With the hockey off-season staying quiet and the Toronto Blue Jays flatlining, the biggest news in Canadian pro sports continues to be the Toronto Raptors‘ recent blockbuster. By adding Kawhi Leonard, the team may have improved their chances of winning the Eastern Conference next year. But the deal came at a cost, with the popular DeMar DeRozan heading to San Antonio in the deal.
That’s a tough spot for an organization, because DeRozan didn’t want to be traded. He made that clear before the trade, and especially so in the days immediately after. Sports is a business, as we’re constantly reminded, but it’s difficult for a fan to see a popular player leave town against his will.
Every now and then, we see something similar in the NHL. Most big hockey deals are pulled off with at least some cooperation from the player, and some are outright forced by a star who wants to be elsewhere. But occasionally, a star is traded against his will. Here are eight times it happened, and how it worked out for everyone involved.
1. Wayne Gretzky, 1988
The player: Wayne Gretzky. You may have heard of him.
We may as well start with the obvious example of a player’s grief at being dealt. Gretzky’s press-conference breakdown, complete with his quip about how he’d “promised Mess I wouldn’t do this,” is burned into the memories of a generation of hockey fans.
The trade: The Oilers — or more specifically, owner Peter Pocklington — sent Gretzky to Los Angeles along with Mike Krushelnyski and Marty McSorley in exchange for Jimmy Carson, Martin Gelinas, three first-round picks and a truckload of cash.
How unhappy was he? That’s a matter of at least some debate; Pocklington would later infamously accuse Gretzky of shedding “crocodile tears” at the press conference. It’s true that by the time the deal was officially made, Gretzky wanted to go to L.A. — according to one version of the story, he was given the chance to back out of the move that morning and chose to go through with it. But all of that came after it had been made clear that Pocklington had been working on a trade for a while, and it’s hard to blame Gretzky for eventually going along with the inevitable.
How’d that work out for them? On the one hand, the trade was a disaster for the Oilers. Carson was good but lasted only one full season in Edmonton, Gelinas was just OK, and none of the three firsts turned into franchise players. Meanwhile, Gretzky won the Hart in his first year in L.A. and added three scoring titles.
On the other hand, the Oilers won the Stanley Cup in 1990, while Gretzky and the Kings never did combine for a championship. So who really won the trade? [Checks notes.] Right, the Kings won by a mile.
We’ll be back in Edmonton a little later in this piece, but for now let’s skip ahead a few decades to a different Canadian team…
2. P.K. Subban, 2016
The player: Subban had won the Norris in 2013 and been a finalist in 2015. But he was also carrying a $9-million cap hit, the highest of any defenceman in the league at the time, and had a no-trade clause that was days away from kicking in.
How unhappy was he? He certainly didn’t want to be moved — that’s why he’d negotiated that NTC. And he’d put down roots in Montreal, including making a $10-million donation to a local children’s hospital. He seemed to take the move personally, and earlier this week, he empathized with DeRozan’s situation.
How’d that work out for them? Habs fans will claim that it’s too soon to tell, and maybe it is. But in the two years since the deal, the Predators have been to a Stanley Cup final and won a Presidents’ Trophy, while the Canadiens haven’t won a round and are coming off a miserable season that has some calling for them to blow it up and start all over. Meanwhile, Subban just posted yet another Norris-calibre season, while Weber missed most of last year and will be out for the first half of this coming season.
We’ll just mark that down as “Advantage: Nashville” so far. But the good news for Montreal is that Weber still has eight years left on his deal, so there’s plenty of time to turn things around.
3. Phil Esposito, 1975
The player: Esposito had been the NHL’s top goal-scorer for six straight years, racking up totals that the league had never seen before (including a then-record 76 goals in 1970–71). He was 33 and had just signed a four-year extension that he figured would keep him in Boston through the rest of the decade.
The trade: In a November deal that caught everyone off guard, the Bruins sent Esposito and Carol Vadnais to the Rangers for Brad Park, Jean Ratelle and minor leaguer Joe Zanussi.
How unhappy was he? At the time, Esposito said he was “crushed” by the move, but added that he had “no regrets towards the Boston management”. That sentiment didn’t last long; over the years, Esposito became increasingly bitter about the trade, and in 2013 he told a reporter that he had no sense of loyalty towards the Bruins, because “I didn’t choose to leave Boston. I signed a contract in Boston for less money than I could have gotten from going to the WHA…. And you know how they repaid me? Three weeks later, they traded me.”
How’d that work out for them? Esposito’s numbers fell off as a Ranger, although he still averaged over 30 goals a season in six years in New York. Ratelle was nearly as productive in Boston, and Park stepped in to help fill the void left by Bobby Orr, finishing as the Norris runner-up twice as a Bruin.
There’s also an epilogue on this deal. Months later, the two teams hooked up on another trade, this one sending Esposito’s old linemate Ken Hodge to New York. That deal brought Rick Middleton to Boston, where he’d spend 12 years and post five straight 40-goal seasons.
