In 2005, he succeeded to escape by hiding in a container, with the complicity of workers from the waste collection services. On 13 December 2014 he escaped for the 20th time through the window by rope, after having sawed the bars.

Escaped Prison 22 times.

http://www.thelocal.dk/20141222/danish-escape-artist-caught-with-drugs-and-hooker

Joseph Bolitho Johns (c. 1826 – 13 August 1900), better known as Moondyne Joe, was Western Australia's best known bushranger. Born into poor and relatively difficult circumstances, he became something of a petty criminal and robber with a strong sense of self-determination. He is well remembered as a person who had escaped multiple times from prison.

Escaped from prison 5 times.

https://en.wikipedia.org/wiki/Moondyne_Joe

Yoshie Shiratori (?? ?? Shiratori Yoshie?, July 31, 1907 - February 24, 1979) was a Japanese national born in Aomori Prefecture. He had one daughter. He is best known for having escaped from prison four times. In total he was sentenced to life plus 23 years for his crimes but only served 26 years and was paroled in 1961.

In 1933 he was apprehended on suspicion of a murder and robbery he had allegedly committed with some accomplices. Prosecutors sought the death sentence but he escaped from Aomori prison in 1936 after using a length of wire to pick the lock on his handcuffs. He was soon recaptured and sentenced to life imprisonment. He escaped from Akita prison in 1942 by fleeing through an air vent in the prison's ceiling. After he was rearrested again three years were added to his sentence and he was incarcerated in Abashiri Prison. In 1944 he weakened his handcuffs and the inspection hole on his cell door by rusting them with miso soup and escaped. After World War II, he injured a man and the man later died. He was arrested again in 1946. Sapporo District Court sentenced him to death but in 1947, while awaiting execution in Sapporo Prison, he escaped by sawing through the floorboards of his cell with a sharpened piece of sheet metal then digging his way to freedom with a bowl.

Finally, in 1948 at the age of 41, Shiratori was exhausted and after receiving a cigarette from a police officer admitted that he was an escaped convict. The high court dismissed the murder allegation and revoked his death sentence instead sentencing him to 20-years in prison. He stayed in jail after that until he was paroled in 1961. He went to Aomori Prefecture in 1973 and he met with his daughter but he did not speak to her. He died of a heart attack in 1979. His ashes were taken by a woman who had cared for him.

Shiratori became an anti-hero. Akira Yoshimura published a novel Hagoku based on him. His memorial is in the Abashiri prison museum.[1] His family name Shiratori means swan in Japanese.

Escaped from prison 4 times.

https://en.wikipedia.org/wiki/Yoshie_Shiratori

Jack Sheppard (4 March 1702 – 16 November 1724) was a notorious English thief and gaol-breaker of early 18th-century London. Born into a poor family, he was apprenticed as a carpenter but took to theft and burglary in 1723, with little more than a year of his training to complete. He was arrested and imprisoned five times in 1724 but escaped four times from prison, making him a notorious public figure, and wildly popular with the poorer classes. Ultimately, he was caught, convicted, and hanged at Tyburn, ending his brief criminal career after less than two years. The inability of the notorious "Thief-Taker General" Jonathan Wild to control Sheppard, and injuries suffered by Wild at the hands of Sheppard's colleague, Joseph "Blueskin" Blake, led to Wild's downfall.

Sheppard was as renowned for his attempts to escape from prison as he was for his crimes. An autobiographical "Narrative", thought to have been ghostwritten by Daniel Defoe, was sold at his execution,[1] quickly followed by popular plays. The character of Macheath in John Gay's The Beggar's Opera (1728) was based on Sheppard, keeping him in the limelight for over 100 years. He returned to the public consciousness around 1840, when William Harrison Ainsworth wrote a novel entitled Jack Sheppard, with illustrations by George Cruikshank. The popularity of his tale, and the fear that others would be drawn to emulate his behaviour, led the authorities to refuse to license any plays in London with "Jack Sheppard" in the title for forty years.

Escaped prison 4 times.

https://en.wikipedia.org/wiki/Jack_Sheppard

Steven Jay Russell (born September 14, 1957) is a U.S. con artist known for escaping from prison multiple times. A film about his life and crimes was produced in 2009, named I Love You Phillip Morris. In 2011, his crimes were featured on the TV show I Almost Got Away with It in the episode "Got a Boyfriend to Support." A documentary about his crimes was aired on TV in 2005 On The Run episode "King of Cons" on Discovery Channel.

