Guest Stars Connor Noon as Tommy Darmody 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 Brady Noon as Tommy Darmody Declan McTigue as Teddy Schroeder Josie Gallina as Emily Schroeder Eric LaRay Harvey as Dunn Purnsley Chris Caldovino as Tonino Sandrelli Julianne Nicholson as Esther Randolph Ivo Nandi as Joe Masseria Wrenn Schmidt as Julia Sagorsky Stephen Root as Gaston Means Mark Borkowski as Paul Sagorsky James Cromwell as Andrew William Mellon Anthony Gallo as Sam Moceri Jason Furlani as Caiozzo Rocco Parente as Falcone Anthony Engellis as Rossi Daniel Raymont as Daniel Marcus Ned Coulter as Dr. Hollis Nick Nappy as Sheriff Keck Co Starring Peter Claymore as Grey-Haired Man Steven L. Barron as Vocal Reporter Nicholas Julius as Gino Thomas Endres as Philadelphia Enquirer Reporter Ryan Redebaugh as Cop