- 04:13 PM, Sep 21
Bulger was the head of South Boston's Winter Hill Gang, and fled before his indictment for federal racketeering in January 1995. It turns out he was a longtime FBI informant (an inspiration for Jack Nicholson's character in The Departed) who had been warned by his corrupt handler, former FBI agent John J. Connolly Jr. (the basis for Damon's Departed character). Connolly Jr. tipped off Bulger about his pending arrest, and Bulger stayed on the lam for sixteen years before he was caught living by the beach with his girlfriend. He was 81 at the time of his arrest.