Guest Stars Gretchen Mol as Gillian Darmody Jack Huston as Richard Harrow Rory McTigue as Teddy Schroeder Lucy Gallina as Emily Schroeder Victor Verhaeghe as Ward Boss Fleming Robert Clohessy as Jim Neary Greg Antonacci as Johnny Torrio Declan McTigue as Teddy Schroeder Josie Gallina as Emily Schroeder Christopher McDonald as Harry Daugherty Max Casella as Leo D'Alessio Edoardo Ballerini as Ignacious D'Alessio Danny Burstein as Lolly Steinman Geoff Pierson as Senator Walter Edge Co Starring Connor Noon as Tommy Darmody Brady Noon as Tommy Darmody William Hill as Ward Boss O'Neill Adam Mucci as Deputy Halloran Edward McGinty as Alderman Al Boyd Nisi Sturgis as June Thompson Kevin Henderson as Dr. Carl Surran Enid Graham as Rose Van Alden David Aaron Baker as Bill Fallon Anna Katarina as Isabelle Jeunet Nicholas Martino as Pius D'Alessio Al Linea as Matteo D'Allessio Megan Reinking as Anabelle Virginia Kull as Nan Britton Susan Varon as Madam Regina Nicholas Julius as Gino Kenn Mann as Postal Worker Benjamin Livingston as Hotel Manager Frank Ridley as Conductor Malachy Cleary as Warren G. Harding Anthony Cerbone as Antonio Christian Kauffmann as Judge Graves Carmine Raspaolo as Angelo Daniel Cox as Jess Smith
