These Are The Craziest Prison Break Stories Ever

Even with 24-hour security, armed guards, razor-wire fencing, and observation towers, a number of inmates have escaped from prison during the last century. Prison escapes are some of the most dramatic events imaginable, so it’s no surprise that many of these escapes have inspired some of our favorite movies.

From Tupac’s aunt being broken out of jail with dynamite to the infamous crimes of John Dillinger, these prisoners gave us some of craziest prison break stories of all time.

Richard Lee McNair literally mailed himself out of prison!

Assata Shakur Achieves Political Asylum

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Assata Shakur was a member of the Black Liberation Army, which was underground criminal organization. The group was initially a part of the Black Panther Party before forming their group which believed in an armed struggle against the United States government.

In 1977, Shakur was convicted of aiding and abetting the group during a shootout which resulted in the death of State Trooper Werner Foerster. Two years later members of the BLA broke her out of prison by using pistols, a stick of dynamite while holding two guards as hostages. The group stole a van and was able to escape without anyone being injured. She was immediately sought by the FBI although many citizens in the area welcomed her to the area. Shakur ultimately fled to Cuba where she was granted political asylum and still remains today. Interestingly, Shakur was also the godmother of Tupac Shakur, the late 1990s rapper.

Sarah Jo Pender Seduced A Guard

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Sarah Jo Pender was in prison for her role in the double homicide of her former roommates. Despite the evidence, Sarah has maintained that she was wrongfully convicted. Not okay with staying in prison, she planned her escape with the help of correctional officer Scott Spitler.

Scott provided her with a cell phone and clothes and personally drove her out of prison in a van. Correctional officers identified Scott as her accomplice through surveillance tapes, and he was sentenced to eight years in jail. America’s Most Wanted ran an episode that featured Sarah who had since moved to Chicago working for a contractor under the name Ashley Thompson. After recognizing her in the episode, a neighbor alerted the police and Sarah was arrested.

The Elusive Steven Jay Russell

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In the early 1990s, con artist Steven Jay Russell was arrested for fraud after faking a slip and fall accident. His first escape from jail came in 1992 when he pretended to be an undercover police officer. Steven wanted to escape because his boyfriend Jim Kemple was dying. The two fled to Mexico City but returned to the U.S. as Jim’s health declined.

Steven was captured, and Jim died three weeks later. While in jail, Steven found a new love named Phillip Morris. Steven and Phillip were eventually released prison, but Steven resumed his bad behavior. He lied on his resume and got a job as the chief financial officer of the North American Medical Management (NAMM) and began embezzling funds. Steven purposely targeted NAMM because he blamed them for not covering specific treatments for his deceased boyfriend, Jim. He and Phillip were both arrested.

With a little creativity, Steven literally walked out of jail. See how he did it next.

Steven’s Life Inspired I Love You Phillip Morris

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Steven escaped again — this time by impersonating a judge over the phone and lowering the bail so he could afford to pay. He was caught three days later. Still unwilling to stay in jail, he dyed his prison clothes with green highlighters and toilet water to mimic doctors scrubs. He walked out of prison. He reunited with Phillip, and they fled to Mississippi but were found ten days later.

Steven staged one last escape by losing weight to make it seem as though he had AIDS, even using a typewriter to falsify his medical records. He was given special needs parole and sent to a nursing home for hospice care. Steven continued his schemes, calling the nursing home impersonating a doctor who was offering experimental AIDS treatment. Still pretending to be ill, accepted the treatments and left the nursing home. He then sent the prison a death certificate. A movie has since been made of his crazy life called I Love You Phillip Morris starring Jim Carrey and Ewan McGregor.

Richard Lee McNair Mailed Himself Out Of Prison

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Convicted murderer, Richard Lee McNair, escaped three different times from different jails under extremely bizarre circumstances. In his first escape, Richard used lip balm to help him squeeze his hands out of a pair of handcuffs. During his second escape, he crawled through a ventilation duct. The last escape occurred when he managed to mail himself out of prison in a crate.

As a result of his last escape, he was featured on America’s Most Wanted and was listed as one of the top fifteen fugitives wanted by U.S. Marshals. Richard fled to Canada and eluded escape for over a year before finally being apprehended. He is now held at the ADX Florence supermax facility in Colorado.

John Dillinger Was A Career Criminal

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John Dillinger is one of the most famous prison escapees in American history. His lifestyle, arrest, and escape from prison were so mad that the events inspired the 2009 film Public Enemies starring Johnny Depp.

While the movie portrayed Dillinger as a suave crook and ladies man, in reality, he was a career criminal. He spent nine years in prison for robbery before being released in 1933. He was a free man for less than two months before robbing his first bank. He evaded the authorities until he was caught in Tucson, Arizona in January of 1934. Although the jail claimed to be “escape proof,” Dillinger proved that was false.

