The most infamous gangster in American history, Capone ruled Chicago with an iron fist during Prohibition until a tax accountant took him down.
The Violence: He was the suspect behind the St. Valentine’s Day Massacre, where seven rival gang members were lined up and executed, though he was never charged for it.
The Untouchable Charge: Despite his long list of violent crimes, the FBI and Treasury agents finally caught him on tax evasion. In 1931, he was sentenced to 11 years in federal prison.
Alcatraz: He was one of the first inmates at the new Alcatraz prison. While there, his health deteriorated rapidly due to untreated syphilis, leaving him mentally incapacitated upon release.