Guest Stars Sanjay Gupta as Himself (Dr. Sanjay Gupta) Kaitlan Collins as Herself David Axelrod as Himself Randi Kaye as Herself Maggie Haberman as Herself Dr. Leana Wen as Herself Jeffrey Toobin as Himself Kathleen Sebelius as Herself Andrew McCabe as Himself Preet Bharara as Himself Val Demings as Herself Mazie Hirono as Herself (Sen. Mazie Hirono)