Guest Stars Jonathan Lemire as Himself Mike Barnicle as Himself Katty Kay as Herself Peter Baker as Himself Chris Matthews as Himself Jacqueline Alemany as Herself Mara Gay as Herself Huma Abedin as Herself Maggie McGrath as Herself George Conway as Himself Jaime Harrison as Himself Jeremy Bash as Himself Chris Coons as Himself (Sen. Chris Coons) J. Michael Luttig as Himself Amy Walter as Herself Jake Sullivan as Himself Julia Ioffe as Herself Barbara Comstock as Herself Raj M. Shah as Himself Christopher Kirchhoff as Himself