Monday marks the 25th anniversary of one of the biggest trades in NHL history: the blockbuster 1992 deal that sent Doug Gilmour from the Calgary Flames to the Toronto Maple Leafs.

In hindsight, it was the trade that reinvigorated a Maple Leafs franchise still digging out from the Harold Ballard era, while extinguishing any hope that the Flames’ Stanley Cup contender status could be revived.

Hearing the move announced for the first time back then was a legitimately stunning experience; once the names started, they just kept coming. The deal involved 10 players, sending Gary Leeman, Michel Petit, Jeff Reese, Craig Berube and Alexander Godynyuk to the Flames in exchange for Gilmour, Jamie Macoun, Ric Nattress, Rick Wamsley and Kent Manderville.

In terms of the sheer number of players involved, the deal really was the biggest in NHL history, and remains so to this day. And while other trades may have had a bigger impact – Wayne Gretzky, Eric Lindros and Phil Esposito all come to mind – that list is a relatively short one.

So today, let’s celebrate the deal’s silver anniversary with 25 facts about the Doug Gilmour trade.

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1. The trade happened the day after Gilmour walked out on the Flames.

Let’s lead off with this one, because it’s important but has somehow been largely forgotten over the years.

These days, the trade is held up as a classic lopsided blockbuster, and as we’ll get to, that’s a fair assessment.

But it’s not like the Flames just woke up one day and said “Let’s trade a really good player for a bunch of worse ones.” They kind of had no choice.

Gilmour was miserable in Calgary, feuding with GM Doug Risebrough (and at one point, allegedly overhearing a phone call in which Risebrough talked about trading him). Mix in a contract dispute that was turning fans against him, and it was well-known that Gilmour wanted out.

But things escalated on New Year’s Day. Hours after putting up two points in a win over Montreal, Gilmour packed up his gear and left the Flames. The deal had obviously been in the works long before that – 10 player deals don’t just come together in 24 hours – but Gilmour’s walkout sped things along and stripped the Flames of virtually any remaining leverage.

It gets in the way of the “dumb team gives away a superstar” storyline, but fair is fair. You can’t tell the story of this trade without mentioning that Gilmour was already an ex-Flame when it happened.

2. Risebrough knew the Flames pretty well

Most fans know that Risebrough was the Flames GM at the time. What isn’t as well remembered is that he was also in his second season as the team’s head coach.

Pulling double duty was relatively rare back then, though not unheard of, and in theory Risebrough would have had a chance to evaluate the players he was trading away up close.

(As a side note, his dual status didn’t last long. Two months after the Gilmour trade went down, the Flames lost to the Canucks 11-0 and Risebrough resigned as coach. He’d remain as GM until 1995, though.)

3. Cliff Fletcher knew the Flames pretty well, too

Fletcher had been the first and only GM in Flames’ franchise history until after the 1990-91 season, when he headed to Toronto to assume near total control of the Maple Leafs. This wasn’t his first Leafs blockbuster – that would have been the September 1991 deal that saw Toronto acquire Grant Fuhr and Glenn Anderson from the Oilers. But it was his first chance to deal with his old club, and with the man who had replaced him.

Needless to say, Fletcher knew the players he was getting at least as well as the ones he was giving up. And in hindsight, it showed.

4. A Gilmour/Leeman trade had been rumoured for weeks

Even before Gilmour forced the Flames’ hand, rumours had been flying that a deal would send him to Toronto for Leeman. The Leafs’ winger was having an awful season, with just seven goals through the first half, but was still less than two years removed from scoring 112 goals over three seasons, peaking with 50 in 1989-90.

Things had fallen apart for Leeman in November 1990, when in the span of 24 hours the Leafs traded away his centreman, Ed Olczyk, and he suffered a serious shoulder injury.

He was still feeling some lingering effects of that injury and hadn’t clicked with new linemates; the idea that he could get healthy and regain his scoring touch next to someone like Joe Nieuwendyk or Theo Fleury wasn’t all that far-fetched.

But even given that, most figured that a straight up one-for-one deal probably didn’t make sense, and that a player or two would have to be thrown in to make it work. We just didn’t realize that “a player or two” would end up ballooning to eight other names.

