Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself Andrew Ross Sorkin as Himself Richard Haass as Himself Donny Deutsch as Himself Chuck Rosenberg as Himself James Stavridis as Himself Jacqueline Alemany as Herself Steve Rattner as Himself Keir Simmons as Himself Barbara McQuade as Herself Symone Sanders-Townsend as Herself Jen Psaki as Herself George Conway as Himself Anand Giridharadas as Himself Maggie McGrath as Herself Huma Abedin as Herself Christopher Krebs as Himself Neal Katyal as Himself Ari Melber as Himself Tim Miller as Himself J. Michael Luttig as Himself Jeffrey Rosen as Himself Mary B. McCord as Herself