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