
2. Doug Gilmour
Doug Gilmour joined the Toronto Maple Leafs in an epic trade that echoed the aforementioned player swap that brought Max Bentley to the Buds in 1947.
It was the early 1990s and the Toronto Maple Leafs were still reeling from the destruction wrought by owner Harold Ballard and general manager Punch Imlach twelve years earlier. Imlach, with Ballard’s blessing, had traded Lanny McDonald, Tiger Williams, Pat Boutette, Darryl Sittler and Ian Turnbull and left the franchise in shambles.
By Christmas of 1991, a new GM, Cliff Fletcher, had inherited this mess, but he was about to receive a franchise reviving gift from Calgary, the team he had just left, in the form of Gilmour.
As Fletcher knew, Doug Gilmour had always been a great two-way NHL centre. However, on a deep Flames roster Gilmour was a number two pivot to Joe Nieuwendyk. If Fletcher could package off Gary Leeman with an assorted collection of odds and ends and dangle them in front of his young replacement as Flames GM, Doug Risebrough, he might just be able to wrest Gilmour from the Flames.
On January 2, 1992, just a few days after Christmas, the Toronto Maple Leafs received one the greatest belated Christmas presents in NHL history-Doug “Killer” Gilmour.
In the biggest trade in league history, Leeman, Craig Berube, Jeff Reese, Alexander Godynyuk, and Michel Petit went to Calgary, while Gilmour, Jamie Macoun, Rick Natress, Rick Wamsley, and Kent Manderville came to the Big Smoke.
Maple Leaf fortunes turned immediately.
Yes, Virginia. There is a Santa Claus. He lives in Calgary and calls himself Doug Risebrough.