His predecessor, James Cuno, had previously headed the Courtauld Institute, the Harvard University Art Museums, the Hood Museum of Art, and the Grunwald Center for the Graphic Arts.
Woodruff was 38 when he received the Talladega commission. (Born in 1900 in Ohio, and raised in Tennessee, he died in 1980 in New York, where he taught at New York University for more than 20 years.) After studying at the John Herron Art Institute, Indianapolis, Woodruff broadened his experience at the Art Institute of Chicago's school, Harvard's Fogg Museum School, and in Paris between 1927 and 1931.
Caroline Kennedy has spent most of her life in the city, working there after graduating from Harvard, meeting her husband, Edwin Schlossberg, on the job at the Metropolitan Museum of Art and attending Columbia Law School there.