Les Kennedy

Greg Kinnear

Jack Kennedy

Barry Pepper

Robert F. Kennedy

Katie Holmes

Jackie Kennedy

Tom Wilkinson

Joe Kennedy Sr.

Diana Hardcastle

Rose Kennedy

Kristin Booth

Ethel Kennedy

Janelle Hutchison

Evelyn Lincoln

Rothaford Gray

Agent Abraham Bolden

Rachel Wilson

Michelle

Serge Houde

Sam Giancana

Barry Flatman

General Thomas Bennett

Dan Lett

McGeorge Bundy

Enrico Colantoni

J. Edgar Hoover

Don Allison

Lyndon B. Johnson

Megan Vincent

Judy Campbell

John White

Young Jack Kennedy

Gabriel Hogan

Joe Kennedy Jr.

Alex Poch-Goldin

Jimmy Ryan

Jonathan Whittaker

Robert McNamara

Chris Diamantopoulos

Frank Sinatra

Peter MacNeill

Governor Ross Barnett

Charlotte Sullivan

Marilyn Monroe

Allan Royal

Allen Dulles

Jack Ruby

Self (archive footage)

Shauna MacDonald

Janet Auchincloss

Lex Cassar

Mike

Henry Cabot Lodge

Self (archive footage) (uncredited)

Pat Nixon

Self (archive footage) (uncredited)

Richard Nixon

Self (archive footage) (uncredited)