Top Ten Prison Breaks Of All Time - Oxford Castle & Prison (2023)

Prison escapes may be rare, but when they do occur, they often cause scandal and attract a lot of media attention. We've compiled the top 10 prison escapes of all time, all true stories with fascinating results. To enjoy!

10: Yoshie-Shiratori

Yoshie Shiratori is best known for breaking out of prison four times in three years. After his murder conviction, he was sentenced to life in prison plus 23 years in prison.

Shiratori escaped from Aomori Prison in 1936, was recaptured, and escaped from Akita Prison in 1942. In 1944, he rusted his handcuffs and an inspection hole with miso soup before escaping from Abashiri Prison. In 1946 he was caught again. The Sapporo District Court sentenced him to death, causing Shiratori to desperately find an escape route, and in 1947, he dug a tunnel and escaped for the fourth time!

In 1948, he was rearrested after admitting to a police officer that he was a fugitive. His death sentence was overturned, and Shiratori ended up serving 26 years before being paroled in 1961.

9. John Dillinger

John Herbert Dillinger Jr. was a Depression-era bank robber who robbed two dozen banks and four police stations during his crime spree.

He has escaped prison twice in his criminal career. During a stint in an Indiana prison, Dillinger befriended several experienced bank robbers who taught him how to be a successful criminal. After being released at the height of the Great Depression, Dillinger immediately returned to crime.

After robbing two banks, he was captured and imprisoned in Lima in the fall of 1933. Dillinger used his time in prison to help escape a group of inmates he had met during his previous incarceration. Prisoners smuggled weapons into their cells, which they escaped just four days after Dillinger's arrest. The group then returned to the prison, posing as Indiana State Penitentiary officers, and successfully freed Dillinger from his cell.

After another series of bank robberies, Dillinger was recaptured in 1934 and sent to Crown Point Prison. The police boasted to the media that the prison was escape-proof. This was proven completely wrong when Dillinger made a fake pistol out of a piece of wood, allegedly using shelves in his cell and a razor to carve it. Dillinger tricked a guard into opening his cell and then took seventeen men hostage before luring the guards back to the cell block and locking them in his own cell. So he ran away.

Dillinger evaded police across four states before meeting his end on July 22, 1934, when a lead led to a shooting in Chicago. Dillinger was shot three times and pronounced dead shortly thereafter.

8. Alfred George Hinds

Alfred George Hinds was a British criminal who successfully escaped from three maximum security prisons while serving a 12-year sentence. Hinds' first escape was from a Nottingham prison in 1958, where he managed to escape through locked doors and a 20-foot prison wall to his freedom. This performance earned him the nickname "Houdini Hinds" in the media.

During his escape, he traveled across Europe and worked as a painter-decorator before being arrested after 248 days at liberty.
Hinds used his new arrest to his advantage, filing a lawsuit against the authorities and thus finding reasons to be escorted to court.

Accomplices provided Hinds with a padlock and attached bolt catches to a toilet, then, as Hinds was being escorted to the toilet, Hinds bundled the two guards into the toilet and locked them. Hinds fled to Fleet Street and went to the airport, where he was captured five hours later.

Hind's third and final prison break came less than a year later, when he escaped from Chelmsford Prison. He fled to Ireland, where he lived under an assumed name for two years before being arrested for driving an unregistered car and rearrested. After his eventual release from Parkhurst Prison, Hinds became a member of Mensa.

7. John Gerhard

John Gerard is the only person known to have escaped the infamous Tower of London. Gerard, a Jesuit priest, was arrested for continuing to preach his Catholic faith when the Church was under severe persecution in Elizabethan England.

During his detention, he underwent numerous interrogations and was often tortured for information. He never broke down, but was eventually sentenced to death for his "crimes". Desperate to escape, Gerard communicated with allies outside through smuggled notes written in invisible orange juice ink.

These allies rowed a boat into the tower's moat and Gerard managed to escape using a rope thrown to him. After nearly falling from his sore hands, Gerard escaped death by boarding his boat, fleeing England and spending the rest of his life in Rome.

6. Texas Seven

A group of prisoners known as the Texas Seven escaped from the John B. Connally Unit on December 13, 2000. An elaborate scheme devised by the group resulted in the overpowering and restraining of 16 people, including supervisors, officers and three inmates bystanders.

After the coup, the victims' clothes, credit cards, and identity cards were confiscated and used to impersonate civilians at the prison's back gate. Four of the perpetrators stayed behind to call the prison tower guards to distract them. The rest ambushed the watchtower and stole several weapons and then stole a prison maintenance truck in which all seven of them left the prison.

They were arrested just over a month later. Six of the seven were sent to death row in Texas, while the seventh (Larry James Harper) committed suicide rather than return to prison.

5. The Escape of the Empress Matilda

In the autumn of 1142, the Empress Matilda was besieged at Oxford Castle by soldiers loyal to her cousin Stephen. Across the country, a battle dubbed "The Anarchy" was raging for the crown of England.