5. One of the worst losses in Leafs history may have helped the deal go down

While Gilmour’s walkout was the biggest factor in pushing the Flames towards a deal, the Maple Leafs may have been given a nudge of their own by one of the worst performances in franchise history. On December 26, 1991, the Leafs went to Pittsburgh and got blown out by a score of 12-1.

Any thoughts of patience on Fletcher’s part probably evaporated as he watched the defending champs toy with his sad-sack team. Chance was going to be needed, and minor tinkering wouldn’t cut it. One week later, he pulled the trigger on the trade that blew his roster to smithereens.

6. The deal was a massive ripoff

OK, we’ve defended the Flames as much as possible. But even given Gilmour’s walkout and Fletcher’s inside info, this deal was awful. Even Risebrough later admitted that, calling the move “a mistake by a very young general manager.” The trade was so bad from Calgary’s perspective that even if you remove Gilmour from the equation, they still barely break even.

And by the way, this isn’t just 20/20 hindsight talking. Even at the time the trade was made, the general consensus was that the Leafs had made out like bandits. Calgary papers referred to the deal as a robbery and ran editorial cartoons of Fletcher making off with a haul while Risebrough was left wearing a barrel. And Toronto media could barely contain their glee.

7. If there was one concern in Toronto, it was age

The 1991-92 Maple Leafs weren’t just bad. They were also old—or at least older than you’d like a last-place team to be.

Their leading scorer was 31-year-old Glenn Anderson, and the roster was dotted with guys like Mike Foligno, Mike Krushelnyski and Lucien DeBlois. The team’s best young players were guys like Daniel Marois and Rob Pearson, and the prospect pipeline wasn’t especially well-stocked.

So there was some concern in Toronto when the team pulled off a trade centered around a star player in Gilmour who was already 28, two defencemen who’d be 30 by the end of the season, and a 32-year-old goaltender.

Manderville was the youngest player in the trade, but Godynyuk was only 22 and all the players the Leafs gave up were 27 or younger.

In the end, it didn’t really matter. But Fletcher’s willingness to get older for the sake of short-term improvement – just like he’d done in Calgary – may have foreshadowed Toronto’s “draft schmaft” future.

8. None of the players the Flames received lasted long in Calgary

If the idea behind the move was to reshape the Flames for the long-term, it didn’t quite work out. By the end of the 1993-94 campaign, all five players who came over in the deal had departed the Calgary roster.

That included Petit leaving as a free agent and Godynyuk being claimed in the 1993 expansion draft, as well as three trades. In case you’re wondering if any of those trades ended up redeeming the initial mistake… well, not so much. The Flames’ total haul from those deals: Dan Keczmer, Brian Skrudland and a fifth-round pick.

9. Jeff Reese stuck around long enough to set an NHL record

While Reese didn’t last long in Calgary, appearing in just 39 games, he did manage to set an NHL record that still stands to this day, and probably will for a long time.

On Feb. 10, 1993, Reese was in net as the Flames hosted the Sharks. He gave up the opening goal just three minutes in, but from then on it was all Calgary as they pumped home 13 goals in one of the biggest blowouts in league history.

Theo Fleury was a ridiculous plus-9 in the game, and Reese became the first and only goalie to have three assists in a single game.

10. The deal helped Michel Petit set a record too, although it took a bit longer

It’s fair to say that Petit got around. The Leafs and Flames were his fourth and fifth stops in the NHL, and it turns out he was only halfway done. He’d end up playing for 10 different teams, and he recorded a point with all of them, making him the first player in league history to get on the scoreboard for 10 franchises.

11. The deal capped off a busy year for Craig Berube

The notorious tough guy (and future Flyers coach) had come over to Toronto from Edmonton in the Fuhr deal in September. He’d never even suited up for the Oilers, having arrived there in an off-season trade with Philadelphia.

That Flyers trade was a six-player deal centered around Jari Kurri and Scott Mellanby. Factor in the seven-player Fuhr trade and the 10-player Gilmour deal, and in just over seven months Berube was involved in three trades totaling 23 players (including four future Hall-of-Famers).

Given today’s conservative trading landscape, it’s safe to say that’s a record that will never be broken.

