Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself Andrew Ross Sorkin as Himself John Heilemann as Himself Jennifer Palmieri as Herself Chuck Rosenberg as Himself Steve Rattner as Himself Joyce Vance as Herself Pablo Torre as Himself Dave Aronberg as Himself Mara Gay as Herself Symone Sanders-Townsend as Herself Eddie Glaude as Himself Julie Tsirkin as Herself Anand Giridharadas as Himself Stephanie Ruhle as Herself Michael Tomasky as Himself Tom Nichols as Himself Dasha Burns as Herself Lindsay Zoladz as Herself Anton Ptushkin as Himself