In September 1930, Chester bought a Davis D-1-85 parasol, and flew it to victory in the National Air Races.[1] He later developed a series of successful air racers named after Popeye cartoon and comic strip characters. His designs were the Chester Jeep, Chester Goon, and Chester Swee Pea.[2] Chester's "Jeep" became a formidable racer.
He would tow his aircraft from race site to race site, driving a matching colored Auburn boat tailed Jeepster [3] Chester's "Jeepster" and "Goon" were powered by Menasco Motors Company engines, which he tuned for maximum performance and reliability. Al Menasco took note of Chester's engine building and tuning skills. In 1939 Chester was hired by Menasco as an engine designer to help develop the Menasco Pirate and Buccaneer inverted inline aircraft engines.
During World War II, Chester went to work for North American Aviation as an engineer employing his racing experience on new designs.[4]
Chester was the president of the Professional Race Pilots Association and early promoter of midget air racing, the forerunner to Formula One Air Racing.[5] Chester died when his V-tailed racer Swee Pea II crashed in the slipstream of other racers at a San Diego meet.[6] Chester had entered every National air race held since 1929 until his death.[7]
Chester was inducted into the Motorsports Hall of Fame of America in 2023.