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 Peter Van Wagner as Isaac Ginsburg Pearce Bunting as Bill McCoy Michael Zegen as Benjamin Siegel Bill Sage as Solomon Bishop John Keating as Ernie Moran Amy Warren as Pauleen Franklin Ojeda Smith as Deacon Lemuel Cuffy Natalie Wachen as Lenore White Justiin A. Davis as Lester White Joel Brady as Agent Clarkson Devin Harjes as Jack Dempsey Christina Jackson as Maybelle White Solomon Shiv as Herman "Chayem" Kaufman Rege Lewis as Travis Elkins Ty Michael Robinson as Samuel Crawford DeWanda Wise as Henny Walker Skai Jackson as Adeline White 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