Guest Stars Allison Tolman as Winzola "Winnie" McLendon Hamish Linklater as Jeb Magruder Chris Bauer as James McCord J.C. MacKenzie as Howard Hunt Martha Kelly as Rose Mary Woods Nat Faxon as Bob Haldeman Chris Messina as Agent Angelo Lano John Carroll Lynch as Acting Director L. Patrick Gray Carlos Valdés as Agent Paul Magallanes John Ventimiglia as Judge John Sirica Nelson Franklin as Dick Moore Vincent Di Paolo as Vito Erinn Hayes as Peggy Ebbitt Marin Ireland as Judy Hoback Reed Diamond as Mark Felt Billy Smith as Ken Ebbitt Matt Malloy as Kenneth H. Dahlberg Co Starring Scott Michael Morgan as Bernard Barker Oscar Torre as Virgilio Gonzalez Jordi Caballero as Eugenio Martinez Don DiPetta as Frank Sturgis Danny Winn as Nixon Forte Rodriguez as Marshall Edmund Andrew Patrick Ralston as Le Cirque Diner 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 Sean Persaud as Lawyer 2 Ian Gary as Reporter #2 Matt Kaminsky as Lawyer 1 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