Eleanor Roosevelt and “Chief” Charles Alfred Anderson in 1941. Roosevelt convinced the Rosenwald Fund to expand the pilot training program at Tuskegee. Early in the year, Roosevelt visited the Tuskegee Institute's Moton Airfield, asking the chief flight instructor, "Chief" Charles A. Anderson, if he would take her flying. Despite extreme objections from the Secret Service, Roosevelt spent more than an hour flying over the Tuskegee airfield, which was possibly the first time a black man had ever flown a plane with a white woman as his passenger. (Air Force Historical Research Agency photo) Source: U.S. Air Force .