Guest Stars Hamish Linklater as Jeb Magruder Allison Tolman as Winzola "Winnie" McLendon J.C. MacKenzie as Howard Hunt Chris Bauer as James McCord Martha Kelly as Rose Mary Woods Anne Dudek as Diana Oweiss Carlos Valdés as Agent Paul Magallanes Nat Faxon as Bob Haldeman John Carroll Lynch as Acting Director L. Patrick Gray Chris Messina as Agent Angelo Lano 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 Korbin Marum as Raymond Liddy Forte Rodriguez as Marshall Edmund 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