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 Anne Dudek as Diana Oweiss Chris Messina as Agent Angelo Lano John Carroll Lynch as Acting Director L. Patrick Gray Carlos Valdés as Agent Paul Magallanes Nat Faxon as Bob Haldeman Patton Oswalt as Chuck Colson Kat Foster as Barbara Walters John Ventimiglia as Judge John Sirica Nelson Franklin as Dick Moore Chris Conner as John Ehrlichman Adam Ray as Ron Ziegler Vincent Di Paolo as Vito Reed Diamond as Mark Felt Johnny Berchtold as Jay Jennings Virginia Gardner as Sharon Beth Hall as Helen Thomas Beth Malone as Maria Ahna O'Reilly as Gail Magruder 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 Korbin Marum as Raymond Liddy Angela Sprinkle as Tour Guide Aaron Goddard as Tom Snyder Amelia Gray as Feminist #1 River Drosche as James Liddy Benjamin Mackey as Tom Liddy Michael Paul King as Mike Douglas Aubree Bowen as Other Parent Christopher Mychael Watson as Chubby Checker Kenneth Hodges as Robert Jordan Hendricks as Young Republican Dominic Daniel as Bernard Shaw Alan Heitz as Crew Cut & Glasses Pat Asanti as Grumpy Gus Ericka Kreutz as Frances Liddy Lisa Carswell as Haldeman's Secretary Jay Jackson as Robert