Les Trewin (staff 1933–51), Harold Steele’s first cousin, succeeded Stuart Hickman as resident master in charge of the boarding house and also taught the Senior Entrance class, an additional year between the Preparatory School and Form 1 of the Senior School.

Trewin had worked alongside Mark Stump at Launceston Grammar School during the 1920s. Following periods of employment at Geelong Grammar School and The Geelong College, he was encouraged by Stump to apply for a position at Carey during the Great Depression, when teaching opportunities were scarce.

Always impeccably dressed in a blue suit and blue shirt, Trewin became a central figure in the lives of Carey’s boarders. Former boarder Ray Reed (OCG 1949) later recalled that ‘he knew everything we were about to do before we did it’.

Trewin managed the boarders’ pocket money through a meticulous accounting system recorded in pencil on his office wall. He was widely respected, well-liked and remembered for his dry wit and sense of humour.

An accomplished Geography teacher, Trewin was known for leading engaging excursions that brought learning to life beyond the classroom. Victorian teacher registration records confirm that he was registered with the Education Department (Roll No. 489), indicating that he held formal teaching credentials. His loyal service to Carey spanned nearly two decades, and his influence on generations of boarders and students was considerable. He died in 1952, shortly after the closure of the boarding house.