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 Paul Ben-Victor as Jack Dragna Ernie Hudson as Bunny Amin Joseph as Skeety Geoffrey Blake as Assistant D.A. Lloyd Reese Yorgo Constantine as Ace Stephen Bishop as Smooth Watson Jack Conley as Jack O'Mara Emily Baldoni as Claire Harmony Frankie Jay Allison as Banana Louie John Cirigliano as Old Gent Co Starring Edward Edwards as Blake Cremmins Kylie Rogers as Peggy O'Donnell Dornell Harris as Poppy Gary Kraus as Cop #4 Robert Craighead as Barney William Christopher Stephens as Bookie #2 Matt Orduna as Bookie #1 Peter Navy Tuiasosopo as Big Oso