Aliança do Crime
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Johnny DeppJames 'Whitey' Bulger
Joel EdgertonJohn Connolly
Julianne NicholsonMarianne Connolly
Dakota JohnsonLindsey Cyr
Kevin BaconFBI Agent Charles McGuire
Benedict CumberbatchBilly Bulger
Peter SarsgaardBrian Halloran
Juno TempleDeborah Hussey
Jesse PlemonsKevin Weeks
David HarbourJohn Morris
Adam ScottFBI Agent Robert Fitzpatrick
Corey StollFred Wyshak
Bill CampJohn Callahan- Mark MahoneyMickey Maloney
Brad CarterJohn McIntyre
Scott G. AndersonTommy King
Lonnie FarmerDEA Agent Eric Olsen (Interrogator)- Mary KlugMom Bulger
Erica McDermottMary Bulger- Luke RyanDouglas Cyr
Owen BurkeBuddy Leonard
Lewis D. WheelerJeremiah O'Sullivan- Billy MeleadyJoe Cahill
Jamie DonnellyMrs. Cody
David De BeckRoger Wheeler
Gary GaloneState Captain
Rory CochraneStephen Flemmi
James RussoAgent Scott Gariola
Danae NasonMcGuire's Secretary- Bretton ManleyYoung Boy
- Berglind JonsdottirAnna Bjornsdottir
- David ConleyOfficer Flynn
- Ciaran CrawfordIrish Nationalist
Thomas Philip O'NeillFBI Wire Tech- Joey VacchioJoey, Big Italian
- Bill HaimsGennaro Angiulo
Anthony MolinariCharlie McTiernan
Declan MulveyCharlie's Friend
Bates WilderAgent James- Marc CarverDick Lehr
- Richard DonellyGerard O'Neill
Brian A. WhitePrisoner- Peter MorseFBI Agent
Tom KempFather Mackey
Patrick M. WalshMichael Donahue
Naheem GarciaDEA Agent- Kathryn A. BeauchampNurse
- Stephen CurranDrug Dealer
- Darin X.L. MacEachernDrug Dealer
Cary 'Big Shug' GuyDrug Dealer- Sean MaloneCrook
Jack NearyBarman- Jimmy Joe MaherBoot Shop Owner
- Forry BuckinghamWorld Jai Alai Chairman
- Danny DeMillerPorthole Bartender
- Michael F. MurphyPorthole Customer
- Alexander CookDEA Agent Dan Doherty
- Ava CooperLittle Mary Bulger
- Stella CooperKathleen Bulger
Arthur HiouDriver- Todd Ryan JonesCharlie's Friend
- Julie Ann DawsonFloor Dancer (sem créditos)
- FergaledgarTrevor Williams (sem créditos)
Robert E. WalshSr. FBI Official (voz)
W. Earl BrownJohn Martorano
Jim PowersThe Mayor
Jeff KampsWalker
Susan GarfieldPress Photographer
Colleen KellyMarion Hussey (sem créditos)