Welcome to NHL99, The Athletic’s countdown of the best 100 players in modern NHL history. We’re ranking 100 players but calling it 99 because we all know who’s No. 1 — it’s the 99 spots behind No. 99 we have to figure out. Every Monday through Saturday until February we’ll unveil new members of the list.
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.
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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.
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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.
We’ll start our story in the mid-1980s, as Doug Gilmour and the Toronto Maple Leafs franchise lurch toward an eventual meeting that will redefine both of them.
Gilmour came into the league as a long shot to have any impact at all. He was drafted in the seventh round by the Blues in 1982, an undersized center in an era when that was often enough to get scouts to look the other way. He scored an impressive 119 points in the OHL in his draft year, then exploded for 177 points after being sent back for the 1982-83 campaign. That put him on the NHL radar, and he made the Blues in 1983-84, playing a full season and producing a respectable 53 points. From there, he took strides in each subsequent year, helping the Blues to a playoff run in 1986 and then peaking in 1986-87 with a season that saw him crack the 40-goal and 100-point marks for the first time, finishing fifth in Hart Trophy voting and sixth for the Selke.
The offensive numbers weren’t especially noteworthy in the run-and-gun ’80s, but the two-way game was; this was back in the day before players like Sergei Fedorov, Pavel Datsyuk and Patrice Bergeron redefined the position. Back then, you had your scorers and you had your checkers, and it was rare to find a center who could fill both roles. Gilmour could, and it made him one of those players that smart fans knew was more valuable than his stat line suggested. Not a superstar, not quite, but an underrated gem.
Gilmour was traded to the Flames in 1988 under circumstances that were well covered at the time but seem largely forgotten today. The trade was a steal for Calgary, helping them return to the Final in 1989, where Gilmour scored the Stanley Cup-winning goal. He spent three full seasons as a Flame, settling in as a guy who could be counted on for 80 to 90 points and strong defensive work. Surrounded by stars on a Flames team that aspired to another championship, Gilmour was a key piece of the puzzle. Again, not quite a superstar, but the sort of player you want on the ice in a big game.
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Meanwhile, the Maple Leafs were terrible. That’s really all you need to know. If you’re a “why” sort of person, then you can read all about Harold Ballard, the worst owner in the history of the league, and how he ran a once-proud champion into the ground. Or you can just take my word for it: By the early 1990s, the Maple Leafs were a joke, if you were young enough then they had always been a joke, and if you were paying attention then they would always be a joke, and that was all you ever needed to know about the team.
What nobody could have suspected was that it was all about to change.
The key name you need to know is Cliff Fletcher. He had run the Flames for nearly 20 years, stretching back to their Atlanta days, and he’d built that 1989 Cup winner. He’d been the guy who brought Gilmour to Calgary. And now he was in Toronto, having become the Leafs general manager in 1991, a year after Ballard’s death. He was a throwback GM, the kind who’d be almost unrecognizable to today’s fans, which is to say that he actually did things. When his team was bad, Fletcher didn’t mumble about patience and five-year plans and playing it safe. And that was good news for those Maple Leafs because they were indeed very bad.
Fletcher took over a team that had just finished 20th in a 21-team league and had no first-round pick because they’d traded it away years ago for Tom Kurvers, and I’m still not ready to talk about that one. He got to work almost immediately, acquiring Grant Fuhr and Glenn Anderson from the Oilers in a blockbuster trade. For many GMs, that would have become his signature move. For Fletcher, it was a warmup.
In Calgary, Fletcher’s replacement was Doug Risebrough, a young hockey mind who was serving double duty as coach and GM. His team was off to a rough start, playing barely .500 hockey through the season’s first few months. As Christmas approached, the Flames were no sure thing to make the playoffs in a tough Smythe Division.
Risebrough knew that a change was needed. And so, when his old boss Fletcher called, Risebrough picked up the phone and the two got to work on a trade that would soon grow to become the largest in NHL history. The Leafs would get Gilmour and the Flames would get Gary Leeman, a winger who had scored 50 goals in 1990-91. Names were added on both sides, with the Leafs adding veterans like Jamie Macoun and Ric Nattress while the Flames got younger pieces like Jeff Reese and Alexander Godynyuk. By the time they were done, there were five players on each side of the deal. It was a blockbuster.
Rick Wamsley, left, and Doug Gilmour arrive at Pearson Airport after being traded to Toronto. (Ron Bull / Toronto Star via Getty Images)
It was a ripoff. We’ll get back to Gilmour in a minute, but even if you take him out of the deal, the Leafs still won it. Leeman had already been slumping and was a bust in Calgary, scoring just two goals that year and 11 in total before being sent to Montreal for checking center Brian Skrudland. Nobody else that the Flames got had much impact. Macoun was the second-best player in the deal. It was, to put it bluntly, a disaster for the Flames. And as that became apparent, a narrative quickly formed: The old master had taken advantage of his apprentice. Fletcher knew the Flames better than Risebrough did, and he’d robbed him blind. The Flames had been played for chumps.
