Guest Stars Jonathan Lemire as Himself Richard Haass as Himself Molly Jong-Fast as Herself Claire McCaskill as Herself James Stavridis as Himself Ali Vitali as Herself Andrew Weissmann as Himself Barbara McQuade as Herself Dominic Chu as Himself Anne Applebaum as Herself Julia Ainsley as Herself Ben Smith as Himself Elissa Slotkin as Herself Monica Alba as Herself Édgar Ramírez as Himself (Edgar Ramirez) Hallie Jackson as Herself Mark Bowden as Himself