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Wittman’s first air race was in Milwaukee, Wisconsin in 1926 in which he placed second. Wittman’s first race plane was constructed in 1931 and made its debut at the National Air Races in Cleveland that year. It was initially powered by an American Cirrus engine. Each winter Wittman would rebuild the 'Chief', and over the years the refinements added significantly greater performance.
In 1934, Steve decided to go for the 'big time' and build a race plane capable of winning the Thompson Trophy. Wittman’s design philosophy emphasized light weight over streamlining, and 'Bonzo' took this approach to its extreme, being dubbed the 'flying barn door' by the press due to its angular appearance. Nonetheless, 'Bonzo's excellent performance made Steve one of the top contenders for the Thompson Trophy. Wittman’s first race in 'Bonzo' was the 1935 Thompson Trophy race, in which he placed second behind Harold Neumann in 'Mr. Mulligan'.
For 1936, Wittman rebuilt 'Bonzo', installing a new landing gear. Since the National Air Races were in Los Angeles that year, he had a long cross-country flight to reach Los Angeles. After landing at Cheyenne, Wyoming, an engine backfire caused 'Bonzo' to catch on fire; the fire was extinguished before 'Bonzo' was completely destroyed. But the damage was too great to be repaired for any further racing that year.
1937 turned out to be Wittman’s most successful year. 'Bonzo' was the fastest qualifier for the Thompson Trophy race, and he led for the first 18 laps of the 20 lap race. With a huge lead and the race seemingly in the bag, the engine began to run rough, and Wittman was forced to throttle back to remain in the race, finishing in 5th place. At the 1938 National Air Races, Wittman placed 3rd in the Thompson Trophy race in 'Bonzo', and in 1939 Wittman placed 5th after cutting a pylon at the race start.
Wittman remained active in aviation his entire life. On April 27, 1995, Wittman and his wife took off for a routine cross-country flight from Ocala, Florida to their summer home in Oshkosh, Wisconsin. The Wittman "O&O" crashed five miles south of Stevenson Alabama, killing both Wittman and his wife Paula.