12. Leeman got off to a truly terrible start in Calgary

Any hopes of Leeman regaining his scoring prowess in Calgary vanished fairly quickly. He made his Flames debut in a home-and-home series against the Oilers, and was held pointless.

That was just the beginning.

It took Leeman a remarkable 20 games to score his first goal as a Flame, and he wouldn’t manage a single multi-point game over the rest of the season. He finished the year with just two goals and seven assists in 29 games.

He was somewhat better in 1992-93, scoring nine times through 30 games, but by that point it was too late. Just over a year after the Gilmour trade, the Flames sent Leeman to Montreal in a straight-up deal for Skrudland.

13. In one sense, Leeman still got the last laugh

Only two of the 10 players in the deal went on to win a Stanley Cup afterwards. One of those was Leeman, who earned his ring with the Canadiens in 1993. He suited up for 11 games during that playoff run, scoring once.

14. Gilmour made an impact early on – literally

While he didn’t blossom into one of the league’s top offensive threats until the following season, Gilmour scored at a better than point-a-game pace with Toronto, including multi-point outings in his first and third game as a Leaf.

But while he’d make his mark for his play-making, goal-scoring and two-way play, Gilmour’s first true highlight as a Maple Leaf may have come in his sixth game with the team, when he found himself staring down a crazed Stu Grimson during a wild brawl in Chicago.

While every Leaf fan probably saw their new franchise player’s life flashing before their eyes, Gilmour showed off some unexpected grappling skills by taking Grimson to suplex city.

(He wouldn’t’ debut what would become his patented finisher, the head butt, until a year later.)

15. Gilmour wasn’t the first player to wear #93 for the Maple Leafs

Gilmour wore No. 39 in Calgary, but chose to flip that into what would become his iconic No. 93 in Toronto. This was during an era where high numbers were typically reserved for superstars like Wayne Gretzky, so the choice was a bit of a daring one.

But Gilmour’s play lived up to the hype, and to this day you can still find blue-and-white No. 93 sweaters dotting the crowd at pretty much any Maple Leafs game. The number is so closely associated with Gilmour that Mitch Marner wouldn’t take it when it was offered to him earlier this year.

All of which makes it a little bit odd that Gilmour wasn’t the first player to wear the number in Toronto. He wasn’t even the only one to do it in this trade.

Instead, that honour belonged to Godynyuk, who became the first player in NHL history to wear No. 93 when he debuted in Toronto during the 1990-91 season. One version of the story says Godynyuk chose the number because he was the third Soviet defector of the 90s, following Sergei Fedorov and Alexander Mogilny.

16. The trade didn’t include any picks, and only one prospect

It’s one thing to pull off a deal involving 10 players. But unlike just about every other high-volume trade in modern history, this one was made up almost entirely of established NHLers. The deal didn’t include any draft picks, and only one prospect.

That prospect was Kent Manderville, a 20-year-old forward who was spending the season with the Canadian national team. He was already committed to playing in the 1992 Winter Olympics, where he’d have three points in eight games to help Team Canada to a silver medal.

Manderville debuted for the Maple Leafs later in the season, and went on to bounce around the league during a decade-long career as a low-scoring checking forward. He had some decent moments in Toronto, but Leafs fans may best remember him as the guy who whiffed on a check against Wayne Gretzky in Game 7 of the 1993 conference final.

17. The deal’s biggest loser may have been Rick Wamsley

The Flames’ veteran backup had been looking for a trade for months. Stuck behind established starter Mike Vernon in Calgary, Wamsley was concerned that his lack of playing time would prevent him from landing another contract in the league. So he’d asked the Flames to move him to a team where he’d have a chance to play more.

Instead, he was sent to the Leafs, who already had a future Hall-of-Famer in net in Fuhr, not to mention prospect Felix Potvin on the way.

Wamsley would make only eight appearances for the Maple Leafs the rest of the season, and just three the following year. He never did get that contract, and was out of the league by 1993.

18. Ric Nattress’s stint in Toronto ended quickly and controversially

Nattress was a veteran defenceman who was hurt at the time of the deal. He appeared in 38 games for Toronto that season, scoring 16 points (including beating Patrick Roy from centre ice on Hockey Night in Canada for his first goal as a Leaf).

