In 1942 Stewart was called from the minors to play in the Stanley Cup Finals, where he helped the Toronto Maple Leafs win the championship. The next season, Stewart won the 1943 Calder Trophy. He became the first player to win the Stanley Cup before the Calder. (See Danny Grant, Tony Esposito, and Ken Dryden). Gaye won his second Stanley Cup again with the Maple Leafs, in 1947. Over his career, Gaye Stewart played for five of the original six teams: Toronto, Chicago, Detroit, New York, and Montreal. He played 502 career NHL games, scoring 185 goals and 159 assists for 344 points. He led the NHL in goals with 37 during the 1945–46 season.