Stephen, grandson of William the Conqueror and cousin of Matilda, claimed the crown and took turns laying siege to each other's strongholds. The siege of Oxford Castle lasted three months.

Matilda's epic escape took place on a freezing, snowy December night when, legend has it, she wrapped herself in a white cloak and fled across the ice to Wallingford Castle on makeshift skates. A truce was agreed to end the battle, with Matilda agreeing that Stephen could keep the throne as long as his son Henry became his heir.

I suspect Stephen died not long after this agreement was forged, allowing King Henry II to ascend the throne. You can find out more about the Empress Matilda and other amazing stories atFacebook,Instagramit is oursthe blog!

4. Escape from Alcatraz

In June 1962, three prisoners escaped the infamous Alcatraz Island and mysteriously disappeared. A plan devised by fellow prisoner Allen West saw Frank Morris, John Anglin and their brother Clarence spend two years digging an escape route through cell walls and building a raft to sail to freedom.

The mannequins were placed in the beds of the three prisoners to trick the prison guards into not discovering they were gone until the next morning.

Parts of the raft and lifebuoys were later found in the bay along with some of the prisoners' personal belongings, leading investigators to conclude that the men had drowned.

The FBI officially closed the case on December 31, 1979, concluding that "no credible evidence has emerged that the men were still alive". However, no bodies were discovered.

3. Ronnie Biggs

Ronald Arthur Biggs, better known as Ronnie Biggs, is known for his role in the Great Train Robbery of 1963 and for being a fugitive for 36 years until his voluntary "surrender" in 2001.

Biggs was originally captured and imprisoned for his involvement in the Great Train Robbery. He served just 19 months of his sentence before escaping Wandsworth Prison on July 8, 1965 by scaling a wall with a rope ladder and getting into a waiting van.

He fled by boat to Brussels and then to Paris, where he adopted a new identity and underwent cosmetic surgery. He spent most of his 36 years on the run in Australia and Brazil. On 7 May 2001 Ronnie voluntarily returned to the UK and was promptly arrested and jailed. He spent 8 years in prison before being released on bail in 2009. He died in December 2013.

2. Labyrinth Prison

HM Prison Maze was the scene of the biggest prison break in British history when, on 25 September 1983, 38 IRA prisoners broke out of the maximum security prison, widely regarded as one of the best escape-proof prisons in Europe.

Fifteen-foot-high fences and concrete walls topped with five-and-a-half-meter-thick barbed wire surrounded Block H, and solid steel doors barred all exits from the prison complex.

The prisoners had been planning their escape for several months. Two accomplices, Bobby Storey and Gerry Kelly, began working as orderlies to identify weaknesses in the system, and six handguns were smuggled into the prison using these raids. Shortly after 2:30 pm, the inmates took over, simultaneously holding the correctional officers hostage and hijacking a truck delivering food to the block.

Concierge staff were also taken hostage and after several attempts the main gate was opened. After two cars blocked the makeshift road directly in front of the prison, the inmates got out of the truck and escaped over a fence. The prison was closed at 4:18 pm minus 38 prisoners. Twenty correctional officers were injured and one died after suffering a heart attack during the escape.

1. The Great Escape

The "Great Escape" from the Stalag Luft III POW camp planned by Squadron Leader Roger Bushell in the spring of 1943 took place on the night of 24 March 1944.

Bushell commanded the Escape Committee at the North Compound, where the British airmen were billeted. His "Great Escape" plan called for building three "very deep and long tunnels" under the camp fences. The tunnels were named Tom, Dick and Harry. If one of the tunnels was discovered by the Germans, it was assumed they would never suspect that two more might be in the works.

Over 600 prisoners were involved in building the tunnels, with Bushell attempting to free 200 prisoners. The tunnels were 30 feet below the surface and were only 2 feet square. The walls were reinforced with pieces of wood, most recovered from the inmates' beds.

Prisoners were very creative with their looted items. Cans became shovels and candlesticks; The candles were made from the fat of the soups served in the camp, while the wicks were made from old clothes. The sand excavated in the tunnels was discreetly scattered as the prisoners walked through the camp.

The 200 potential refugees were divided into two groups. The first group of 100, the so-called "serial offenders", were guaranteed places, including prisoners with a good knowledge of German or a history of escaping. 70 of the men were chosen because they are believed to have contributed the most to the tunnels. The second group was chosen by lot.

The escape attempt began on Friday, March 24th. At 22:30, the first man emerged and found that the tunnel was short. Instead of reaching a nearby forest, the tunnel exited just short of the tree line and dangerously close to a watchtower. Despite this, 76 men crawled through the tunnel to freedom before the 77th was spotted by guards at 4:55 am on 25 March.

Of the first 76 escapees, 73 were recaptured. As an example, Hitler orders the execution of half of the refugees.

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