Guest Stars Reuel Pendleton as Staffer Suzanne Savoy as Patricia Whittaker Daisy Tahan as Sarah Russo Ben Hyland as Kevin Russo Erin Fritch as Ashley Curran Connor as Media Consultant Kathleen McCafferty as Press Secretary Erica Chamblee as Cassandra Maury Ginsberg as Strategist 2 Marva Hicks as Strategist 1 Kevin Murray as Strategist 4 Jan Johns as Associate Steve Lebens as Tilden's Assistant Peak Kwinarian as Deputy Chair Maureen Kerrigan as Strategist 3 Jose Luis Munoz as Union Protester Prairie Griffith as Protester Michael McKenzie as Hotel Manager Kianné Muschett as Reporter Micheila Leighland as Gala VIP