Guest Stars Jack Huston as Richard Harrow Anatol Yusef as Meyer Lansky Lucy Gallina as Emily Schroeder Rory McTigue as Teddy Schroeder Robert Clohessy as Jim Neary Kevin O'Rourke as Mayor Edward Bader Greg Antonacci as Johnny Torrio Declan McTigue as Teddy Schroeder Josie Gallina as Emily Schroeder Erik Weiner as Agent Sebso Peter McRobbie as Supervisor Elliot Max Casella as Leo D'Alessio Lisa Joyce as Mary Dittrich Josiah Early as Robert Dittrich Dana Ivey as Mrs. McGarry Co Starring Connor Noon as Tommy Darmody Brady Noon as Tommy Darmody William Hill as Ward Boss O'Neill Adam Mucci as Deputy Halloran Peter Claymore as Grey-Haired Man Al Linea as Matteo D'Allessio John Rue as Mayor Harry Bacharach Virginia Kull as Nan Britton Joseph Caniano as Jake Guzik Tracy Sallows as Katheryn Bader Nicholas Julius as Gino Louis Vanaria as Lucien D'Alessio Eric Lenox Abrams as Jerome Susan Wands as Mrs. O'Neil Fiana Toibin as Mrs. Neary Chris Cenatiempo as Bouncer Maggie Steele as Odette Dan Sklar as Rabbi David Schallip as Wendell Eliezer Meyer as Rabbi Elli Matthew Schallip as Wendell