Guest Stars Gretchen Mol as Gillian Darmody Greg Antonacci as Johnny Torrio Peter McRobbie as Supervisor Frederick Elliot Erik Weiner as Agent Eric Sebso Edoardo Ballerini as Ignacious D'Alessio Chris Mulkey as Boss Frank Hague Dana Ivey as Mrs. McGarry Co Starring Lucy Gallina as Emily Schroeder Josie Gallina as Emily Schroeder Declan McTigue as Teddy Schroeder Rory McTigue as Teddy Schroeder William Hill as Alderman George O'Neill Peter Claymore as Grey-Haired Man Enid Graham as Rose Van Alden Alex Eckstein as Sonny Capone Caleb Eckstein as Sonny Capone Ben Eckstein as Sonny Capone Anna Katarina as Isabelle Jeunet Nicholas Martino as Pius D'Alessio Megan Reinking as Anabelle Marcella Lentz-Pope as Mae Capone Jodie Sanders as Ruby Kylie Sanders as Ruby Barbara Tirrell as Edith Mat Hostetler as Agent Keener Johann Carlo as Teresina Capone Chris Cenatiempo as Bouncer Frank Shattuck as Charlie Sheridan Faith Sandberg as Kitty Whitney Bashor as Coat Check Girl Lauren Sharpe as Singer Maranda Barskey as Singing Whore