James 'Whitey' Bulger
John Connolly
Billy Bulger
Lindsey Cyr
FBI Agent Charles McGuire
Brian Halloran
Kevin Weeks
Stephen Flemmi
John Morris
FBI Agent Robert Fitzpatrick
Fred Wyshak
Marianne Connolly
John Martorano (as W Earl Brown)
John Callahan
Deborah Hussey
Mickey Maloney
John McIntyre
Tommy King
DEA Agent Eric Olsen (Interrogator)
Mom Bulger
Mary Bulger
Douglas Cyr
Buddy Leonard
Jeremiah O'Sullivan
Sr. FBI Official (voice)
Joe Cahill
Mrs. Cody
Roger Wheeler (as David DeBeck)
Officer Flynn
Irish Nationalist
FBI Wire Tech
Joey, Big Italian
Gennaro Angiulo
Charlie McTiernan
Charlie's Friend
Agent James
Dick Lehr
Gerard O'Neill
State Captain
Prisoner
FBI Agent (as Peter J. Morse)
Father Mackey
Michael Donahue (as Patrick M. Walsh Jr.)
DEA Agent
Nurse
Drug Dealer
Drug Dealer (as Darin XL MacEachern)
Drug Dealer (as Cary Big Shug Guy)
Crook
Barman
Boot Shop Owner
World Jai Alai Chairman
Porthole Bartender
Porthole Customer
DEA Agent Dan Doherty
Little Mary Bulger
Kathleen Bulger
Pancake Breakfast Attendee (uncredited)
FBI Agent (uncredited)
Federal Agent (uncredited)
Bar Patron (uncredited)
Teddy (uncredited)
TV News Reporter (uncredited)
Photographer (uncredited)
FBI Agent's Wife (uncredited)
Motorist (uncredited)
Funeral Mourner (uncredited)
Guard (uncredited)
Politician (uncredited)
Vintage Car Driver (uncredited)
Press Cameraman / Southie Spectator (uncredited)
Cameraman (uncredited)
Dead Italian Mobster #1 (uncredited)
Pedestrian (uncredited)
Protestor (uncredited)
Self (archive footage) (uncredited)
Alice Sessions (uncredited)
Restaurant Bar Patron (uncredited)
Mobster (uncredited)
Protester (uncredited)
Miami Pedestrian (uncredited)
LA FBI Task Agent 1 (uncredited)
Child at Beach (uncredited)
Bulger Cousin (uncredited)
Irish Mobster (uncredited)
Floor Dancer (uncredited)
Angiulo's Soldier (uncredited)
Background (uncredited)
Rocco (uncredited)
Gangster (uncredited)
Reporter (uncredited)
Parishioner / Pancake Breakfast Attendee (uncredited)
Street Protester (uncredited)
Orange Cart Vendor (uncredited)
FBI Special Agent (uncredited)
Breakfast Guest (uncredited)
Parade spectator (uncredited)
Press Photographer (uncredited)
Core FBI Agent (uncredited)
Cafeteria Patron (uncredited)
Mourner (uncredited)
Irish American Woman (uncredited)
Mafia Guy and 1972 Cadillac (uncredited)
Italian Woman (uncredited)
FBI Secretary (uncredited)
Bartender (uncredited)
Disco Dancer (uncredited)
Port Hole Bar Patron / Funeral Attendee (uncredited)
Republican Against Busing (uncredited)
Politicians Wife (uncredited)
Anna Bjornsdottir (uncredited)
Flemmi's Girlfriend (uncredited)
Walker (uncredited)
Marion Hussey (uncredited)
FBI Dir Wm Sessions (uncredited)
Lowlife #2 (uncredited)
Havana Bar Patron (uncredited)
Commisioner DiGrazia (uncredited)
Protesting Mom (uncredited)
Spectator (uncredited)
Port Hole Bar Patron (uncredited)
Wire Tech (uncredited)
Boston PD Tactical Patrol Force (uncredited)
Young Boy (uncredited)
Teen Boy on Banana Bike (uncredited)
Italian Mobster (uncredited)
Mr. Saint Paddy (uncredited)
Restaurant Patron (uncredited)
Little Billy Bulger (uncredited)
McGuire's Secretary (uncredited)
Dock Worker (uncredited)
Girl at Parade (uncredited)
Parade Spectator (uncredited)
Extra (uncredited)
Club Goer (uncredited)
Bar Patron / Protester (uncredited)
Eddie Phillips (uncredited)
Mary Bulger (uncredited)
The Mayor (uncredited)
Lowlife #1 (Halloran's Drug Dealer) (uncredited)
School Teacher (uncredited)
Driver in Black Datsun (uncredited)
Funeral Attendee (uncredited)
Arresting FBI Agent (uncredited)
Waiter (uncredited)
Latin Dancer (uncredited)
Agent Scott Gariola (uncredited)
Chris Bulger (uncredited)
Boston Firefighter (uncredited)
Irish Girl (uncredited)
Parade Kid (uncredited)
Parade attendant (uncredited)
Josh Bond (uncredited)
Police Officer (uncredited)
LA FBI Agent (uncredited)
Waitress (uncredited)
Winter Hill Gangster (uncredited)
FBI Task Force Agent (uncredited)
Beachgoer / Restaurant Patron / Nightclub Partier (uncredited)
St. Paddy's Day Patron (uncredited)
Angiulo Mobster (uncredited)
Drunk Walker (uncredited)