James 'Whitey' Bulger
In 1975 as a member of the Winter Hill Gang, Bulger became an FBI informant. Bulger and Stephen Flemmi helped the FBI build a case against the Italian Mafia. Bulger and Flemmi built a drug-trafficking and racketeering empire in Southie. In the early '90s, the FBI dropped them as informants. In 1995, federal charges were handed down against Bulger and friends. Bulger was on the run for more than 16 years until his capture on June 22, 2011.