Guest Stars Gretchen Mol as Gillian Darmody Jack Huston as Richard Harrow Greg Antonacci as Johnny Torrio Max Casella as Leo D'Alessio Christopher McDonald as Harry Daugherty Edoardo Ballerini as Ignacious D'Alessio Danny Burstein as Lolly Steinman Geoff Pierson as Senator Walter Edge Co Starring Brady Noon as Tommy Darmody Connor Noon as Tommy Darmody Lucy Gallina as Emily Schroeder Josie Gallina as Emily Schroeder Rory McTigue as Teddy Schroeder Declan McTigue as Teddy Schroeder Victor Verhaeghe as Damien Fleming Robert Clohessy as Alderman Jim Neary Nisi Sturgis as June Thompson William Hill as Alderman George O'Neill Adam Mucci as Deputy Halloran Edward McGinty as Alderman Al Boyd 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 Jacqueline Knapp as Florence Harding
