8 of the Most Shocking Prison Breaks in History

Prisoners across history have devised surprising, often cinematic, escapes from the confines that hold them. Whether it be a 17th-century Robin Hood staging a series of folklore-inspiring prison breaks or a notorious drug lord tunnelling out of a maximum security federal prison, these escapees were willing to risk everything for their freedom. 

1. John Sheppard a.k.a. Honest Jack’s Daring Escapes 
2. John Dillinger’s Several Escapes
3. Rédoine Faïd’s Grand Prison Escapes
4. The 1983 Maze Prison Escape 
5. The 1962 Alcatraz Escape 
6. El Chapo’s Escapes
7. The 1864 Libby Prison Escape 
8. Ted Bundy 

John Sheppard a.k.a. Honest Jack’s Daring Escapes 

John Sheppard (later nicknamed Honest Jack on account of his popularity with the working class) was an infamous thief and petty criminal who escaped from London prisons an astounding four times in 1724. He was beloved for his charm, good looks, and the non-violent nature of his criminal activity; he was akin to a sort of Robin Hood of Georgian England. Sheppard’s spectacular escapes later made him the subject of countless works of art including an opera, multiple stage productions, and three feature films. 

Sheppard was a talented carpenter's apprentice under the tutelage of his mother’s employer, William Kneebone. After falling in with a crowd of criminals and beginning a romantic relationship with a local sex worker named Elizabeth Lyon, Sheppard began stealing to supplement his legitimate income. He engaged in some petty theft, then began stealing from homes where he was working as a carpenter. He quit his apprenticeship in August 1723.  

After Sheppard, Lyon, and Sheppard’s brother Tom were arrested for a burglary they had committed in early 1724, Sheppard was imprisoned in St. Giles’s Roundhouse before escaping within just a few hours; he broke through the ceiling of his cell and lowered himself to the ground with a rope fashioned from bedding. Just a few weeks later, Sheppard was arrested again, this time for pickpocketing, and detained at central London’s New Prison alongside Lyon. Within days, the two were able to file through their manacles and escape from their cell using a rope fashioned from bedsheets—much like Sheppard’s prior escape from St. Giles’s. 

Sheppard returned to his criminal activity before being arrested once more in July 1724 at the direction of local crime boss Jonathan Wild. He was sent to London’s Newgate Prison, convicted of theft on August 12, 1724, and sentenced to death. But just days before his scheduled September 4 execution, Sheppard loosened a bar on his cell’s window and slipped through the gap while Lyon and another accomplice distracted the prison’s guards. 

Sheppard was able to hide out for a few weeks before he was eventually arrested again on September 9, 1724, and sent back to Newgate Prison, this time with additional security measures in place. Despite the increased security, Sheppard was able to bust free again by slipping out of his handcuffs and sneaking out of the prison. He disguised himself as a beggar and returned to London—and was then arrested for a fifth and final time on November 1, 1724, after burgling a pawnbroker’s shop. 

Sheppard was again sentenced to death (and monitored around the clock by guards) and scheduled to be executed on November 16, 1724. After his final attempt at escape was foiled, Sheppard was hanged on November 16, 1724, before a crowd of nearly 200,000 Londoners. 

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John Dillinger’s Several Escapes

John Dillinger was a Depression-era crime boss responsible for a string of bank robberies across the Midwest; he was among one of the many gangsters the public valorized during the Great Depression. Dillinger landed in prison for the first time after he and criminal accomplice Ed Singleton were arrested for the robbery of a Mooresville, Indiana, grocery store in early September 1924. The pair only made off with $50 (roughly $937 today)—but Dillinger remained in prison until he was paroled in May 1933 after serving more than eight years of his 10- to 20-year sentence.

Dillinger returned to criminal activity within weeks of being granted parole. After committing two bank robberies in June and August 1933 (this time making off with $10,000—almost a quarter of a million dollars today), he was arrested in Dayton, Ohio, and sent to a Lima, Ohio, jail to await trial. Guards discovered Dillinger had a document outlining an escape plan with him, but he refused to confirm what it was. 

He formulated a plan for some of his criminal acquaintances to escape their confinement. The ragtag group of criminals, later known as “the First Dillinger Gang,” impersonated Indiana State Police officers in an attempt to free Dillinger under the pretense of his being extradited to Indiana. When Sheriff Jess Sarber requested the “officers” show their credentials, one of the fake police officers shot and killed him while the group escaped to Indiana with Dillinger in tow. 

Dillinger and his gang then embarked on a series of robberies before decamping to Tucson, Arizona, to hide out. Authorities were later able to locate and arrest Dillinger and his accomplices; Dillinger was sent back to Indiana to face trial for the murder of a police officer during one of the gang’s robberies. Though he was locked inside what was then described as an “inescapable” prison, the famed criminal was able to break out again in March 1934 by carving a fake gun from wood and using it to threaten prison guards. He then fled to Chicago.

