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 Kathleen McCafferty as Press Secretary Curran Connor as Media Consultant Erica Chamblee as Cassandra Maury Ginsberg as Strategist 2 Prairie Griffith as Protester Marva Hicks as Strategist 1 Jan Johns as Associate Steve Lebens as Tilden's Assistant Peak Kwinarian as Deputy Chair Maureen Kerrigan as Strategist 3 Kevin Murray as Strategist 4 Jose Luis Munoz as Union Protester Michael McKenzie as Hotel Manager Kianné Muschett as Reporter Micheila Leighland as Gala VIP