Guest Stars Jonathan Lemire as Himself Andrew Ross Sorkin as Himself Mike Barnicle as Himself John Heilemann as Himself Molly Jong-Fast as Herself Claire McCaskill as Herself Donny Deutsch as Himself Peter Baker as Himself Symone Sanders-Townsend as Herself Chris Matthews as Himself Jonathan Martin as Himself Charlie Sykes as Himself Anand Giridharadas as Himself Lauren Leader as Herself Eddie Glaude as Himself Willie Geist as Himself Maura Healey as Herself (Gov. Maura Healey) David Plouffe as Himself Meridith McGraw as Herself Mickey Down as Himself Konrad Kay as Himself Myha'la Herrold as Herself David Daley as Himself
