6 Joel Kaplan escaped a Mexican prison without breaking a single law in 1971. This is because breaking out of jail in Mexico is only illegal when violence is used against prison officers or any property. The helicopter used for the escape was privately owned, and it followed every FAA standard. Also, after reaching Texas, Kaplan and the pilot used their real names which made the case completely non-criminal. 

Kaplan was a businessman and belonged to a wealthy family. He was charged for his business partner’s, Louis Vidal Jr.’s, murder in Mexico City in 1962. Along with Joel, a prison inmate, Carlos Antonio, also fled with him out of the prison.

A helicopter came to receive them at the prison, and it dropped them on a private plane at a nearby airport. The plane in turn delivered them to the Texas border where the two inmates separated. Kaplan headed for California, and Antonio for Venezuela.

The escape was completely legal since no person or any property was harmed or damaged while escaping the prison, and no prisoner or official was involved. The helicopter and also the plane was privately owned, so one cannot claim that they were used inappropriately.

Everything during the flight was also carried out according to FAA standards, and when they reached Texas, the pilot and Joel used their real names while speaking to the customs officials.

Later, no further extradition proceedings were initiated against Kaplan or Antonio. (source)

7 Joseph Bolitho Johns, also known as “Moondyne Joe,” escaped prison so many times that a special “escape-proof” jail had to be built for him. The Governor claimed that if he escaped this one, he’d forgive him. Joe took the challenge and escaped from the special prison, too. He was caught again a couple of years later, but the Governor kept his word and freed him. 

Joseph has a long history of committing crimes, getting caught, escaping prison, and getting caught again. He had committed big and small crimes such as burglary and stealing, killing and eating a neighbor’s ox, possessing a firearm, etc.

Joseph was caught with his gang in present-day Westonia, and police were more than ever determined to not let him escape this time. He was sentenced to five years of hard labor and was kept in an “escape-proof” cell which was specially made for him.

The governor of the Swan River Colon, Hampton, challenged Moondyne by stating, “If you escape once again, I will forgive you,” and he sounded pretty confident in his voice. Joe took the challenge, and on 7 March 1867, he escaped from a hole that he had made in the wall and disappeared through an unlocked side door of the prison.

The police didn’t manage to find him immediately, but he was caught after two years when he was stealing wine. He was sentenced to prison for four years, but the governor kept his word and freed him in 1871. Joe continued involving himself in criminal activities and escaping prisons even after he got married and was 70 years old. (1, 2)

8 The drug lord Joaquin “El Chapo” Guzman escaped prison in a dirty laundry basket in 2001. He spent 2.5 million dollars to bribe 70 guards in total, which included the director of the prison himself. 

When Guzman made his way out of the prison, he was in confinement for murder and drug trafficking. He was caught in Guatemala in 1993 and was sentenced to 20 years of confinement. Drug trafficking was still active under his name even when he was behind the bars.

In January 2001, he escaped the maximum-security prison in a basket of dirty laundry. He was only able to move out because he had bribed 70 prison guards along with the prison director to help him get out of the prison. He spent a total of 2.5 million dollars for that bribe.

For the next 13 years, he disappeared, and his drug empire grew so large that it became the full quarter of the traffic of illegal narcotics headed to the US. The city of Chicago recognizing him as Public Enemy Number 1 in 2013. He was the first gangster to be named such after Al Capone in the 1920s. (1, 2)

9 In 1995, a convicted killer named Daniel Heiss observed that the key designed on the cover of the prisoner’s information handbook was the master key to all locks. Soon his inmate, Shane Baker, a jeweler, replicated the key, and both the murderers escaped the prison. 

Daniel Heiss was inside the territory prison of Berrimah Jail In Darwin for committing murder. A booklet was given to all the prisoners at the jail which had a key design that a former jail officer confirmed was of the master key that opens all the cells In Berrimah Jail.

A former prison officer mentioned that the design on the cover page of the handbook was of the master key and was very easy to replicate. “It was just an E-shaped design,” he said.

Shane Baker, another prison inmate, was a jeweler and was convicted for murder as well. He had jewelry-making equipment in his cell, and he used them to make the key.

Shane was unable to reach his arm to the lock, but Daniel did, so Shane used to pass the key to Daniel to suggest changes in the shape of the key required. The key finally fitted the lock one day, and both the criminals ran away through razor-wire perimeter fences.

Shane was captured within a few days, but Daniel disappeared. Officials carried out a 12-day manhunt but called it off since there were no hopes left.

A prison officer said that Heiss left a message on the prison wall which read “The bird has flown,” and his escape was a huge embarrassment for the authorities. The handbooks were immediately confiscated, and new locks were installed in the cells. (source)

10 Yoshie Shiratori was an anti-hero in Japan for his four famous prison escapes. The first time he picked the locks with metal wire, the second time he climbed up to the ceiling of the prison and broke out of a skylight, next time he dislocated his joints to escape through a small food slot, and lastly he dug a tunnel with bowls to escape.

Yoshie Shiratori was famous all over Japan for his crazy prison escapes and was considered an anti-hero in Japanese culture.

The first prison break was quite simple in comparison to the other ones. In 1936, he escaped the Aomori Prison by studying the guard’s routine for months and picked the lock of his cell with the help of a metal wire found in the bucket for bathing.

Just after three days, he was captured again while he was stealing supplies from a hospital. He was sentenced to prison for life this time and was transferred to Akita Prison in 1942. This time, he climbed the prison wall every night to loosen the vent leading outside and finally exited through the skylight.

After running away, he went to one of the guards, Kobayashi’s, house, seeking some help since he considered him to be very kind and respectful. As soon as he went to the bathroom, the guard called out for police, and Shiratori was recaptured.

The third time he escaped from the Abashiri Prison, Northern Hokkaido. He poured miso soup on his handcuffs so they would rust and break off, which they did. Then he dislocated both of his shoulders to move out from his cell through the tiny food slot. Shiratori’s efforts didn’t last for very long and he was captured again shortly.

This time he was sentenced to death and was kept in Sapporo Jail. From there, he escaped in 1947 after digging a tunnel in the floor by just using miso soup bowls. He used to place the dirt in a small pocket below the floorboards.

He was again captured by a guard after several years and spent 14 years in Fuchu Prison, Tokyo. After that, he lived with his daughter for a decade doing odd jobs in Aomori and finally died because of a heart attack in 1979, aged 71. (source)