Shaped the urban cityscape of Honolulu, Hawaii. His comments following the Massie Trial of 1933 were controversial enough to thrust him into the vortex of public opinion. He designed what eventually became La Pietra, the private all-girls academy.
He worked early in his career for the Hawaiian Dredging Company. Among his first tasks was the carving out of a dry dock at the site that would become the Pearl Harbor naval base. He was contracted by the U.S. Army Motor Transport Corps as World War I raged.
His dredging company helped to build the canal that opened Waikiki to commercial development.
He was born in Honolulu, which was then part of the Kingdom of Hawaii. His father, Benjamin Dillingham, was the founder of the Oahu Railway and Land Company. His mother, Emma Louise Smith, was missionary Lowell Smith's daughter. He married Louise Olga Gaylord in 1910.
His son entered Hawaiian politics, challenging Daniel Inouye for a 1962 seat in the Senate.