The Winter Hill Gang was founded in the early 1950s by James "Buddy" McLean. The Boston Irish Mob scene was a bloodbath through much of the 50s and 60s with two separate Irish Mob wars waging out, with The Winter Hill Gang being involved in either war. Buddy McLean was killed during the first war, however Howie Winter would lead to gang to victory in the second war absorbing the losing Charlestown Mob in to the Winter Hill Gang. Winter would be sent to prison leading to the reign of terror brought about by Whitey Bulger and Stevie Flemmi with the help from the FBI in John Connolly. Kevin Weeks, Whitey's protege, took the organization over from Whitey, but after being indicted Weeks agreed to show prosecutors some of the dead bodies from the Flemmi-Bulger reign of terror, and cooperate against Whitey if/when he is apprehended, although Weeks says it was all on Whitey's orders. George "Georgie Boy" Hogan is believed to be the leader of the Winter Hill Gang.
Boss: George "Georgie Boy" Hogan
Areas of Interest: Boston