The “Keep Us Flying” War Bonds poster was created in 1943, and the image of airman Diez was done by Betsy Graves Reyneau, a white artist who painted portraits of many prominent African Americans. A collection of portraits by Reyneau and African American artist Laura Wheeler Waring was commissioned in the 1940s by the Harmon Foundation and mounted in a traveling exhibition.
Robert Deiz was at the training field in 1943 when Reyneau came to Tuskegee for a sitting with scientist George Washington Carver. She had also been commissioned to come up with an image for the poster. He asked Reyneau if he could watch her as she painted. He had an interest in art, having studied it and having taught painting and sculpture in adult education classes in Portland. She chose him as the poster model after getting the OK from his commanding officer (who likely was Davis).
That poster was apparently not the only one featuring Tuskegee Airmen but perhaps the most recognizable. Another shows an airman standing on the wing of a plan with text urging folks to buy bonds during a fifth war bonds drive from June 12 to July 8 (1944). These drives were an all-out government effort using posters, radio and newspapers, entertainers and films to get folks to buy war bonds.