Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself Andrew Ross Sorkin as Himself John Heilemann as Himself Claire McCaskill as Herself Jacqueline Alemany as Herself Keir Simmons as Himself Adrienne Elrod as Herself Mara Gay as Herself Eddie Glaude as Himself George Conway as Himself Dan Goldman as Himself Doris Kearns Goodwin as Herself Chris Murphy as Himself Josh Shapiro as Himself Ruben Gallego as Himself Alex Edelman as Himself