The following is a list of historically infamous prison escapes, and of people who escaped multiple times:
Famous historical escapes
There have been many infamous escapes from prison throughout history:
13th century In 1244, whilst imprisoned in the Tower of London, Gruffydd ap Llywelyn Fawr crafted a makeshift rope made of bed sheets and cloths, lowered it, and climbed down. However, due to his weight, the rope broke and he fell to his death.
16th century
Dirk Willems (also spelled Durk Willems; died 16 May 1569) was a Dutch Anabaptist martyr most famous for escaping from prison but then turning back to rescue his pursuer – who had fallen through thin ice while chasing Willems – only to be recaptured, tortured, and killed (burned at the stake) for his beliefs.
17th century In 1621, Dutch author Hugo de Groot escaped from Loevestein Castle, where he was held captive, by hiding himself inside a book chest. He was then smuggled outside.
18th century The French priest Abbé Bucquoy escaped from For-l'Évêque in 1705 and from the Bastille in 1709. Englishman Jack Sheppard took to theft and burglary in 1723, and was arrested and imprisoned five times in 1724 but escaped four times, making him a notorious public figure and wildly popular with the poorer classes. The Italian author and adventurer Giacomo Casanova escaped from prison in 1757. In 1781, Samuel Smedley was imprisoned in Old Mill Prison in Portsmouth, England. Smedley eventually escaped. Eugène-François Vidocq a French criminal turned criminalist, and considered to be the father of modern criminology and of the French national police force, escaped multiple times in 1795 – 1796 over the course of a few weeks at the age of 20 while in captivity with the help of Francine, but was always captured soon again. He is also regarded as the first private detective. The former criminal became the founder and first director of France's first criminal investigative agency, the Sûreté Nationale, as well as the head of the first known private detective agency.
19th century
On 27 November 1863, Confederate general John Hunt Morgan and six of his officers, most notably Thomas Hines, escaped from their cells in the Ohio Penitentiary by digging a tunnel from Hines' cell into the inner yard and then ascending a wall with a rope made from bunk coverlets and a bent poker iron. In the Libby Prison escape, during the American Civil War, over 109 Union POWs broke out of a building at Libby Prison in Richmond, Virginia, on the night between 9 and 10 February 1864. Fifty-nine of the 109 prisoners successfully made it back to the Union lines; two were drowned in the nearby James River, and 48 were recaptured. Anarchist activist Peter Kropotkin managed to escape from a low-security prison in Saint Petersburg. He hid himself in one of the finest restaurants there and later moved to England. The notorious outlaw Billy the Kid managed to escape from prison in 1881, but was captured and shot by Pat Garrett only a few months later. Italian brigand Giuseppe Musolino escaped from prison in 1899, subsequently going on a killing spree targeted against those who testified against him at his first trial. He was recaptured in 1901.
1900–1949 In 1901, Lum You was convicted of murder and sentenced to death by a Pacific County, Washington, court. He enjoyed great public sympathy, including from county officials, who supposedly allowed him to escape by leaving his cell door unlocked at night. He eventually seized the opportunity, but within a few days he either gave himself up or was recaptured. German Naval Air Service Kapitänleutnant Gunther Plüschow escaped from the Donington Hall prisoner of war camp in 1915. Frederick Mors, an Austrian-born American serial killer, was declared insane and placed into the Matteawan Institution for the Insane in the United States in 1915. He escaped in 1916 and was never seen again but supposedly resurfaced in Connecticut in 1917. His body was possibly found in 1923 and identified as a suicide. In 1921, at age 22 Victor Folke Nelson made a sensational and highly publicized run and escape"Victor F. Nelson Eludes Pursuers." Boston Evening Globe. 12 May 1921. from a line of 13 prisoners after attending chapel at the Charlestown State Prison. Despite an attempted intervening tackle from a prisoner trusty and bullets from a guard's gun, Nelson ran some distance, leapt, caught the lower end of the window bars, and scaled the 40-foot high wall of the prison's Cherry Hill section.Merrill, Anthony. "The Man Who Broke Charlestown". Boston Sunday Advertiser Green Magazine. 17 December 1939. At the top of the wall, he performed "what was always believed an impossible stunt: throwing his body across a 10-foot space to the wall,""Back in Prison After Restful Sojourn Here". Daily Springfield Republican. 12 September 1921. where he managed to catch hold of the coping of a nearby structure and then to drop 30 feet down to the Boston and Maine railroad tracks."Victor F. Nelson, Notorious Ex-Convict, Believed Poisoned". The Boston Herald. 10 December 1939. He was convinced to return to prison by his respected mentor and progressive penologist Thomas Mott Osborne several months later."Movie Made Escaped Convict Go Back to Charleston Prison". The Boston Sunday Post. 17 December 1939. In 1922, an IRA bomb blew a hole in the wall of the Jail in Dundalk, County Louth, Ireland. 