Initially a hero of the Revolutionary War, Benedict Arnold later switched sides and fought for the British, making him one of the biggest traitors in American History. He was in the process of handing over West Point to the British when the U.S. uncovered the conspiracy and sought to capture and kill Arnold. The commander fled to London, where he died in obscurity in 1801.

Tekashi was a celebrated rapper with viral hits before his criminal undertakings were revealed. While he's far from the first rapper to be arrested for his active gang ties, he's one of few to face over 30 years in jail for attempted murder.