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