Guest Stars Jonathan Lemire as Himself Al Sharpton as Himself Richard Haass as Himself John Heilemann as Himself Donny Deutsch as Himself Jennifer Palmieri as Herself Eugene Robinson as Himself Steve Rattner as Himself Mara Gay as Herself Jen Psaki as Herself Anand Giridharadas as Himself Stephanie Ruhle as Herself Michael Beschloss as Himself Nancy Pelosi as Herself Mitch Landrieu as Himself Chuck Schumer as Himself Tim Kaine as Himself Carlos Curbelo as Himself John Chell as Himself (Chief John Chell) Janet Yellen as Herself Pete Aguilar as Himself Elizabeth Carr as Herself Dick Gephardt as Himself