The Kennedys of Massachusetts: Cast Rate: –☹️ Very Bad🙁 Bad😐 Average🙂 Good😃 Excellent🤩 Super! ★ Save Rating✔ Rating Saved! Notify me: –about new episodeabout new seasonabout end of season Subscribe✔ Subscription Saved! The Kennedys of Massachusetts Drama, History, Family United States GeneralEpisodesCastCharactersGallery Cast See full cast → William Petersen as Joseph P. "Joe" Kennedy, Sr. Annette O'Toole as Rose Kennedy Steven Weber as John F. "Jack" Kennedy Casey Affleck as Robert Kennedy - Ages 12-15 Cindy Baer as Rose's Friend - 1906 Deborah Bancroft as Sissy Thomas Paul Bronk as Bartender Sullivan Brown as King George Allyn Burrows as G.I. Karen Chaffee as Patricia Kennedy - Ages 13-14 Ken Cheeseman as Ormsby-Gore Mara Clark as Maid Ruth Jordan Clarke as James Reedy Richard Clarke as Neville Chamberlain Father Coppenrath as Priest Joe Costa as David Sarnoff Dawn Couch as Cora Michael Cumpsty as Billy Hartington