But at the end of the season, Nattress’s contract status ended up being in question. The CBA dictated that any 10-year veteran making less than the league average salary was eligible for unrestricted free agency, but didn’t actually define what “league average” meant. The case ended up going to a neutral arbitrator, who sided with Nattress and declared him a free agent. Nattress signed with the Flyers shortly after.

19. Jamie Macoun lasted longer with his new team than anyone else in the deal

Given how quickly most of the players in the trade ended up in new homes or out of the league altogether, you might assume that Gilmour stuck around longest.

Instead, that honour belongs to Macoun, who played nearly seven seasons in Toronto, outlasting Gilmour by one year.

An additional fun fact: despite being a defensive defenceman, Macoun’s 101 points with the Leafs was more than all five players on the Flames side of the deal managed in Calgary, combined.

Macoun finally punched a ticket out of Toronto at the 1998 trade deadline, heading to Detroit for a fourth-round pick. That deal, small as it was, worked out well for both teams. The Leafs turned the pick into Alexei Ponikarovsky, and the Red Wings went on to win their second straight championship that spring, allowing Macoun to join Leeman as the second member of the 1991 blockbuster to pick up a post-trade Cup ring.

20. Heading to Toronto greatly increased Gilmour’s marketability, with mixed results

By the time he’d put up 127 points in his first full season with the Leafs, Gilmour was one of the biggest stars in hockey, and playing in a major media market led to plenty of chances to pick up sponsorship deals.

Sometimes, that meant having cool hair.

Other times, it meant, well, this:

The 90s were weird.

21. The Flames and Leafs hooked up for another trade a few days later, but it was slightly smaller

Apparently feeling that swapping 10 players just wasn’t quite enough, Fletcher and Risebrough threw one more name into the mix less than two weeks later.

On Jan. 15, 1992, the two teams completed a trade that didn’t quite generate the same headlines: The Flames sending minor leaguer Todd Gillingham to the Leafs for cash.

Gillingham never did play in the NHL, but he was traded three times, each of which involved him shuffling back and forth between the Flames and Leafs.

22. Flames fans still aren’t quite over all of this

Don’t worry, we can talk about them. Every Calgary fan punched a hole in their screen the second they saw the headline on this post.

But yeah, it’s fair to say that Flames fans haven’t exactly gone with the whole “forgive and forget” thing.

They’re still mad. Just a bit cranky. A little ornery. Mildly irritable.

Can you blame them? No, you cannot.

23. Over a decade later, the Leafs traded for Gilmour a second time. It didn’t end well.

As memorable as it was, Gilmour’s stint in Toronto only lasted a little more than five years, as he was traded to the Devils in advance of the 1997 deadline. He’d go on to bounce around four teams in six seasons, including a stint with Montreal.

That’s where he was at the 2003 deadline, when the Habs agreed to send him back to Toronto for a sixth-round pick. It was a classic rental move; the Leafs were quasi-contenders, and bringing back Gilmour as a depth guy seemed like the sort of inspirational move that could spark the team to a playoff run. At the very least, they’d get a great moment when Gilmour first stepped onto the ice in Toronto wearing the blue and white.

It never happened. Instead, Gilmour made his Leafs return on the road, was involved in an awkward collision, and suffered a career-ending knee injury.

His Toronto comeback lasted just five shifts.

The location of that lone comeback game? Where else but Calgary.

24. The Fletcher family wasn’t done with Risebrough quite yet

Cliff Fletcher remained with the Maple Leafs until 1997, and with the exception of a brief stint with the Coyotes and an interim role with the Leafs, that was the end of his career as an NHL GM.

That probably came as a relief to Risebrough, who moved on to a role in the Oilers’ front office in 1996 before being named the first GM of the expansion Minnesota Wild in 1999. Building a team from the ground up is always a tough job, but at least Risebrough would be able to do it without being haunted by Fletcher, and memories of the ambitious blockbuster that backfired so badly.

Well, that ends up being mostly true. But in 2009, after nearly a decade on the job in Minnesota, Risebrough was relieved of his duties. His replacement: Chuck Fletcher.

Yes, the son of the man who fleeced him on the Doug Gilmour deal.

25: If you remember the day this deal went down, this post made your feel really old

Sorry about that. Feel free to yell at some clouds if it makes you feel better.