated Will Arnett masterpiece "Let's Go To Prison" create the impression that prisons are staffed by sadistic bullies with massive inferiority complexes. In actuality, prisons are staffed by civil servants who have mind-numbingly tedious jobs. Prisoners Charles Walker and Joseph Jenkins noticed how the staff at the Florida State Franklin Correctional Institute would blindly obey whatever an official-looking form stated and got the idea to use the soul-crushing weight of the prison bureaucracy in their favor. CNN reports the pair created some rather impressive documents ordering their immediate release, and those orders were promptly obeyed.

Considering their rather limited computer access and the few materials they were allowed to have, their arts and craft project is all the more impressive. The release documents had signatures that matched those of an Orlando-based state attorney, as well as a judge. For good measure, the pair used the official seal of the Orlando County Clerk's office. Less than a month after their escape, the pair was undramatically recaptured in a Panama City motel room. Upon their return to prison, the state of Florida reevaluated the computer usage policy for inmates, no doubt earning them the everlasting thanks of every violent convict who could no longer go online to argue about movies and look at cat memes.

In jails and prisons around the world, the routine is everything. When an unexpected event like a power outage, late delivery, or one of the most famous gangsters of the day pointing a gun at a guard occurs, the routine collapses and everyone involved collectively panics. While in custody at the Crown Point county jail in Indiana, John Dillinger used a wooden gun to pull off one of the most insane prison escapes in American history.

Reports vary, but what the FBI says is that Dillinger used a wooden gun that even a LARPer would probably dismiss as unrealistic to get released from his cell, take at least three guards hostage, and then liberate two machine guns from the jailers. After his comedic change of circumstance, Dillinger locked the guards in his old cell and stole a car from the parking lot that happened to belong to the local sheriff.

This escape would prove to be Dillinger's undoing. By stealing a car and driving it across state lines, he committed a federal offense, so the FBI came after him with every resource available. So when Dillinger was murdering his way through the Midwest stealing everything that wasn't bolted down, he came out incarcerated, but unscathed. But violating the National Motor Vehicle Theft Act? That'll get you killed.

While some convicts have to spend years planning their escape, painstakingly sawing through bars or cutting holes in their cells, in other cases it seems like it would have been a miracle for an escape attempt not to happen. See: Lester Eubanks. In November 1965, Eubanks beat Mary Ellen Deener to death in Mansfield, Ohio, and the following year, a jury found him guilty of first-degree murder while perpetrating rape, and gave him the death penalty, (via the U.S. Marshals). However, following the famous Furman v. Georgia case, his sentence was reduced to life in prison without the possibility of parole.

One might think given the severity of his charges and original death sentence, that authorities would be extra cautious when dealing with him. Yet, just a few years later in 1973, they provided him with a golden opportunity for escape. That December, during the holiday season, prison officials took Eubanks to a local shopping center in Columbus to buy some gifts. As a reward for his good behavior while behind bars, they even let him wander off on his own with instructions to promise to meet them back in a few hours. Not surprisingly, Eubanks took the chance to make a break for it, and he has never been seen since. In early 2021, after his case appeared in a Netflix documentary, alleged sightings of Eubanks occurred in California, but authorities did not make any arrests (via the Mansfield News Journal).

In 2000, one of the biggest prison breaks in American history happened, when seven inmates teamed up to escape the Connally Unit in Kennedy, Texas (via History). Just a few weeks before Christmas, the group of inmates was all working together in the prison maintenance shop when they staged an uprising. They overpowered the guards and employees and stole a car before fleeing the scene, leaving behind an ominous note promising potential violence. They also took several weapons, including handguns, shotguns, an assault rifle, as well as copious amounts of ammunition (via the Texas Tribune). The inmates then looted a Radio Shack in Pearland, Texas, a few hours away from the prison, before robbing a sporting goods store weeks later in Irving on Christmas Eve. There they killed Officer Aubrey Hawkins in the commotion, before once again escaping, this time to Woodland Park, Colorado.

According to the Texas Tribune, during the sporting goods robbery, a witness had seen the break-in and they called 911 to alert the police. Hawkins was first on the scene and was shot to death almost immediately by five of the escapees at the same time. A month later, a tip led authorities to their location in Colorado, where six of the seven inmates were eventually captured after a brief standoff. All of the men were eventually convicted of officer Hawkins' death, and four of them have since been executed.

In the climactic scene of "The Shawshank Redemption," Tim Robbins' character Andy Dufresne escaped from the titular prison by carving a tunnel in his cell and crawling through a long sewage pipe to freedom. 

Twenty years later, at the Clinton Correctional Facility in Albany, New York, inmates David Sweat and Richard Matt developed a similar plan. Per NBC New York, the two inmates escaped in 2015 after cutting out the backs of their cells and crawling away through a steam pipe. Authorities immediately suspected they had inside help, because of how elaborate the plan was and the degree of skill it took to cut through the pipe, and it quickly came to light that prison guards had smuggled the inmates power drills encased in frozen hamburger meat (via Oxygen).

However, as soon as they got out of the prison everything started to go wrong. Not only did one of the prison guards fail to meet them at the pre-arranged spot, leaving them completely on their own, but Sweat and Matt started to have personal problems almost immediately. Matt was 14 years older than Sweat and in much worse physical condition, which made it hard for him to keep up (via ABC). In addition, Matt's penchant for alcohol and violence put him at odds with Sweat. Before long the two split up, and Matt was killed in a shootout. Sweat too was shot twice and captured, but he survived and went back to prison.

While many people associate the Isle of Wight with beautiful scenery or the famous 1970 album by The Who, if you're Keith Rose, Andrew Rodger, Matthew Williams — or countless law enforcement officers — you remember it for a 1995 prison break. According to the New York Times, the three men broke out of the Parkhurst prison on the Isle of Wight in January 1995 in a daring and bold escape. They used a duplicate "skeleton" key to open the back door of the prison gymnasium, before breaking into a prison workshop just across the yard. Using tools stolen from the shop, they cut through the fence and built a makeshift ladder to get over the back wall.

Police were completely mystified about how the men had gotten the key, which appeared to be homemade. Hundreds of police officers were on the scene, and they scoured the island looking for any signs of the men during the tense five days of their escape. Both Rodger and Rose had been convicted of murder, whereas Williams, just 25 at the time, was an arsonist and had originally gotten in trouble for poisoning people (per the Associated Press). Fortunately, they caught the three men within a week, including Williams twice since he escaped their custody again after he was initially caught (via The Independent).

While making up a fake doctor's appointment is a tried and true excuse for truant high schoolers trying to cut class, who knew it could also be used to escape from jail? Per CNN, inmate Casey White and Lauderdale jail guard Vicky White (no relation) used the ploy to escape from the Lauderdale County detention center in Alabama in April 2022. The two had met years earlier in 2019 when Casey, already serving a 75-year sentence, was in the Lauderdale jail after confessing to a 2015 murder while in prison.

They stayed in contact for years, and when Casey came back to the same jail in 2022 for more hearings on the 2015 murder case they rekindled their relationship. The two devised a plan where Vicky would transport Casey out of the jail under the guise of a fake doctor's appointment, and in late April they carried it out. The two were on the run for 11 days, during which they tried desperately to throw authorities off their scent. Eventually, though, authorities chased them down to Evansville, Indiana, where a brief pursuit ensued before they crashed and flipped their car. Police found Vicky with a self-inflicted gunshot wound to the head, and she died later that night. Casey survived the crash and was immediately transported back to prison. Charges were initially dropped but were likely to be reinstated after a grand jury hearing (via Al.com).