Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself Al Sharpton as Himself Katty Kay as Herself Andrew Ross Sorkin as Himself Lisa Rubin as Herself John Heilemann as Himself Donny Deutsch as Himself Eugene Robinson as Himself Chuck Rosenberg as Himself James Stavridis as Himself Joyce Vance as Herself Chris Matthews as Himself Danny Cevallos as Himself Jon Meacham as Himself Barbara McQuade as Herself Andrew Weissmann as Himself Stephanie Ruhle as Herself Dan Goldman as Himself Michael Beschloss as Himself Neal Katyal as Himself Ari Melber as Himself Mitch Landrieu as Himself Katie Benner as Herself Jamie Raskin as Himself Jeffrey Rosen as Himself Douglas Brinkley as Himself