Guest Stars Dr. Jonathan Reiner as Himself Kaitlan Collins as Herself John Harwood as Himself Sanjay Gupta as Himself (Dr. Sanjay Gupta) Anthony Scaramucci as Himself Laura Coates as Herself Jim Messina as Himself Arlette Saenz as Herself Evan Perez as Himself Mary Trump as Herself Stuart Stevens as Himself Mark Preston as Himself Wesley Clark as Himself (Gen. Wesley Clark) Bob Casey as Himself (Sen. Bob Casey)