Guest Stars Delaney Williams as Sgt. Jay Landsman Michael K. Williams as Omar Little Robert F. Chew as Joseph "Proposition Joe" Stewart Isiah Whitlock Jr. as State Sen. R. Clayton "Clay" Davis Michael Kostroff as Maurice "Maury" Levy Michael Salconi as Det. Michael Santangelo Melanie Nicholls-King as Cheryl Richard DeAngelis as Ray Foerster Michael B. Jordan as Wallace Edward T. Norris as Det. Edward Norris Callie Thorne as Elena McNulty Shamyl Brown as Donette Wendy Grantham as Shardene Innes Steve Earle as Walon Clayton LeBouef as Wendell "Orlando" Blocker Chris Clanton as Savino Christopher Glenn Wilson as DEA Agent Aaron Michael Lacey as Maryland State Trooper M. Neko Parham as State Police Undercover Troy Wiggins Co Starring Domenick Lombardozzi as Det. Thomas "Herc" Hauk Clarke Peters as Det. Lester Freamon Seth Gilliam as Det. Ellis Carver Jim True-Frost as Det. Roland "Prez" Pryzbylewski Corey Parker Robinson as Det. Leander Sydnor Peter Gerety as Judge Daniel Phelan