A nationwide manhunt ensued following the breakout. Dillinger laid low with his girlfriend, Billie Frechette, and assembled a new gang. They pulled off robberies in South Dakota and Iowa within weeks of his escape. Following a shootout with authorities and a near arrest at a rural Wisconsin vacation lodge, Dillinger reentered hiding in Chicago and underwent cosmetic surgery to (unsuccessfully) alter his appearance in an effort to conceal his identity. 

Romanian madam Anna Sage later gave Dillinger’s location to authorities to save herself from deportation. On July 22, 1934, after catching a movie at Chicago’s Biograph Theater, Dillinger was ambushed by federal agents before being shot and killed while trying to escape down a nearby alley. Despite his criminal reputation, thousands attended his funeral. 

Rédoine Faïd’s Grand Prison Escapes

Rédoine Faïd is a career criminal known for his spectacular escapes from French prisons in 2013 and again in 2018. He’s the second youngest of 12 children born to Algerian immigrants in northern France; Faïd’s life of crime began when he was just a teen after joining his brothers in their criminal enterprise. Following a slew of armed robberies throughout the mid-1990s, he was arrested and spent the next decade in prison. He also published a memoir, Robber - From the Projects to Organized Crime, that chronicled his time in organized crime, prison stint, and purported reform. 

Despite having claimed to have left his life of crime behind, Faïd found himself back in prison in 2011. He had violated his parole and authorities suspected he had been involved in a deadly armed robbery that resulted in the death of a police officer. 

Faïd made a daring escape in 2013 thanks to his multiple accomplices, who snuck weapons and explosives into the prison. The group took multiple prison guards hostage and used the explosives to break through a series of security doors, clearing the way for Faïd’s escape. Faïd made his way to the getaway car that was waiting for him, fled the prison, and went into hiding. 

His freedom was short-lived. French authorities arrested him just weeks later, and Faïd was given an additional decade in prison for the escape on top of his already sizable sentence for his connection to the 2010 robbery. 

But that didn’t stop Faïd from breaking free again in 2018—this time using a helicopter. On July 1, 2018, a group of Faïd’s accomplices hijacked a chopper before flying it to the prison, which was located in the outskirts of Paris. They landed in the courtyard and deployed smoke bombs to shield themselves from guards while they used angle grinders to break through to the visitation room, where Faïd and his brother were waiting. The brothers boarded the helicopter and escaped, and a months-spanning manhunt ensued. 

He was finally arrested alongside his brother in October 2018, this time receiving an additional 14-year prison sentence for his cinematic escape. 

The 1983 Maze Prison Escape 

Better known by those with Irish republican sympathies as the Great Escape, the Maze Prison escape was a 1983 maximum security prison break orchestrated by the Irish Republican Army (IRA), a paramilitary group seeking to end British rule in Northern Ireland. The Maze Prison was said to be one of the most secure prisons in all of Europe; the big escape was one of many the IRA managed to pull off during the Troubles, a longstanding nationalist conflict between Irish and British forces spanning from the 1960s to late 1990s. 

IRA prisoners Bobby Storey and Gerry Kelly were able to facilitate the smuggling of six firearms into the prison to aid in their escape. The guns were distributed among fellow their IRA prisoners, who used the weapons to overpower the prison officers, take them hostage, and seize control of the H7 prison block. They then commandeered a food delivery truck at gunpoint and loaded nearly 40 prisoners into the vehicle to be smuggled out.  

When prison officers at the main gate stopped the truck, a fight between the guards and prisoners broke out, leading to the death of one officer and seriously injuring several others. Ultimately, 38 of the prisoners were able to make their way through the main gate and escape. Though 19 prisoners were recaptured within days, half of those who broke free were able to successfully decamp to Ireland, the United States, or mainland Europe. 

The ordeal was a huge embarrassment for the British government and became an indispensable piece of propaganda for the IRA in their campaign against the British occupation of Ireland.

The 1962 Alcatraz Escape 

On the evening of June 11, 1962, Clarence Englin, John Englin, and Frank Morris escaped from the notorious maximum security federal prison located on San Francisco Bay’s Alcatraz Island. They were well acquainted with one another through prior incarcerations. 

Morris, the Englin brothers, and fellow inmate Allen West began formulating their plan to break free in late 1961. Under Morris’s leadership, the gang spent months widening the opening in the ventilation ducts within their cells; they concealed their progress from guards using pieces of cardboard. Eventually, the men were able to slip into the ventilation ducts to access an empty floor of their cellblock, where they set up an ad hoc shipyard. 

