Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself John Heilemann as Himself Donny Deutsch as Himself Jennifer Palmieri as Herself Claire McCaskill as Herself Steve Rattner as Himself Ali Vitali as Herself Eddie Glaude as Himself Steve Kornacki as Himself Dominic Chu as Himself Wes Moore as Himself Ben Smith as Himself John Avlon as Himself James Carville as Himself Josh Stein as Himself