Oh, and also, Gilmour had walked out on the Flames in the days leading up to the deal.
That part gets skipped over these days, and it admittedly dulls some of the drama here, but it’s true. Gilmour wanted out, partially due to a feud with Risebrough and partly because of a contract dispute, and he’d gone home to force the Flames’ hand. That’s not the only reason the trade happened — it had already been in the works for weeks — but it ended any leverage that Flames had.
The deal was done on a day some Toronto fans still know by heart: Jan. 2, 1992. Doug Gilmour was a Maple Leaf.
Gilmour was fine in that first half-season in Toronto. Very good, even. His 49 points in 40 games weren’t eye-popping for the era, but they were good enough to make Gilmour the Leafs’ best player. He even took Stu Grimson to suplex city, which was cool.
Then, at some point between the end of that 1991-92 season and the start of 1992-93, something happened. We’re still not quite sure what, although the hiring of Pat Burns as coach was probably a big part of it. But whatever it was, Gilmour went supernova. For the next two years, he may have been the best player in the NHL. OK, fine, the best player who wasn’t Mario Lemieux, but if we’re limiting this to mere human beings, then Gilmour tops the list.
In his first full season with the Maple Leafs, Gilmour shattered the franchise record for points with 127, while winning the Selke and finishing second in Hart voting to Lemieux. He was somehow even better in the playoffs, scoring an iconic goal and leading the Leafs to the conference finals while racking up 35 points. To this day, that ranks in the top 10 for the most productive postseasons ever — on a team that didn’t even make the Final. It was one of the most amazing playoff performances anyone had ever seen, unless you’re Kerry Fraser, in which case you weren’t watching.
Gilmour was nearly as good in 1993-94, posting 111 points while finishing second in Selke voting and fourth for the Hart. Dave Andreychuk, acquired in yet another Fletcher blockbuster, clicked with him instantly and had back-to-back 50-goal seasons on his wing. The Leafs made another conference finals.
And along the way, Gilmour took over Toronto. He wasn’t just the city’s most popular athlete, which was no small feat given the Blue Jays were winning World Series. He was also its coolest, a genuine celebrity who embraced the role in a way few hockey players do. For those years, every road hockey game in Toronto was divided between kids who wanted to be Doug Gilmour and kids who still wanted to be Wendel Clark, and Gilmour may have had the edge. The hair was cool. The leather jacket was cool. The casual goal celebrations were cool. The motorcycle was cool. The loose chin strap was cool. The cow legs were … look, we were even willing to overlook the cow legs. That should tell you all you need to know.
This video, produced by the Maple Leafs as part of a campaign to get him that 1993 Hart Trophy, might be the most early-’90s thing on YouTube. I mean that as a compliment.
Gilmour’s ascent to the very top of hockey’s stardom tier was a good thing that involved the Maple Leafs, so it goes without saying that it couldn’t last. The Leafs overhauled the roster during the 1994 offseason, making the Clark-for-Mats Sundin trade and other moves, and when the lockout ended in time for a shortened season, the vibe wasn’t the same. Gilmour was still very good at both ends of the ice, but his production dropped and the team stopped winning playoff rounds. Burns was fired, Andreychuk was traded and it soon became apparent that a looming rebuild meant that Gilmour would go too.
That day came midway through the 1996-97 season, with the Leafs dealing Gilmour to the Devils for a package of young players. It kicked off a period of Gilmour’s career when he became a hockey nomad, mostly playing well in stops in New Jersey, Chicago, Buffalo and Montreal, where he proved he still had the cool factor when he managed to do this without flinching. He returned to Toronto at the 2003 deadline, in what was set up to be one final run for the Cup in front of the fans that had loved him best. Instead, he blew out his knee in his first game back, and never played again.
All told, Gilmour’s career spanned 20 seasons and saw him rack up 1,414 points, good for 21st spot on the all-time list, and he was inducted into the Hockey Hall of Fame in 2011. Of those 20 seasons, only three were full ones in Toronto. But as good as he was in St. Louis and Calgary, and as many moments as he had elsewhere, he’ll always be a Maple Leaf.
And he’ll always be the guy you’re thinking of when your team makes a trade. Will that scrappy top-six forward you’re bringing in suddenly blossom into one of the very best players of his era, if only for a couple of years? It could happen. It happened once before. It probably won’t happen again, but have some cow legs ready, just in case.
(Top photo: Jamie Squire / Getty Images)