He received a Bachelor of Science degree in engineering from the Massachusetts Institute of Technology in 1902.
[4] MacNaughton's designs at this time include the Sellwood Branch YMCA and the Blake McFall Company Building.
He is credited with designing the 1906 Alexandra Apartment/Hotel building on NW 21st Place in Portland,[2] although a set of architectural drawings for the building was found among the Lawrence papers, leading researchers to conclude that the design credit should go to Lawrence.
Part of the building collapsed during the renovation, and MacNaughton was fired by owner Henry Pittock.
Among the surviving designs of MacNaughton, Raymond, and Lawrence are the Samuel G. Reed House and the Cumberland Apartments.
Lawrence left the firm in 1910 to start his own company, and the two remaining partners continued as MacNaughton and Raymond.
In 1919 Portland mayor George Luis Baker appointed MacNaughton to the newly created planning commission.
[10] The firm also handled stock investments, and when the Portland Public Market was approved in the 1920s, Strong and MacNaughton was the transfer agent.
[15] MacNaughton served for a time as an associate professor of banking at the Stanford Graduate School of Business.
The company was purchased for $5.6 million by Samuel Irving Newhouse, Sr. in 1950, and MacNaughton's tenure ended.
He raised faculty salaries, created a scholarship fund for students, and increased the size of Reed's endowment through donations.