Winter Hill Gang

- Started: 1955
- Current alleged leader: George Hogan
- Previous leaders: Kevin Weeks, James "Whitey" Bulger, Howard Winter, James McLean

Named after their original home neighborhood in Somerville, Massachusetts, the Winter Hill Gang is an Irish organized crime syndicate formerly led by FBI most wanted list member James "Whitey" Bulger. The gang is reputed to be the basis for the organized crime group in Martin Scorsese's The Departed.
December 4, 2008: Former FBI agent John J. Connolly could face 30-years to life in prison for the gangland-style killing of businessman John Callahan. Connolly, who was fictionally portrayed by Matt Damon in The Departed, worked for the FBI for two decades in Boston.CNN.com: Rogue FBI agent breaks silence at sentencing (December 4, 2004)
Winter Hill Facts
1. Neighborhood in Somerville, MA
2. Bordered by I-93 on the northeast, Central and Ash on the northwest, Medford Street on the southwest, and McGrath Highway (Route 28) on the southeast
3. Currently heavily Brazilian
James "Whitey" Bulger Facts
1. Born: September 3, 1979
2. Birthplace: Dorchester, Massachusetts
3. Brother: William Bulger, former president of the Massachusetts State Senate
4. 1952: Honorably discharged from U.S. Air Force
5. 1975-1995: FBI informant
6. 1979-1995: Ran the Winter Hill Gang
7. FBI: Ten Most Wanted Fugitives list
8. Wanted for 19 murders, money laundering, extortion, drug dealing
Winter Hill Gang and The Departed

Martin Scorsese has said that the character of Frank Costello (played by Jack Nicholson) in The Departed is extremely loosely based on Whitey Bulger. The DVD contains a documentary titled Stranger Than Fiction: The True Story of Whitey Bulger, Southie and 'The Departed,' which explicitly details the parallels between the real-life Winter Hill Gang and the events in the film.