Guest Stars Lisa Rubin as Herself Charlie Sykes as Himself Peter Strzok as Himself John Heilemann as Himself Mara Gay as Herself Ben Rhodes as Himself Ian Bassin as Himself Matthew Dowd as Himself Amy McGrath as Herself Gerry Connolly as Himself Ayman Mohyeldin as Himself (Guest Host) Cindy McCain as Herself Jack McCain as Himself