Saturday, November 19, 2022

NHL99: Doug Gilmour and how the biggest trade in NHL history turned him into a superstar

Your team is about to make a trade. A big one. And not just one of those standard-issue rental deals we see so much of these days, in which only one team is really trying to improve while the other is kicking the can down the road. No, this is two teams that are both trying to get better, right now, and carefully exchanging pieces to try to make it happen.

How do you want the trade to work out?

If you’re feeling polite, you might say that you hope it ends up being a win for both teams. You’ll miss the players who are heading the other way, and you wish them nothing but the best. Trading doesn’t have to be a zero-sum game, you might remind yourself, and a good one can work out just fine for both teams. You would tell yourself that because you’re a good person.

You would be lying. You don’t want that at all.

No, you want the trade to be so lopsided that it feels unfair. You want to read about it on those “biggest heist in sports history” lists for decades to come. You want everyone your team dealt away to turn into a pumpkin. And somehow, against all odds, you want the key piece coming back in the deal to level up into something they’ve never been before. You want the guy you didn’t give up all that much to get to find another gear and become the best player on the team. No, screw that, since we’re getting crazy, maybe the best player in the whole league.

In other words, you want your team’s blockbuster to turn into the Doug Gilmour trade. But the problem with Doug Gilmour trades is that they don’t happen very often. Maybe, you could argue, only once.

We can still feel the impact of the Doug Gilmour trade today. It screwed up the perception of how trades work for an entire generation of hockey fans. It decimated a Stanley Cup winner that still hasn’t won another title since. And it reinvigorated a hockey market that wasn’t quite dying but was certainly in a coma, one self-inflicted by two decades of incompetence.

And yeah, if you haven’t guessed it by now, this is one of those pieces that’s going to get kind of Maple Leafs-centric, even though Gilmour played over two-thirds of his 20-year career for a collection of a half-dozen other teams. If you’re the sort of person who’s bothered by that, I don’t know what to tell you. Doug Gilmour, who comes in at No. 66 on The Athletic’s list of the greatest players of the NHL’s modern era, was a very good player for a very long time for a very long list of NHL teams. But for a couple of seasons in Toronto, he became something more, and that’s what we’re going to focus on because this is my piece.

Let’s look back at the most important trade in the history of the NHL, assuming you define that history through the eyes of a thoroughly disillusioned and hopeless young Maple Leafs fan.

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