Guest Stars Charlie Cox as Owen Slater Anatol Yusef as Meyer Lansky Rory McTigue as Teddy Schroeder Lucy Gallina as Emily Schroeder Dominic Chianese as Leander Cephas Whitlock Glenn Fleshler as George Remus Peter McRobbie as Supervisor Elliot Christopher McDonald as Harry Daugherty William Forsythe as Manny Horvitz Enid Graham as Rose Van Alden Michael Cumpsty as Father Brennan Geoff Pierson as Senator Walter Edge Nick Sandow as Waxey Gordon Co Starring Connor Noon as Tommy Darmody Heather Lind as Katy Jacqueline Pennewill as Lillian Joseph Aniska as Agent Stan Sawicki Rony Clanton as Langston Pearce Bunting as Bill McCoy Peter Van Wagner as Isaac Ginsburg Ed Jewett as Jess Smith Bill Sage as Solomon Bishop Julian Rozzell Jr. as Harlan Joel Brady as Agent Clarkson T.J. Kenneally as Charles Kenneth Thorogood AKA "Chip" Solomon Shiv as Herman "Chayem" Kaufman John Mainieri as Hotel Manager Edward James Hyland as Judge Ketchum Brad Aldous as Photographer Katy Boyer as Chip's Girl Angelo Berkowitz as Driver McKenna Kerrigan as Nurse