Guest Stars Jonathan Lemire as Himself Andrew Ross Sorkin as Himself Lisa Rubin as Herself Eugene Robinson as Himself Claire McCaskill as Herself Elise Jordan as Herself Vaughn Hillyard as Himself Danny Cevallos as Himself Andrew Weissmann as Himself Mara Gay as Herself Symone Sanders-Townsend as Herself Julie Tsirkin as Herself Charles F. Coleman Jr. as Himself Ankush Khardori as Himself Kristen Welker as Herself Prentice Penny as Himself Illia Ponomarenko as Himself John Kasich as Himself Ali Velshi as Himself Joanna Coles as Herself Edward F. O'Keefe as Himself