106 IRA prisoners escaped. A few weeks later, these same prisoners returned fully armed, and took over the whole prison, freeing remaining prisoners. Leonard T. Fristoe was born 15 January 1893 and was imprisoned for double murder in 1920 of two Sheriff's deputies in Nevada.ODMP memorial He escaped from Carson State Prison, Nevada, in 1923 after seizing an opportunity to escape after he and another inmate drove the police warden to a brothel. He lived for 46 years under the alias of Claude R. Willis, before being turned in by his son, Claude R. Willis Jr, after an argument. He stated that he only killed the deputies because they fired at him first, and also confessed to killing a man named Rowe in Curero, Texas, about two years after his escape. After serving 5 months in prison, the Nevada Pardon Board ordered he be released from Carson State Prison, despite the fact he had only served 2 1/2 years of the life sentence given to him in 1920. Whilst the chairman of the board, Gov. Paul Laxalt, disagreed with the killings of the two deputies, he saw no point in keeping a frail old man in jail, stating that 5 months behind bars is psychologically years for a 77-year-old man. He died of a respiratory infection on 13 March 1976 in Denver City, Texas. Theodorus van Berkel, a Dutch national who was charged with the rape of a young woman in Green Bay, Wisconsin, in 1930, escaped from prison after sawing off the bars of his cell and bending them with a smuggled metal pipe. He was captured, but escaped with another prisoner two weeks later using a similar method. Van Berkel and his accomplice were caught within hours of each other a day later. John Dillinger served time at the Indiana State Penitentiary at Michigan City, until 1933, when he was paroled. Within four months, he was back in jail in Lima, Ohio, but his gang sprang him, killing the jailer, Sheriff Jessie Sarber. Most of the gang was captured again by the end of the year in Tucson, Arizona, due to a fire at the Historic Hotel Congress. Dillinger alone was sent to the Lake County jail in Crown Point, Indiana. He was to face trial for the suspected killing of police officer William O'Malley during a bank shootout in East Chicago, Indiana, some time after his escape from jail. During this time on trial, a famous photograph was taken of Dillinger putting his arm on prosecutor Robert Estill's shoulder when suggested to him by reporters. On 3 March 1934, Dillinger escaped from the "escape-proof" (as it was dubbed by local authorities at the time) Crown Point, Indiana county jail, which was guarded by many police officers and national guardsmen. Newspapers reported that Dillinger had escaped using a fake gun made from wood, blackened and shined with shoe polish. French prisoner René Belbenoît escaped from the penal colony of French Guiana on 2 March 1935, when he and five others took to the sea with a boat they had bought. After a series of daring adventures, during which all of the other escapees were captured, he reached the United States in 1937. In 1938 his account, Dry Guillotine, was published. Belbenoît had written it in French and it was translated in English by Preston Rambo. It went through 14 printings in less than a year. Japanese prisoner Yoshie Shiratori broke out of prison four times, first from Aomori Prison (1936), Akita Prison (1942), Abashiri Prison (1944), and Sapporo Prison (1947). A novel and TV-drama Hagoku was based on his true story. Fort San Cristóbal is located on the top of the mountain San Cristóbal, which is very close (4 km) to Pamplona, Spain. Built inside the mountain, it served as a prison despite the fact that it had been obsolete since its opening in 1919, due to its weakness against aviation. On 22 May 1938, during the Spanish Civil War, around 30 prisoners organised a mutiny for a massive prison break. 792 prisoners fled but only three succeeded in getting to the French border; 585 were arrested, 211 died and 14 of the arrested who were considered the leaders were sentenced to death. Most fugitives were intercepted during the following days. In 1988, a sculpture was erected to honour the memory of the prisoners who died there. The fort ceased to be a prison in 1945. Colditz Castle was used as an "escape-proof" prisoner-of-war camp during World War II, but over the course of 300 escape attempts, 130 prisoners escaped. Thirty escapees eventually managed to reach friendly territory. The men had tunneled, disguised themselves as guards, workmen or women, sneaked away through sewer drains, and even built a glider in a plan to get over the wall. André Devigny, a French resistance fighter during World War II, escaped Montluc Military Prison in Lyon with his cellmate in April 1943. French author Henri Charrière tried to escape in vain several times, but eventually was successful in 1943. His story, Papillon, was published and filmed under the same name. Following his arrest in July 1943 and replacement by Marshal Pietro Badoglio as prime minister, Benito Mussolini was broken out of confinement by German forces in September 1943 overseen by SS-Hauptsturmführer Otto Skorzeny and Major Harald Mors in the Gran Sasso raid. In the Great Escape, 76 Allied POWs (primarily Commonwealth airmen) escaped from Stalag Luft III during World War II. 73 of the escapees were captured and fifty of them were executed by the Gestapo, while only three succeeded in reaching neutral territories. In the Cowra breakout, at least 545 out of 1,004 Japanese POWs escaped from Number 12 POW Compound at Cowra, Australia, on the night of 4 August 1944. Out of the roughly 500 escapees, 231 died and 108 were wounded. 31 killed themselves and 12 were burnt to death in huts set on fire by the Japanese. Sixteen of the wounded showed signs of attempted suicide. In the Latrun Prison break, 20 members of the Jewish terrorist group Lehi escaped from Latrun prison camp in Latrun, Mandatory Palestine (now Israel), through a 76 meter long tunnel on the night of 31 October 1943. 97 Italians escaped from Camp 14 at Doonfoot, Ayr, Scotland, on 15 December 1944. When the Italian fascist regime in Italy collapsed in July 1943 the new Italian Government signed an armistice with the Allies. Most Italian POWs held in the UK were released back into the command of Italy but a few were identified as committed fascists and were detained at Camp 14. After some unrest in the camp the large scale breakout occurred through a short tunnel. They were all recaptured within a week.