Shore and the Bruins won their second Stanley Cup in 1939. Shore retired and bought the Springfield Indians of the American Hockey League, where he was player-owner in 1939–40. He was persuaded to rejoin the Bruins after injuries to the Bruins' defence corps, with an agreement that he would play in home games for $200 per match. Shore played just four games for Boston, and was reported as being unenthusiastic about the arrangement. Obtaining permission to play in the Indians' home games, he began to agitate to play in Springfield road games as well, which provoked his trade to the New York Americans on January 25, 1940, for Eddie Wiseman and $5000. He stayed with the Americans through their elimination from the playoffs, and was simultaneously playing with the Indians in their playoff games. Shore's final NHL game was March 24 against the Detroit Red Wings, which coincidentally was also the final NHL game for Hall of Famer and teammate Nels Stewart.