 | James 'Whitey' Bulger |
 | John Connolly |
 | Billy Bulger |
 | Lindsey Cyr |
 | Charles McGuire |
 | Brian Halloran |
 | Kevin Weeks |
 | Steve Flemmi |
 | John Morris |
 | FBI Agent Robert Fitzpatrick |
 | Fred Wyshak |
 | Marianne Connolly |
 | John Martorano |
 | 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 |
 | Officer Flynn |
FBI Wire Tech | |
Joey, Big Italian | |
Jerry Angiulo | |
 | Charlie |
Charlie's Friend #1 | |
Charlie's Friend #2 | |
Agent James | |
Dick Lehr | |
Gerard O'Neill | |
 | State Captain |
 | Father Mackey |
Michael Donahue | |
 | DEA Agent |
Drug Dealer #3 | |
DEA Agent Dan Doherty | |
Little Mary Bulger | |
Kathleen Bulger | |
Parade Spectator | |
Parade spectator | |
TV News Reporter | |
 | Photographer |
Miami Pedestrian | |
Bar Patron | |
 | Orange Cart Vendor |
FBI Special Agent | |
Protestor | |
Breakfast Guest | |
Task Force Agent | |
Port Hole Bar Patron,Funeral Attendee | |
FBI Dir Wm Sessions | |
 | Young Boy |
Italian Mobster | |
 | The Mayor |
 | Agent Scott Gariola |
 | Josh Bond |
Police Officer | |
School Teacher | |
FBI Agent | |
FBI Agent | |
Parade Spectator | |
Mary Bulger | |
FBI task force agent |