Chester was instrumental in the development of the Menasco Pirate and Buccaneer inverted inline engines.
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.
[3] Chester's "Jeep" and "Goon" were powered by Menasco Motors Company engines, which he tuned for maximum performance and reliability.
During World War II, Chester went to work for North American Aviation as an engineer employing his racing experience on new designs.