Doug Gilmour (Calgary Flames)

He arrived from Calgary and paid immediate dividends, helping the Flames to the Finals and scoring the Stanley Cup-winning goal against Montreal. Gilmour was acquired by the Maple Leafs in February 1992, and set a Toronto record for points in a single season (127) the following year. In 1994, Gilmour was honored with the “C” on his jersey as Toronto’s new captain.