Raymond Earl McGregor (US 1937-38). This photo was taken about 1950 when he was presented with his 10 year pin as a Trans Canada Airlines pilot (later Air Canada). Presenter is Maurice McGregor, Ray's older brother (SM 1920s) who was then in charge of TCA Overseas Service.
Photo of a soldier, probably in WWI, an enlisted man and an old boy of US. Uniform suggests he is 1) an officer 2) from a Scottish or Canadian-Scottish Regiment and 3) a pilot (he has his 'wings' over left pocket, the Air Force was in its early infancy)