James "Whitey" Bulger

Johnny Depp

John Connolly

Joel Edgerton

Bill Bulger

Benedict Cumberbatch

Marianne Connolly

Julianne Nicholson

Lindsey Cyr

Dakota Johnson

FBI Agent Charles McGuire

Kevin Bacon

Brian Halloran

Peter Sarsgaard

Kevin Weeks

Jesse Plemons

Stephen Flemmi

Rory Cochrane

John Morris

David Harbour

Deborah Hussey

Juno Temple

FBI Agent Robert Fitzpatrick

Adam Scott

Fred Wyshak

Corey Stoll

Johnny Martorano

W. Earl Brown

John Callahan

Bill Camp*

John Callahan

Bill Camp

Mickey Maloney

Mark Mahoney

John McIntyre

Brad Carter

Tommy King

Scott G. Anderson

DEA Agent Eric Olsen (Interrogator)

Lonnie Farmer

Mom Bulger

Mary Klug

Mary Bulger

Erica McDermott

Douglas Cyr

Luke Ryan

Buddy Leonard

Owen Burke

Jeremiah O'Sullivan

Lewis D. Wheeler

Joe Cahill

Billy Meleady

Mrs. Cody

Jamie Donnelly

Roger Wheeler

David De Beck

Roger Wheeler

David DeBeck

State Captain

Gary Galone

Officer Flynn

David Conley

Agent Scott Gariola

James Russo

Catherine Greig

Sienna Miller

Josh Bond

Jeremy Strong

McGuire's Secretary

Danae Nason

Young Boy

Bretton Manley

Anna Bjornsdottir

Berglind Jonsdottir

Irish Nationalist

Ciaran Crawford

FBI Wire Tech

Thomas Philip O'Neill

Joey

Joey Vacchio

Gennaro Angiulo

Bill Haims

Charlie McTiernan

Anthony Molinari

Charlie's Friend

Todd Ryan Jones

Charlie's Friend

Declan Mulvey

Agent James

Bates Wilder

Dick Lehr

Marc Carver

Gerard O'Neill

Richard Donelly

Prisoner

Brian A. White

FBI Agent

Peter Morse

Father Mackey

Tom Kemp

Michael Donahue

Patrick M. Walsh

DEA Agent

Naheem Garcia

Nurse

Kathryn A. Beauchamp

Drug Dealer

Stephen Curran

Sr. FBI Official

Robert Walsh

Drug Dealer

Darin X.L. MacEachern

Drug Dealer

Cary 'Big Shug' Guy

Crook

Sean Malone

Drug Dealer

Cary "Big Shug" Guy

Barman

Jack Neary

Boot Shop Owner

Jimmy Joe Maher

World Jai Alai Chairman

Forry Buckingham

Porthole Bartender

Danny DeMiller

Porthole Customer

Michael F. Murphy

DEA Agent Dan Doherty

Alexander Cook

Little Mary Bulger

Ava Cooper

Kathleen Bulger

Stella Cooper

Driver

Arthur Hiou

Floor Dancer (uncredited)

Julie Ann Dawson

The Mayor

Jim Powers

Walker

Jeff Kamps

Press Photographer

Susan Garibotto

Director

Scott Cooper