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 Kevin O'Rourke as Mayor Edward Bader William Forsythe as Manny Horvitz Enid Graham as Rose Van Alden Chris Mulkey as Boss Frank Hague Jennifer Ferrin as Carolyn Rothstein Co Starring Connor Noon as Tommy Darmody Heather Lind as Katy Jacqueline Pennewill as Lillian Joseph Aniska as Agent Stan Sawicki Kevin Henderson as Dr. Carl Surran Pearce Bunting as Bill McCoy Peter Van Wagner as Isaac Ginsburg Michael Zegen as Benjamin Siegel John Keating as Ernie Moran Bill Sage as Solomon Bishop Franklin Ojeda Smith as Deacon Lemuel Cuffy Amy Warren as Pauleen Justiin A. Davis as Lester White Joel Brady as Agent Clarkson Natalie Wachen as Lenore White Devin Harjes as Jack Dempsey Christina Jackson as Maybelle White Rege Lewis as Travis Elkins Solomon Shiv as Herman "Chayem" Kaufman Ty Michael Robinson as Samuel Crawford Skai Jackson as Adeline White DeWanda Wise as Henny Walker Tyrone Mitchell Henderson as Wilfred Linda Thompson Williams as Widow #2 Megan Sikora as Philadelphia prostitute's madam Marilyn Berry as Mrs Mayhew Sidné Anderson as Bereaved mother Nneoma Nkuku as Widow #3