Guest Stars Jayme Lawson as Young Michelle Michael Potts as Fraser Robinson Kristine Frøseth as Young Betty Eliza Scanlen as Young Eleanor Geraldine Singer as Dorothea Warren James DuMont as Herpolsheimer's Manager Co Starring Darius Ledbetter as Craig Robinson Jeremy Bobb as Theodore Roosevelt Charlie Plummer as Young Franklin Delano Roosevelt Jake Picking as Young Gerald Ford Lauren Halperin as Receptionist Thomas E. Sullivan as Bill Warren Karen Beyer as Law Office Receptionist Paprika Steen as Hortense Bloomer Barbara Rosenblat as Madame Souvestre Roxzane T. Mims as Church Meeting Guest 1 Morgane Bensadoun as Jane Crosby Fitzgerald as Carol Cole Paulson as Young Franklin's Friend Adeleine Whittle as Abigail Julian De Niro as Young Barack Obama Emma Faith as Emma Alexa Jennings as Lorraine Evelyn Kasper as Eloise Ava Love as Thérèse Lauren Searl as Elizabeth Gwen Waymon as Church Meeting Guest 2 Shannon Purser as Peg Kevin Sangston as Co-worker Eugene