Dillinger’s demise wasn’t far off though…

John Dillinger’s Demise

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Before Dillinger was jailed in 1934, he was well-known for his gang involvement. By now his antics had cost ten men their lives, which made him one of the most wanted men in the country.

Just five weeks after his arrest, Dillinger, along with another inmate, used a fake gun carved out of wood and darkened with black shoe polish, to force the guards to let them out of jail. They took off in the Sheriff’s brand-new V-8 Ford to escape. The Sheriff, Lillian Holley, reportedly said, “If I ever see John Dillinger, I’ll shoot him dead with my own pistol.” The same year, FBI agents shot and killed Dillinger in Chicago.

The Ultimate Prison Break: Alcatraz

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Three convicts, Frank Lee Morris and brothers Clarence Anglin and John Anglin, escaped from Alcatraz (also called “The Rock”) in 1962. The outlaws left behind heads they made from bars of soap, toilet paper and real hair in their beds to make the prison guards think they were asleep. Meanwhile, each night they used crude tools to dig a tunnel that led to a service corridor.

The events at Alcatraz escape have become one of the most famous prison escapes of all time. Like Dillinger, a film was made back of the events called Escape from Alcatraz, starring Clint Eastwood.

The Ingenious Trio Was Never Seen Again

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After months of digging, Frank, Clarence, and John finally managed to break through a tunnel and escape via a corridor. From here, they climbed a ventilation shaft to reach the roof and escaped.

Alcatraz is on an island so the men made a raft from raincoats and emergency cement they stole from the prison supplies. They left the island around 10 p.m. and no one knew they were missing until the next day. It is believed they planned to make it to another nearby island, but they were never seen again. The FBI later determined they had likely drowned and also conceded that their escape plan was “ingenious.” Of course, many believe the trio survived and started life anew elsewhere.

Frank Forged A Career Out Of His Prison Escape

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Frank Abagnale got his start as a teenage con-man and became notorious for his acts. He also forged a future legal career out of his troubled past. Abagnale escaped from a Federal Detention Center in Atlanta, Georgia after convincing the guards that he was an inspector and not a prisoner.

A U.S. Marshall had forgotten his detention papers, so they believed him, and Abagnale was let go after several weeks of gaining their trust. Frank walked out of prison and was free for two months before he was caught in Washington D.C. He served his time in prison and was later paroled. Now, he advises the FBI on white-collar crime. In 2002, Steven Spielberg made a movie about his life starring Leonardo DiCaprio called Catch Me If You Can.

A School Shooter’s Failed Escape

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T.J. Lane gained notoriety for his disgusting display in a courtroom after he committed a school shooting at Chardon High School in 2012. He killed three classmates, and when facing the victim’s parents, he took off his jacket to reveal a shirt that said “Killer” and gave them the middle finger.

He was sentenced to three life sentences and later escaped from jail with two inmates, Lindsey Bruce and Clifford Opperud. The trio broke out of a medium-security prison in Ohio by using a homemade ladder to scale the prison wall. They made the ladder out of materials they found in a warehouse they gained entry into. They later escaped on foot but were all caught within hours of their escape.

The Texas Seven’s Crime Spree

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In December 2000, seven inmates (known as the Texas Seven) escaped from the maximum-security prison, John B. Connally Unit in Kenedy, Texas. Led by 30-year-old George Rivas, most of the men were already serving life sentences for crimes ranging from kidnapping to murder.

The men overpowered guards and locked them in a closet, and the Texas Seven were on their way to a new crime spree. They committed various crimes across Texas and into Colorado. In Irving, near Dallas, they killed 29-year-old police officer Aubrey Hawkins. The men eluded police for over a month before being featured on America’s Most Wanted. One of the men, Larry James Harper, killed himself rather than be taken into custody. Three of the remaining men have since been executed.

Choi Gap-bok Escaped Through A Food Slot

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Choi Gap-bok managed to slide through the tiny food slot at the bottom of the jail cell door. Yes, the tiny rectangular slot!

Most of these slots measure 6 inches tall and about 17 inches wide. To make matters even crazier, Choi was 50 years old when he escaped. He was in and out of jail in South Korea for the majority of his life where he picked up yoga. He had asked guards for skin ointment which he used to oil himself up enough to get out. The stunt has since been recreated, and it works if you are on the smaller side as Choi himself was 5’4”. Choi claimed he wanted to escape to prove his innocence and was caught six days later.

