Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself John Heilemann as Himself Katty Kay as Herself Eugene Robinson as Himself Lisa Rubin as Herself Keir Simmons as Himself Dave Aronberg as Himself James Stavridis as Himself Vaughn Hillyard as Himself Stephanie Ruhle as Herself Chuck Rosenberg as Himself Danny Cevallos as Himself Alexi McCammond as Herself Kristy Greenberg as Herself Anthony Scaramucci as Himself Cass Sunstein as Himself Greg Brower as Himself Alicia Keys as Herself James Comey as Himself Jesse Ehrenfeld as Himself (Dr. Jesse Ehrenfeld)