Philip D. Ross was a successful politician and newspaperman who worked hard to ensure that the early Stanley Cup challenges were of a high standard. No individual had more involvement with important decisions surrounding the Cup and the first Canadian amateur hockey leagues than Ross.
The native of Montreal was a fine all-round athlete. He captained the McGill University football team that played Harvard in 1876 and was a member of several Canadian rowing championship crews. Ross was also an excellent lacrosse player and the founder of several golf and country clubs. On the ice he played with two of Lord Stanley's sons on the Rideau Rebels team that did much to popularize the game in Ontario. It also drew the attention of his Lordship himself to the point that he commissioned the famous Cup bearing his name.
During this time Ross also moved around as a reporter and editor on the Montreal Star then the Toronto Mail. One of his assignments for the Montreal paper was to report from the Parliamentary press gallery. After moving to the nation's capital, he bought half the interest in the Ottawa Journal and became active in politics as an alderman.
After Lord Stanley donated the Cup bearing his name, he appointed Ross as one of its trustees. He was vigilant about preventing any abuses of the competition that could tarnish the image of the trophy. A few decent teams were turned down by Ross in this effort to ensure that each Stanley Cup challenge would be competitive and exciting.
Ross was also involved in the early days with the Ontario Hockey Association (OHA), playing on the Ottawa senior team, refereeing and representing the city on the executive.
He also served as a trustee of the prestigious Minto Cup of lacrosse and turned down the trusteeship of the Grey Cup. In all, Ross served as a trustee of the Cup for 56 years, right up to his death in 1949. He was inducted into the Hockey Hall of Fame posthumously, in 1976.