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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.

Current Status:
Boss: George "Georgie Boy" Hogan
Membership: 40-50
Areas of Interest: Boston

Years
Boss
Outcome
1952-1965

James "Buddy" McLean
Murdered
1965-1978

Howie Winter
Imprisoned, Released
1978-1995

Jimmy "Whitey" Bulger
Indicted, Fled
1995-2000

Kevin "Two" Weeks
Imprisoned, Defected
2000-Present
George "Georgie Boy" Hogan

Years
Lieutenant
Outcome
1980s-1993

John "Red" Shea
Imprisoned, Released
1980s-1995

Kevin "Two" Weeks
Promoted
1978-1995

Stevie "the Rifleman" Flemmi
Defected
1993-2000
George "Georgie Boy" Hogan
Promoted
2000-Present
William "Billy" Hogan

Years
Soldier
Outcome
1980s-1993

Eddie "Mac" MacKenzie
Imprisoned, Released
1970s-1979

Vincent "Jimmy the Bear" Flemmi
Imprisoned, Drug Overdose
1978-2000

Patrick "the Irishman" Nee
Imprisoned, Released, Retired