Guest Stars Jonathan Lemire as Himself Al Sharpton as Himself Katty Kay as Herself David Ignatius as Himself Claire McCaskill as Herself Keir Simmons as Himself Pablo Torre as Himself Raf Sanchez as Himself Dominic Chu as Himself John Kirby as Himself Tom Winter as Himself Yasmeen Abutaleb as Herself Paul Finebaum as Himself Daniela Pierre-Bravo as Herself Mark Regev as Himself Michael S. Schmidt as Himself A.V. Rockwell as Herself Peter Wehner as Himself Lena Waithe as Herself