Escaped from prison 4 times.

https://en.wikipedia.org/wiki/Steven_Jay_Russell

Richard William Matt (June 25, 1966 – June 26, 2015)[1][2] was an American convicted felon known for several prison escapes, most notably the 2015 Clinton Correctional Facility escape.

Escaped prison 2 times.

https://en.wikipedia.org/wiki/Richard_Matt

John Herbert Dillinger (/d?l?nd??r/; June 22, 1903 – July 22, 1934) was a infamous American gangster in the Depression-era United States, who operated with a group of men known by some as the Dillinger Gang or Terror Gang that were, among other activities, accused of robbing 24 banks and four police stations. Dillinger escaped from jail twice. He was also charged with, but never convicted of, the murder of an East Chicago, Indiana police officer who shot Dillinger in his bullet-proof vest during a shootout, prompting him to return fire. It was Dillinger's only homicide charge.

In the heyday of the Depression-era outlaw (1933–1934) Dillinger was the most notorious of all, standing out even among more violent criminals such as Baby Face Nelson, Pretty Boy Floyd, and Bonnie and Clyde, as evidenced by the fact that decades later, the first major book about 1930s gangsters was titled The Dillinger Days. He courted publicity, styling himself as a Robin Hood figure, and the media of his time ran exaggerated accounts of his bravado and colorful personality, causing the government to demand federal action, and J. Edgar Hoover developed a more sophisticated Federal Bureau of Investigation as a weapon against organized crime, using Dillinger and his gang as his campaign platform.[1]

After evading police in four states for almost a year, Dillinger was wounded and returned to his father's home to recover. He returned to Chicago in July 1934 and met his end at the hands of police and federal agents who were informed of his whereabouts by Ana Cump?na? (the owner of the brothel where Dillinger sought refuge at the time). On July 22, 1934 the police and Division of Investigation[2] closed in on the Biograph Theater. Federal agents, led by Melvin Purvis and Samuel P. Cowley, moved to arrest Dillinger as he exited the theater. He pulled a weapon and attempted to flee but was shot four times and killed.

Escaped prison 2 times.

https://en.wikipedia.org/wiki/John_Dillinger

Pascal Payet (born 7 July 1963) is a French criminal who has gained notoriety for his daring prison escapes using hijacked helicopters. He was initially sentenced to a 30-year jail term for a murder committed during the robbery of a security van in 1997.

Escaped prison 2 times.

https://en.wikipedia.org/wiki/Pascal_Payet

William Francis "Willie" Sutton, Jr. (June 30, 1901 – November 2, 1980) was a prolific American bank robber. During his forty-year criminal career he stole an estimated $2 million, and eventually spent more than half of his adult life in prison and escaped three times. For his talent at executing robberies in disguises, he gained two nicknames, "Willie the Actor" and "Slick Willie." Sutton is also known as the namesake of Sutton's law, though he denied originating it.

Escaped from prison 3 times.

https://en.wikipedia.org/wiki/Willie_Sutton

Richard Lee McNair (born December 19, 1958) is a convicted murderer known for his ability to escape and elude capture. In 1987, McNair murdered one man and shot a second man four times during a botched robbery. He is currently serving two terms of life imprisonment for these crimes.

After McNair's arrest, he escaped three times from three different institutions using various creative methods. On his first attempt he used lip balm to squeeze out of a pair of handcuffs. He escaped a second time by crawling through a ventilation duct. In his last escape from a federal prison in April 2006, he mailed himself out of prison in a crate.[1] This resulted in his mugshot being featured a dozen times on the TV show America's Most Wanted, and made him one of the top fifteen fugitives wanted by US Marshals. McNair traveled to Canada twice in order to evade capture, traveling across the country for over a year before being apprehended in a random police check. Much of what the public knows about McNair's escape and his time as a fugitive is through McNair's prison correspondence with a Canadian journalist, Byron Christopher.

Escaped from prison 3 times

https://en.wikipedia.org/wiki/Richard_Lee_McNair

Alfred George "Alfie" Hinds (1917 – 5 January 1991) was a British criminal who, while serving a 12-year prison sentence for robbery, broke out of three high security prisons. Despite the dismissal of thirteen of his appeals to higher courts, he was eventually able to gain a pardon using his knowledge of the British legal system.

Escaped from prison 3 times.

https://en.wikipedia.org/wiki/Alfred_George_Hinds