Guest Stars Clea DuVall as Malvina "Tommy" Thompson Jayme Lawson as Young Michelle Cailee Spaeny as Anna Eleanor Roosevelt Michael Potts as Fraser Robinson Ellen Burstyn as Sara Delano Roosevelt Saniyya Sidney as Sasha Obama Lexi Underwood as Malia Obama Gloria Reuben as Valerie Jarrett Co Starring Evan Parke as Secret Service Agent Allen Taylor Eryn Rea as Gayle Ford Kelvin John Davis as Wilson Roosevelt Jerman Marc Hills as Jack Ford Ben Cook as Steven Ford Cayden Boyd as Michael Ford Darius Ledbetter as Craig Robinson John Connor as Radio Operator Maria Dizzia as Lucy Mercer Michael Shenefelt as James Roosevelt Gwendolyn Ellis as Martha Gellhorn Patrice Johnson as Clara Powell Ashley LeConte Campbell as Nicky Firestone Mark Zeisler as Leonard Firestone Larry Herring as Secret Service Agent Bruce Darin Toonder as Potential Donor Chris McKinney as Dean Stewart Jim Gleason as Donor John Kelsey Scott as Erica Ryan Jamaal Swain as Johnny Wright Jennifer Pierce Mathus as Jennifer Jordan Patrick as Jacob Morewitz Susan Willis as Elizabeth Dole Daniel Gerroll as Ambassador Ronald Lindsay Max Beard as Patrick Malin Bethany Geaber as Mrs. Malin Brooke Owens as May Lindsay Le Titia Sloan as Santita Jackson Larry Coulter as Bob Dole Michaela-Jolie Gilliard as Stewart Daughter Susan Lamb as Event Donor Linus Lamar as White House Waiter Douglas G. Bertolini as Joe Garagiola Ellis Hobbs IV as Stewart Son Gina Daniels as Velma Stewart Kate MacCluggage as Mrs. Michaelson Cody Land Pressley as David Kennerly Kelly O'Neal as Mrs. Lindsay