Guest Stars Charlie Cox as Owen Slater Rory McTigue as Teddy Schroeder Lucy Gallina as Emily Schroeder Victor Verhaeghe as Ward Boss Fleming Robert Clohessy as Jim Neary Kevin O'Rourke as Mayor Edward Bader Heather Lind as Katy Dominic Chianese as Leander Cephas Whitlock Christopher McDonald as Harry Daugherty Richard Easton as Jackson Parkhurst Co Starring Connor Noon as Tommy Darmody Adam Mucci as Deputy Halloran William Hill as Ward Boss O'Neill Edward McGinty as Alderman Al Boyd Jacqueline Pennewill as Lillian Brandon Zumsteg as Brian Thompson Peter Van Wagner as Isaac Ginsburg Ed Jewett as Jess Smith T.J. Kenneally as Charles Kenneth Thorogood AKA "Chip" Bill Camp as Glenmore Edmond Genest as Mr. Markham Jon DeVries as Pete Leslie Henstock as Hooker #1 Martin LaPlatney as Mr. Darlington Thomas Toner as Mr. Ennis Tom Morrissey as Mr. Webber Todd Davis as Alexander