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

He had worked in the 1920s with Mark Stump at Launceston Grammar School, and after Les Trewin’s employment at Geelong Grammar School and The Geelong College, Mark Stump encouraged his appointment to Carey’s staff during the Great Depression when work was exceptionally difficult to find. Always bedecked in a blue suit and blue shirt, Les Trewin carried out his duties loyally and became a central figure in boarders’ lives. ‘He knew everything we were about to do before we did it’, recalled boarder Ray Reed (OCG 1949). 

His wall was covered in pencilled notes which created an accounting system for boarders’ pocket money, of which he was in charge. Although he sometimes caned boys for serious misdemeanours, he was well liked and had a great sense of humour.

Despite a lack of any formal qualifications, Les Trewin was an accomplished teacher of Geography and led enjoyable excursions. He died in 1952, soon after the boarding house closed.