Guest Stars Allison Tolman as Winzola "Winnie" McLendon Hamish Linklater as Jeb Magruder J.C. MacKenzie as Howard Hunt Martha Kelly as Rose Mary Woods Chris Bauer as James McCord John Carroll Lynch as Acting Director L. Patrick Gray Nat Faxon as Bob Haldeman Chris Messina as Agent Angelo Lano Carlos Valdés as Agent Paul Magallanes Nelson Franklin as Dick Moore John Ventimiglia as Judge John Sirica Vincent Di Paolo as Vito Reed Diamond as Mark Felt Marin Ireland as Judy Hoback Erinn Hayes as Peggy Ebbitt Billy Smith as Ken Ebbitt Matt Malloy as Kenneth H. Dahlberg Co Starring Scott Michael Morgan as Bernard Barker Jordi Caballero as Eugenio Martinez Oscar Torre as Virgilio Gonzalez Don DiPetta as Frank Sturgis Danny Winn as Nixon Forte Rodriguez as Marshall Edmund Shannon Dee as Shore Club Couple #3 Andrew Patrick Ralston as Le Cirque Diner 2 Max Pescherine as Shore Club Couple #2 Christopher Sanders as Bouncer Jenny Tran as Anna Chennault John Combs as Doctor Feldman Alex Ball as Alexander Butterfield Ian Gary as Reporter #2 Matt Kaminsky as Lawyer 1 Sean Persaud as Lawyer 2 Doug Hurley as Field Officer Erin Marie Hogan as Shore Club Couple #1 Dominique Generaux as Reporter #1 Sarah Elizabeth Jensen as Candy Cinda Adams as Mo's Mother Rich Skidmore as Shore Club Couple #4