Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself Andrew Ross Sorkin as Himself Lisa Rubin as Herself John Heilemann as Himself Donny Deutsch as Himself Jennifer Palmieri as Herself Eugene Robinson as Himself David Ignatius as Himself Molly Jong-Fast as Herself Ali Vitali as Herself Symone Sanders-Townsend as Herself Eddie Glaude as Himself Stephanie Ruhle as Herself Jeh Johnson as Himself Jon Hamm as Himself Sarah Paulson as Herself Corey Stoll as Himself Michael Esper as Himself Jim Wallis as Themselves Colin Allred as Himself