He first entered politics in 1970, winning election as a school trustee on the Toronto Board of Education.[1] He served as chair of the board in 1975 and 1976.[1]
He retired from elected politics in 1982 to accept a job as president of the Toronto chapter of the United Way,[1] and was succeeded in the 1982 municipal election by Joanne Campbell.[2] At the time of the election, Campbell was an executive assistant in Cressy's office; she later married Cressy in 1983.
His son Joe Cressy was elected to Toronto City Council in the 2014 municipal election. Gordon Cressy served on mayor-elect John Tory's transition team following the 2014 election.[5]
In 1994, the University of Toronto Alumni Association established the Gordon Cressy Student Leadership Awards in his honour "to recognize students who have made outstanding extra-curricular contributions to their college, faculty or school, or to the university as a whole."[7]