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 Cayden Boyd as Michael Ford Ben Cook as Steven Ford Marc Hills as Jack Ford Kelvin John Davis as Wilson Roosevelt Jerman Eryn Rea as Gayle Ford John Connor as Radio Operator Darius Ledbetter as Craig Robinson Maria Dizzia as Lucy Mercer Gwendolyn Ellis as Martha Gellhorn Patrice Johnson as Clara Powell 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 Kelsey Scott as Erica Darin Toonder as Potential Donor Jim Gleason as Donor John Ryan Jamaal Swain as Johnny Wright Jordan Patrick as Jacob Morewitz Jennifer Pierce Mathus as Jennifer Kate MacCluggage as Mrs. Michaelson Bethany Geaber as Mrs. Malin Daniel Gerroll as Ambassador Ronald Lindsay Susan Willis as Elizabeth Dole Max Beard as Patrick Malin Kelly O'Neal as Mrs. Lindsay Cody Land Pressley as David Kennerly Douglas G. Bertolini as Joe Garagiola Larry Coulter as Bob Dole Susan Lamb as Event Donor Michaela-Jolie Gilliard as Stewart Daughter Linus Lamar as White House Waiter Brooke Owens as May Lindsay Le Titia Sloan as Santita Jackson Ellis Hobbs IV as Stewart Son Gina Daniels as Velma Stewart