James 'Whitey' Bulger

John Connolly

Marianne Connolly

Lindsey Cyr

FBI Agent Charles McGuire

Billy Bulger

Brian Halloran

Deborah Hussey

Kevin Weeks

John Morris

FBI Agent Robert Fitzpatrick

Fred Wyshak

John Callahan

Mickey Maloney

John McIntyre

Tommy King

DEA Agent Eric Olsen (Interrogator)

Mom Bulger

Mary Bulger

Douglas Cyr

Buddy Leonard

Jeremiah O'Sullivan

Joe Cahill

Mrs. Cody

Roger Wheeler

State Captain

Stephen Flemmi

Agent Scott Gariola

Josh Bond

McGuire's Secretary

Young Boy

Anna Bjornsdottir

Officer Flynn

Irish Nationalist

FBI Wire Tech

Joey, Big Italian

Gennaro Angiulo

Charlie McTiernan

Charlie's Friend

Agent James

Dick Lehr

Gerard O'Neill

Prisoner

FBI Agent

Father Mackey

Michael Donahue

DEA Agent

Nurse

Drug Dealer

Drug Dealer

Drug Dealer

Crook

Barman

Boot Shop Owner

World Jai Alai Chairman

Porthole Bartender

Porthole Customer

DEA Agent Dan Doherty

Little Mary Bulger

Kathleen Bulger

Driver

Charlie's Friend

Floor Dancer (uncredited)

Trevor Williams (uncredited)

Sr. FBI Official (voice)

John Martorano

The Mayor

Walker

Press Photographer

Marion Hussey (uncredited)

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