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as FBI Agent Robert Fitzpatrick
as DEA Agent Dan Doherty
as Charlie McTiernan
as Driver
as Little Mary Bulger
as Agent James
as Billy Bulger
as Anna Bjornsdottir
as John Callahan
as Gennaro Angiulo
as Joe Cahill
as John McIntyre
as Young Boy
as Prisoner
as Drug Dealer
as Irish Nationalist
as Fred Wyshak
as Lindsey Cyr
as McGuire's Secretary
as Porthole Bartender
as Officer Flynn
as Roger Wheeler
as John Morris
as Charlie's Friend
as Mary Bulger
as World Jai Alai Chairman
as State Captain
as Barman
as Agent Scott Gariola
as Mrs. Cody
as Walker
as Kevin Weeks
as The Mayor
as Boot Shop Owner
as John Connolly
as Joey, Big Italian
as James 'Whitey' Bulger
as Marianne Connolly
as Deborah Hussey
as Nurse
as FBI Agent Charles McGuire
as Jeremiah O'Sullivan
as DEA Agent Eric Olsen (Interrogator)
as Douglas Cyr
as Dick Lehr
as Mickey Maloney
as Mom Bulger
as Porthole Customer
as DEA Agent
as Buddy Leonard
as Michael Donahue
as FBI Agent
as Brian Halloran
as Gerard O'Neill
as Sr. FBI Official (voice)
as Stephen Flemmi
as Tommy King
as Crook
as Kathleen Bulger
as Press Photographer
as FBI Wire Tech
as Father Mackey
as John Martorano