Guest Stars Charlie Cox as Owen Slater Anatol Yusef as Meyer Lansky Rory McTigue as Teddy Schroeder Lucy Gallina as Emily Schroeder Victor Verhaeghe as Ward Boss Fleming Robert Clohessy as Jim Neary Kevin O'Rourke as Mayor Edward Bader Eric LaRay Harvey as Dunn Purnsley Julianne Nicholson as Esther Randolph Dominic Chianese as Leander Cephas Whitlock William Forsythe as Manny Horvitz Michael Cumpsty as Father Brennan Co Starring Connor Noon as Tommy Darmody Heather Lind as Katy Adam Mucci as Deputy Halloran Edward McGinty as Alderman Al Boyd Jacqueline Pennewill as Lillian Rony Clanton as Langston Christiane Seidel as Sigrid Peter Claymore as Grey-Haired Man Curt Bouril as Clifford Lathrop Brandon Zumsteg as Brian Thompson David Aaron Baker as Bill Fallon Samuel Taylor as Paddy Ryan Thomas Philip O'Neill as Dick Halsey John Keating as Ernie Moran Randall Newsome as Douglas Wallbridge Trisha McCormick as Eunice Charlotte Booker as Cicero Landlady Christian Davidock as Dick Heatherton Dan Sharkey as Herb Crocker Denny Dale Bess as Klansman Informant Donte Bonner as Chalky's Man #1 Ian Scott McGregor as Halloran's attorney Naomi McDougall Jones as Screaming Secretary Roy Milton Davis as Pony Wrangler Tim House as Klansman Raider #3 Ian Stuart as Judge