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