Guest Stars Daniel Roebuck as Nick Bledsoe Andrew Rothenberg as Eddy Sanderson Dana Gould as Tug Purcell John Pollono as Pat Dolan Michael McGrady as Chief Clemance Horall Richard Brake as Terry Mike Hagerty as Fat Jack Bray Gordon Clapp as Carl Steckler Louis Lombardi as Stucky Fein James Landry Hébert as Miles Hewitt Ernie Hudson as Bunny Paul Ben-Victor as Jack Dragna Amin Joseph as Skeety Geoffrey Blake as Assistant D.A. Lloyd Reese Yorgo Constantine as Ace Jack Conley as Jack O'Mara Stephen Bishop as Smooth Watson Emily Baldoni as Claire Harmony John Cirigliano as Old Gent Frankie Jay Allison as Banana Louie Co Starring Edward Edwards as Blake Cremmins Kylie Rogers as Peggy O'Donnell Dornell Harris as Poppy Robert Craighead as Barney Gary Kraus as Cop #4 William Christopher Stephens as Bookie #2 Matt Orduna as Bookie #1 Peter Navy Tuiasosopo as Big Oso