Guest Stars Jonathan Lemire as Himself Al Sharpton as Himself Eugene Robinson as Himself Steve Rattner as Himself Chris Matthews as Himself Keir Simmons as Himself Andrew Weissmann as Himself Symone Sanders-Townsend as Herself Jonathan Martin as Himself Julie Tsirkin as Herself Amanda Carpenter as Herself David Holt as Himself (Mayor David Holt) Kaylee Hartung as Herself Quinton Lucas as Himself (Mayor Quinton Lucas) Dan Webb as Himself Ben Chavis as Himself (Benjamin F. Chavis)