When the Toronto Maple Leafs made Cliff Fletcher their new general manager, Fletcher made made a blockbuster trade with Calgary, where he had previously been general manager. He acquired "Killer" (a nickname given to Gilmour by a St. Louis teammate because of the fierce look in his eyes) as well as many other players that would help the Leafs and their Stanley Cup dreams.
After being named captain of the Maple Leafs, Gilmour started to soar. He helped the team to the playoffs taking down powerhouse Detroit Red Wings in the first best-of-seven series and went on to play his former team the Blues in the second round.
Everyone who saw the game remembers Doug's wraparound goal on Curtis Joseph where he kept going back and forth behind the net and finally slid it into the net behind a sprawling Joseph. That series was also a win for the Leafs as they headed on to the third round and eventually lost to Wayne Gretzky and the Los Angeles Kings.
After many more years as a Leaf and building a large fan base, Gilmour was traded by Fletcher to the Chicago Blackhawks. As luck would have it, Chicago was Toronto's opposition on the night of the last game in the historic Maple Leaf Gardens. Gilmour ended up scoring that game and in the closing ceremonies, Gilmour was given a standing ovation by the Toronto fans, showing that even though he had been traded, he was forever a Toronto Maple Leaf.
After being traded from Chicago to the New Jersey Devils, Gilmour was again traded to the Buffalo Sabres where he spent a couple of seasons. Then Gilmour, a well travelled player by this time, was traded to the Montreal Canadiens, the Maple Leafs' rivals. Gilmour had a good playoff run with the Canadiens but it was cut short by the Carolina Hurricanes in the second round.
Rumors floated around the hockey world that Gilmour wanted to finish his NHL career and he might be retiring. To the delight of Maple Leaf fans the NHL trade deadline of 2003 brought good news: the Maple Leafs had signed Gilmour so that he could finish his career in Toronto. Unfortunately, he suffered a knee injury in his first game back on March 13, and he officially announced his retirement on September 8, 2003.
Gilmour had 450 goals and 964 assists in 1474 games in his NHL career.