The Extremely Creative Parkhurst Escapees

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Had Andrew Rodger, Keith Rose, and Matthew Williams chosen a different path in life, they could have had some pretty successful careers in tool making. The three men escaped from the Parkhurst Prison (above) in the UK in 1995.

The trio made a 25-foot-long steel ladder which they used to scale the fence. They also made a working gun in the metal shop and a key which could unlock every door and gate in prison. Officials believe they were able to do so from memory by seeing a guard’s key. The three men were able to simply walk out of this prison. Their freedom was short-lived, and they were apprehended four days later.

These Jewish Prisoners Overtook A Nazi Death Camp

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This one is different than the rest, in a good way. Sobibor was a concentration camp during WWII, and the Nazi guards notoriously handled uprisings in horrifying ways. Some of the prisoners, including Leon Feldhendler and Russian First Lieutenant Alexander “Sasha” Pechersky, began to plan to fight back.

They planned to have every prisoner stage a fight at once. At this particular camp, the Nazi SS officers were in charge, but the guards were Ukrainians local to the area. Perchersky hoped that if they killed all of the SS soldiers, the Ukrainians would give up. The prisoners fashioned themselves various weapons to use. When the moment came, they were successful and killed every SS officer. Three hundred of the 600 prisoners escaped.

Richard Matt’s Lifelong Escape Techniques

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In 2015, Richard Matt made headlines after he escaped from Clinton Correctional facility alongside fellow prisoner David Sweat. This was not Matt’s first time as he had been escaping from various facilities since he was thirteen years old. In 1986, he fled the Erie County Correctional Facility, alluding police for four days. In 2007, he was imprisoned in Mexico and almost escaped but was shot down.

Matt’s son commented “He’s been shot like nine times. It’s like they can’t kill him.” He was sent back to the U.S. where he was tried for murder. This would be his last escape attempt. As he and Sweat managed to tunnel their way out of prison that landed them 500 feet outside of the prison wall. Twenty days after his escape Matt was shot and killed by officers. Sweat briefly escaped but was also apprehended only days later.

Shawshank Redemption, “El Chapo” Style

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Cartel leader, Joaquín Guzmán Loera, also known as “El Chapo” has become somewhat of a living legend for his multiple escapes. While he leads the notoriously violent Sinaloa cartel, some in Mexico view him as a Robin Hood-esque figure.

In 2015, El Chapo staged his most extraordinary escape from the maximum-security prison, Federal Social Readaptation Center No. 1. He had help from the outside for what unfolded next. Thirty-three feet deep in the ground lay a tunnel equipped with lights and air ducts, surely made by skilled construction workers. The tunnel ended nearly a mile away in a shower in an under-construction house. He was caught around six months later and has since been extradited to the United States.

This Frenchman Staged Three Helicopter Hijackings

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Frenchman Pascal Payet had been in and out of prison for over a decade before he was involved in an armored car heist in 1999 that ended with the death of a guard. He was imprisoned in the village of Luynes but fled in 2001 by high jacking a helicopter, although he was captured one week later.

In 2003, he pulled off a similar helicopter escape with three other prisoners. By 2007, he was one of the most closely-monitored prisoners due to his many escapes. Those measures didn’t work, and in July of 2007, four masked men hijacked a helicopter in Cannes and freed Payet from solitary confinement. He was captured several months later in Spain and was transferred back to French custody. His location has now since been kept private due to “security reasons.”

Willie Sutton Escaped Prison Four Times

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Willie Sutton was a career criminal although it was part of his “moral code” to never kill or hurt anyone. Willie was closely aligned with various Mafia members who were known to protect him whenever he was incarcerated. Bank and jewelry store robber, Mafioso Donald Frankos, even said that Willie made Jesse James and John Dillinger seemed like “amateurs.”

He escaped four times over his life. He used various methods that included a smuggled gun and dressing as prison guards. His last escape came in 1947 and he was recaptured in 1952 by an amateur sleuth named Arnold Schuster. Arnold was later killed in retribution by the mob for being a snitch. Willie was sentenced to 30 years in Attica State Prison but had his sentence reduced for good behavior and because his health was declining.

The O.G. Of Prison Escapes

Jack Sheppard

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Jack Sheppard was a small-time thief in 18th century London, who was renowned for his insane escapes. He became so well known that at each of his trials, people showed up hoping for some kind of fantastic display. One of his acts involved breaking through the ceiling of his cell and dropping a rope made of sheets down, which he pulled off two separate times.

The next time, guards restrained him with his legs stuck in irons cast to the floor with extra chains. However, Sheppard managed to fashion a lockpick out of a nail and used an iron bar from the chimney to break through the ceiling. He again managed to escape. Ultimately, Sheppard died when he was sentenced to death by public hanging – which was said to have been attended by a third of London’s population.