Guest Stars Anatol Yusef as Meyer Lansky Rory McTigue as Teddy Schroeder Lucy Gallina as Emily Schroeder Victor Verhaeghe as Ward Boss Fleming Kevin O'Rourke as Mayor Edward Bader Declan McTigue as Teddy Schroeder Josie Gallina as Emily Schroeder Chris Caldovino as Tonino Sandrelli Julianne Nicholson as Esther Randolph Ivo Nandi as Joe Masseria Glenn Fleshler as George Remus Meg Steedle as Billie Kent Nick Sandow as Waxey Gordon KC Wright as Josephine Co Starring Connor Noon as Tommy Darmody Brady Noon as Tommy Darmody Wrenn Schmidt as Julia Sagorsky Nisi Sturgis as June Thompson Kevin Henderson as Dr. Carl Surran Curt Bouril as Clifford Lathrop Brandon Zumsteg as Brian Thompson Marc D. Donovan as Sheriff Ramsey Joseph Riccobene as Frankie Yale Kate Loprest as Corrine Jenna Gavigan as Evelyn Jack Ferry as Gareth Murray Jim Schubin as Phil Gardner Kate Harpootlian as Dancer Bryant Carroll as "Wild Bill" Lovett Stephanie Mas as Dancer Tommaso Antico as Dancer Susan Barnes Walker as Tabor Heights Librarian Rhett Henckel as Treasury Agent Morgan S. Smith as Wellman's date Michaela Sprague as Dancer Lindsay Roebuck as Dancer John Alix as Dancer Danielle Froelich as Dancer Colby Lindeman as Dancer Clifton Samuels as Dancer Clem McIntosh as Wellman Christopher Cangero as Dancer Patrick Carroll as Peg Leg Lonergan