Guest Stars Anatol Yusef as Meyer Lansky Kevin O'Rourke as Mayor Edward Bader Charlie Cox as Owen Sleater Victor Verhaeghe as Damien Fleming Robert Clohessy as Alderman Jim Neary Eric LaRay Harvey as Dunn Purnsley Adam Mucci as Deputy Halloran Dominic Chianese as Leander Cephas Whitlock Julianne Nicholson as Esther Randolph William Forsythe as Manny Horvitz Michael Cumpsty as Father Ed Brennan Co Starring Brady Noon as Tommy Darmody Josie Gallina as Emily Schroeder Lucy Gallina as Emily Schroeder Connor Noon as Tommy Darmody Rory McTigue as Teddy Schroeder Declan McTigue as Teddy Schroeder Christiane Seidel as Sigrid Mueller Heather Lind as Katy Edward McGinty as Alderman Al Boyd Jacqueline Pennewill as Lillian Brandon Zumsteg as Brian Thompson Rony Clanton as Langston Peter Claymore as Grey-Haired Man Curt Bouril as Clifford Lathrop David Aaron Baker as Bill Fallon Thomas Philip O'Neill as Dick Halsey Samuel Taylor as Paddy Ryan John Keating as Ernie Moran Trisha McCormick as Eunice Randall Newsome as Douglas Wallbridge 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