Toronto Maple Leafs Syl Apps + Conn Smythe Photo NHL Hockey Stanley Cup HOFToronto Maple Leafs Syl Apps + Conn Smythe Photo NHL Hockey Stanley Cup HOF Syl was a Canadian professional ice hockey player for the Toronto Maple Leafs from 1936 1948 and Olympic pole vaulter. Apps won the Stanley Cup champion in 1942, 1947, and 1948 and was inducted into the Hockey Hall of Fame in 1961. Smythe was a Canadian businessman and sportsman in ice hockey and horse racing. Best known as the principal owner of the Toronto Maple Leafs of the