They then assembled a raft using dozens of raincoats and other materials filched from across the prison (their creation was inspired by a design Morris had seen in an issue of Popular Mechanics). After placing cleverly assembled papier-mâché busts in their bunks to avoid detection by the guards, the group—with the exception of West, whose cell ventilation opening hardened, stopping his escape—convened on the prison’s roof before shimmying down a ventilation pipe, hopping a barbed wire fence, and setting sail on their improvised raft from the island’s northeast shore. They boarded the raft sometime around 10 p.m. on June 11, 1962, and set sail for Angel Island. But the trio was never seen again.

The group’s absence was not discovered until the following morning, by which time they were long gone. The FBI launched an investigation and authorities deemed the men almost certainly drowned. That didn’t stop the ordeal from becoming the subject of widespread conspiracy theories and speculation in the years to come. Alcatraz was officially closed as a federal penitentiary less than a year later, though it still remains open today as a museum and macabre tourist attraction. 

El Chapo’s Escapes

Joaquín Guzmán, better known as El Chapo (a Spanish nickname meaning “shorty”), is an internationally notorious drug lord said to be responsible for the deaths of thousands while heading the Sinaloa Cartel, one of the largest global criminal enterprises. He’s currently serving a life sentence in ADX Florence, a federal maximum security prison in the Colorado Rockies. But before that, El Chapo managed two daring escapes from prison before his final arrest in 2016. 

He pulled off his first escape in 2001 while serving a 20-year sentence in a maximum security prison near Guadalajara, Mexico. Though he’s said to have enjoyed an incredibly luxurious lifestyle while incarcerated in Mexico, his escape was prompted by a looming extradition to the United States on money laundering charges. El Chapo bribed dozens of the prison’s staff and was successfully smuggled out of the facility in a laundry cart. He then spent more than 13 years on the lam. 

After more than a decade of murder and marauding, El Chapo was arrested again in 2014 at a beachfront hotel with his family. He was indicted on drug trafficking charges in Mexico, but was able to delay his extradition to the United States by filing numerous injunctions. He escaped incarceration once more while awaiting trial via a tunnel that led from the shower of his cell to a staged construction site nearly a mile away. When authorities finally discovered the tunnel, they found a meticulously constructed escape route complete with a complex ventilation system and modified railway to transport tools and earth. 

The drug kingpin was caught again after he was arrested following a shootout with authorities on January 8, 2016. He spent another year in a Mexican prison before finally being extradited to the United States in early 2017. Following a months-long trial in New York, El Chapo was convicted of more than a dozen charges including murder, money laundering, and drug trafficking; he was given a lifelong prison sentence. 

The 1864 Libby Prison Escape 

Confederate forces had seized the facilities that would become Libby Prison—once a locally owned ship chandler—early in the Civil War and converted it into what was thought to be an “escape proof” prison. But they couldn’t stop the 100 Union soldiers who banded together to break free.

The Union soldiers slowly dug a passage from the prison’s first floor to its basement, where they were then able to enter an area of the building nicknamed “Rat Hell.” Slipping into Rat Hell allowed them to avoid detection by Confederate guards while they worked for more than two weeks to burrow a tunnel from the basement into a shed on the grounds of an unoccupied lot across the street. 

On the evening of February 9, 1864, more than 100 Union prisoners fled through the tunnel before the Confederate soldiers became aware of their absence at the following morning’s headcount. Nearly half of the escaped soldiers were successfully recaptured, with just 59 making it to Union territory successfully. 

Ted Bundy 

Serial killer Ted Bundy was arrested in August 1976 for possession of burglary tools after an officer spotted his vehicle cruising a Salt Lake City suburb in the early hours of the morning. Following his arrest, authorities began connecting Bundy to numerous unsolved murder cases across the western United States. 

Bundy opted to serve as his own counsel while on trial for the murder of Caryn Campbell in 1977; he was subsequently granted access to the courthouse’s law library without handcuffs or leg shackles. While visiting the library, he slipped his inattentive guards and leapt out of the library’s second-story window. Bundy spent six days on the lam before authorities recaptured him. 

Once back in prison, he wasted no time trying to hatch another plan to escape. Bundy lost a considerable amount of weight and slipped through a hole he had carved in his cell’s ceiling using a hacksaw. On December 30, 1977, he climbed through the hole and, via the ducts in the ceiling, made his way into a jailer’s apartment before donning civilian clothing and simply walking out of the prison. He ultimately made his way to Florida, where he’d claim the lives of his last known victims. He was arrested in the Sunshine State after more than a month on the run. 

Bundy was found guilty of all three of the murders he’d committed in Florida. He spent just under a decade on death row before his execution on January 24, 1989.