Guest Stars Charlie Cox as Owen Slater Anatol Yusef as Meyer Lansky Victor Verhaeghe as Ward Boss Fleming Kevin O'Rourke as Mayor Edward Bader Ivo Nandi as Joe Masseria Christopher McDonald as Harry Daugherty Danny Burstein as Lolly Steinman Tom Aldredge as Ethan Thompson Wayne Duvall as Governor Edward I. Edwards Co Starring Connor Noon as Tommy Darmody Heather Lind as Katy Jacqueline Pennewill as Lillian Tracy Middendorf as Babette Peter Claymore as Grey-Haired Man Nisi Sturgis as June Thompson Stephen DeRosa as Eddie Cantor Pearce Bunting as Bill McCoy Amy Warren as Pauleen Tracy Sallows as Katheryn Bader Andrew Kober as Waiter Greg Harvey as Harrow's man Mike Lubik as Vitrola delivery man