 After competing in his first transcontinental air race from New York to Los Angeles in 1928, he attained a medical waiver on his eyesight and received his pilot's certificate soon after (signed by Orville Wright).He then went on to design, build and pilot his own aircraft, including "Chief Oshkosh" in 1931 and "Bonzo" in 1934.Wittman's first race in an aircraft design that was his was in "Bonzo", in the 1935 Thompson Trophy race, where he placed second.