Late in the 1932–33 season, he was hired as coach of the Chicago Black Hawks and became general manager as well the following season, building a defensive squad around Lionel Conacher and goalie Charlie Gardiner. He took the team from last place in their division in 1932–33 to their first Stanley Cup victory in 1934—despite scoring the fewest goals of any NHL team. Ten days after the Cup victory, Gorman resigned after a dispute with the owner. He went to Montreal as their manager-coach and helped the Montreal Maroons to their final Cup in 1935, thus becoming the first (and only) coach to win consecutive Stanley Cups with different teams. Gorman coached the Maroons until the club folded in 1938. In 1940, he became general manager of the Montreal Canadiens and led them to Cup victories in 1944 and 1946. He is the only person to manage four different teams to championships: the Senators, Black Hawks, Maroons and Canadiens. No other General Manager in the history of the NHL, Major League Baseball, the National Football League, or the National Basketball Association has won championships with four different teams.