Guest Stars Anatol Yusef as Meyer Lansky Kevin O'Rourke as Mayor Edward Bader Victor Verhaeghe as Damien Fleming Heather Lind as Katy Ivo Nandi as Joe Masseria Stephen Root as Gaston Means Christopher McDonald as Harry Daugherty Patrick Kennedy as Dr. Douglas Mason Ed Jewett as Jess Smith Co Starring Brady Noon as Tommy Darmody Connor Noon as Tommy Darmody Declan McTigue as Teddy Schroeder Rory McTigue as Teddy Schroeder Chris Caldovino as Tonino Sandrelli Michael Zegen as Benjamin "Benny" Siegel Wrenn Schmidt as Julia Sagorsky Joseph Aniska as Agent Stan Sawicki Pearce Bunting as Bill McCoy Mark Borkowski as Paul Sagorsky Rebecca Luker as Sister Agnes Jack Ferry as Gareth Murray James Ciccone as Joe Masseria's thug Patrick Gallo as Franco Ray Crisara as Tall Cynthia Silver as Tourist Michael Thomas Walker as Fats
