16. The famous John Dillinger
John Dillinger is one of the most famous criminals of all time. His name is extremely well known worldwide for bank robbery and kidnapping. He is the kind of mastermind that will use every possibility to learn and become an expert at what he does. Even when put into a harsh situation, he will continue learning from it and use it to his advantage at the perfect time. On his first imprisonment, he was heard saying that he will be even more vicious a criminal than ever after he gets out. John Dillinger was paroled in 1933, after a nine and a half year stint.
Needless to say, he kept his word and continued with his craft. Using everything he learned from his time in jail, he started to rob banks. In June of 1933, he robbed a bank for the first time, making off with $10,000. Later in the same year, he was arrested. After searching him, the police discovered a paper that to be a prison escape plan, but he wouldn’t give away any details. Apparently, he knew what he was doing. Dillinger and his gang members tried to act like police officers but it didn’t go over so well, so they had to shoot the guards. Being out of prison again, he robbed more banks. Caught up and sent back to prison, this time he made a fake gun out of wood to frighten the security officers. In 1934, Dillinger was shot and killed in a setup by the FBI outside of a movie theater in Chicago.
17. Billy Hayes
Billy Hayes is an American writer, actor and film director. However, his early life was far from good. On October 7, 1970, Hayes was arrested for drug abuse in Turkey and was sentenced to life where he spent the hardest of his days. Although his time in prison was a misery, it seemed that suffering helped him put his life into perspective, making it clear what he was born to do. Eventually, his conviction was decreased to 30 years due to multiple prison transfers. He came to a point that couldn’t spend any more days in jail. Hayes used everything he learned about the prison’s security flaws and escaped. Shortly after, he shared his experiences in Turkey in the book “Midnight Express” that led him to a successful career.
18. Alfie “Houdini” Hinds
Alfie Hinds was an orphan who became a criminal at an early age. In 1953, he got arrested for a jewelry robbery. However, Hinds later escaped from the prison after sneaking through the locked doors and over a 20-foot prison wall for which he became known as “Houdini” Hinds. Breaking out was the kind of challenge that Hinds would easily deal with. He had a highly-functional mind that made it possible to see the legal system’s flaws and use them whenever was needed to avoid prosecution. It is not a surprise that Hinds could also see every small gap in the prisons’ security system, which got him out every time.
19. 2015 Clinton Correctional Facility Escape
In June 6, 2015, Richard Matt and David Sweat, two inmates at the Clinton Correctional Facility, а maximum security state prison for men located in the Village of Dannemora, New York, were found missing from their prison cells. Both prisoners were serving life for murder. Matt and Sweat had worked in the prison’s tailor shop from which they took their materials and tools for the escape. They cut neat rectangular holes in the steel at the backs of their cells. They made dummies from sweatshirts and put them into their beds to prevent discovery during regular cell checks by guards. With the help from a staff member, they crawled through a pipe when they made their escape in early June. Sweat was caught about 15 miles north. Matt was killed 30 miles away from the prison.
20. Sarah Jo Pender
Sarah Jo Pender is an American woman who was convicted of murder and imprisoned in the Rockville Correctional Facility. Rockville is a medium-security prison located about 50 miles from of Indianapolis. On the 4th of August, 2008, with the help of a guard from the facility, Scott Spitler Sr., and Jamie Long, her former cellmate Pender broke out. The escape was planned shortly before it happened with a cell-phone given to her by the prison guard. He also gave Pender clothing to change into and got her out with his personal vehicle – assistance that cost Spitler 8 years in jail. In September 2008, Pender lived in a North Side Chicago neighborhood using the name Ashley Thompson and was turned in to the police after a neighbor saw an America’s Most Wanted rerun with Sarah Jo Pender in their list.