Guest Stars Charlie Cox as Owen Slater Anatol Yusef as Meyer Lansky Victor Verhaeghe as Ward Boss Fleming Robert Clohessy as Jim Neary Kevin O'Rourke as Mayor Edward Bader Declan McTigue as Teddy Schroeder Josie Gallina as Emily Schroeder Eric LaRay Harvey as Dunn Purnsley Dominic Chianese as Leander Cephas Whitlock Ted Rooney as John McGarrigle Co Starring Heather Lind as Katy William Hill as Ward Boss O'Neill Edward McGinty as Alderman Al Boyd Jacqueline Pennewill as Lillian Rony Clanton as Langston Peter Van Wagner as Isaac Ginsburg Michael Zegen as Benjamin Siegel Samuel Taylor as Paddy Ryan Bill Sage as Solomon Bishop John Keating as Ernie Moran Amy Warren as Pauleen Natalie Wachen as Lenore White Steven L. Barron as Vocal Reporter Thomas Endres as Philadelphia Enquirer Reporter Trisha McCormick as Eunice John Cenatiempo as Scarpelli Truck Hudson as Timothy Don Puglisi as Len Rob Kramer as Poker Player #1 Michael McEachran as Harold Mario Macaluso as Incrocci Joseph Tudisco as Poker Player #2 Jonathan Baston as Cornelius Jeff Norris as Sheriff's Deputy #2 Jack E. Moran as Sheriff's Deputy #1 Alex Cranmer as Talmer Omar Sharif Scroggins as Harold C. Madison Barthelemy Atsin as Noah Hookway