Guest Stars Jonathan Lemire as Himself Andrew Ross Sorkin as Himself Mike Barnicle as Himself Al Sharpton as Himself (Rev. Al Sharpton) John Heilemann as Himself Katty Kay as Herself Eugene Robinson as Himself David Ignatius as Himself Claire McCaskill as Herself Donny Deutsch as Himself Chris Matthews as Himself Jon Meacham as Himself Jonathan Martin as Himself Stephanie Ruhle as Herself Jim Messina as Himself Hakeem Jeffries as Himself (Rep. Hakeem Jeffries) J.B. Pritzker as Himself (Gov. J.B. Pritzker) Alejandro Mayorkas as Himself Jasmine Wright as Herself David Plouffe as Himself
