The Calgary Flames didn’t just add Doug Gilmour in the fall of 1988 - they changed the shape of their championship run.
A year earlier, Calgary had finished atop the Smythe Division with 105 points, finishing ahead of the Montreal Canadiens for the NHL’s best record. But that strong regular season ran into a wall in the playoffs, where the Flames, two seasons removed from the Stanley Cup Final, were swept by the Edmonton Oilers in the Division Finals. Edmonton then went on to win the Cup, a result that marked the end of the Wayne Gretzky era in northern Alberta.
That setback pushed then general manager Cliff Fletcher to make a major move on September 6, 1988. Working the phones with the St.
Louis Blues, Fletcher landed four players who would become part of Calgary’s Stanley Cup-winning team in May 1989. The Flames sent Mike Bullard, Tim Corkey, and Craig Coxe to St.
Louis and received Steve Bozek, Michael Dark, Mark Hunter, and Doug Gilmour in return.
The deal kept evolving almost immediately. Within hours, Fletcher moved Bozek and Paul Reinhart to the Vancouver Canucks for a third-round pick in 1989, and that pick became Veli-Pekka Kautonen.
Gilmour’s numbers in Calgary were strong enough on their own. In parts of four seasons with the Flames, he scored 81 goals and 295 points in 266 games, which still places him 27th all-time in franchise history. By the time Calgary traded him to the Toronto Maple Leafs on January 2, 1992, he had already piled up the 13th-most assists in team history.
That later trade with Toronto was a monster, the biggest in Flames history by volume. Ten skaters changed teams in a move that saw recently hired general manager Doug Risebrough send Gilmour, Jamie Macoun, Kent Manderville, Ric Nattress, and goalie Rick Wamsley to the Maple Leafs in exchange for Craig Berube, Alexander Godynyuk, Gary Leeman, Michel Petit, and goalie Jeff Reese.
Gilmour’s best individual years after that came in Toronto, where he led the Maple Leafs to the Western Conference Final in 1993 and 1994. Those runs were the franchise’s first Final Four appearances since 1967, and the 1993 Game 7 loss to Gretzky and the Los Angeles Kings is still one of the NHL’s most memorable playoff moments. Gilmour was inducted into the Hockey Hall of Fame in 2011.
He didn’t duplicate his St. Louis output in Calgary, but the trade still paid off exactly where it mattered most. Gilmour became one of the key pieces behind the Flames’ only Stanley Cup championship, and the move stands as one of the sharpest in Fletcher’s Hall of Fame career.
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