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Tom Lawson is an alumnus of Trinity College School, class of 1947. He worked at TCS from 1955 to 1988 as an English teacher. During that time he served as the Ketchum Housemaster and from 1978 to 1988 as the Head of the English Department. He was also founder of the Social Services Corps, and a great advocate of student debates. He received his B.A. from the University of Toronto, his M.A. from King's College, Cambridge and his Ontario Teacher's Certificate. Presently, Lawson is an honorary trustee at TCS.

John D. Burns worked at TCS from 1943 to 1987 as Bickle Housemaster, a History teacher and an Archivist. He completed his undergrad at the University of Toronto and received his Ontario Teacher's Certificate from the Normal School in Toronto. He began working as the School archivist in 1984. He passed away in 1987. In 2005 Trinity College School's Archives were named in his honour.

Peter Kedwell worked at TCS from 1975 to 2010 as a Modern Languages teacher. He served as the Head of the Modern Languages department, a member of the Guidance department and the Brent House Housemaster from 1981 to 1982. He received his B.A. from Huron University College and his B.Ed. from the University of Western Ontario. Upon his retirement he was awarded the Toronto Branch Medal and in 2012 received the Queen's Diamond Jubilee Medal. in 2017 he became a TCS trustee.

Tony Prower is an alumnus of Trinity College School, class of 1946. He was a music master at Trinity College School from 1951-1991. While at TCS, Prower was head of the Glee Club, the Music Club, music director of the Dramatics Club, and coached Middleside Football. Presently, Prower serves as an Honorary Trustee at TCS.

Jack Goering was born February 16, 1925 in Barcelona, Spain. A TCS alumnus, he attended the school from 1941-1943. Inn his graduating year he served as a prefect and won the Grand Challenge Cup. He received his B.A.Sc. in Engineering from the University of Toronto and his Ontario Teachers Certificate. Jack Goering worked at TCS from 1961 to 1985 as a Science teacher. He was a proud advocate of sustainable living and co-founded the Ganaraska Hiking Trail in Port Hope, Ontario with Pat Lawson.