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