4. Mark Recchi, 1992
The player: You might be expecting to see another early-’90s Penguins trade on this list; most fans remember the 1991 deadline blockbuster that sent Ron Francis from Hartford to Pittsburgh. But while Francis may not have wanted to leave the Whalers, he wasn’t exactly brokenhearted to get away from head coach Rick Ley, and he’d known he was on the trade block in the weeks before the deal.
So instead, let’s go with a deal the Pens pulled off a year later, when they sent a 24-year-old Recchi to the Flyers one year after he’d posted a team-high 113 points.
The trade: Pittsburgh sent Recchi, Brian Benning and a first to the Flyers for Rick Tocchet, Kjell Samuelsson, Ken Wregget and a third. The Kings were also involved in the deal.
How unhappy was he? He was “destroyed,” according to teammate Ulf Samuelsson. Recchi had taken less money to re-sign with the Penguins in the off-season, only to be dealt months later. But what’s especially interesting here isn’t just Recchi’s reaction, but those of his former teammates. Kevin Stevens ripped into Penguins’ management over the deal, saying “It’s funny when people say athletes look out for themselves, that all they want is money. It just goes to show you that you’ve got to watch out for yourself.”
Meanwhile, the Penguins already had two veteran backups in Wendell Young and Frank Pietrangelo, both of whom were furious to see Wregget arrive. It was the sort of move that threatened to fracture a championship team.
How’d that work out for them? After everyone was done complaining, the Penguins went out and rolled to a second straight Cup, helped along by Tocchet’s 19 points in 14 playoff games. Maybe they weren’t so fractured after all.
5. Joe Thornton, 2006
The player: A former first-overall pick, Thornton was 26 years old and had a 101-point season under his belt. But he’d never quite met expectations in Boston, and some disappointing playoff runs had some wondering if he ever would. Two months into the 2005–06 season, the struggling Bruins shocked many by pulling the trigger on a deal.
The trade: Thornton went to San Jose for Brad Stuart, Marco Sturm and Wayne Primeau.
How unhappy was he? Thornton told reporters that he was “blindsided” by the deal, and hadn’t wanted to leave Boston. But he didn’t seem all that crushed to be parting ways with GM Mike O’Connell and coach Mike Sullivan.
“Obviously [the Bruins] believe in their coach and their general manager, and I’m next in line, so I’ve got to move on,” he told reporters. “I came back here to win, and we haven’t been winning. Whose fault is that? I’m not sure, but I’m out of here, so it must be mine.”
How’d that work out for them? For Thornton, I’d say pretty well. He lit it up in San Jose, becoming the first NHL player to ever win the Hart Trophy as league MVP in the same season he was traded. He’s been a Shark ever since.
As for the Bruins, on paper they lost the deal badly. But they did eventually win a Stanley Cup, a result that’s eluded Thornton and the Sharks, and to this day some in Boston swear the deal was really a win.
6. Paul Coffey, 1996
The player: Paul Coffey, the first-ballot Hall of Famer who at this point was 35 years old but just one season removed from winning the 1995 Norris Trophy.
The trade: Days into the 1996–97 season, the Red Wings sent Coffey, Keith Primeau and a first-round pick to the Hartford Whalers for Brendan Shanahan and Brian Glynn.
How unhappy was he? Super unhappy, which seems sort of odd given that Coffey was traded roughly three dozen times in his career and probably should have been used to it. But he was so upset at the prospect of becoming a Whaler that he reportedly tried to sabotage the trade after the teams had already agreed to it. According to one version of the story, Coffey called Whalers’ GM Jim Rutherford to try to get him to back out of the deal, and also may have tried to convince Primeau to join him in refusing to report. It didn’t work, but you kind of have to admire the commitment.
How’d that work out for them? The acquisition of Shanahan is often seen as the move that turned the Red Wings from regular-season warriors into Stanley Cup champions. As for Coffey, he eventually reported to Hartford but lasted just 20 games before they sent him to Philadelphia. The Whalers didn’t last much longer; they were in Carolina within a year.
7. Ryan Smyth, 2007
The player: By 2007, Smyth was the Oilers’ most popular player, not to mention a borderline national hero due to his regular appearances with the national team at the World Championships. He’d helped the Oilers get to the Cup final a season before, but with the team sputtering he went into the 2007 deadline needing a new contract.
The trade: In a jaw-dropping move that seemed to come out of nowhere, the Oilers traded Smyth to the Islanders for Robert Nilsson, Ryan O’Marra and a first.
How unhappy was he? Pretty devastated. While he’d apparently known that he could be dealt if an extension couldn’t be reached, Smyth still took the news hard, struggling to get through a farewell press conference. He’d later describe the day as “tough” and “very emotional.”
How’d that work out for them? Is it possible for everyone to lose a trade? Smyth played well enough to help the Islanders make the playoffs, but they made a quick exit and he jumped to the Avalanche as a free agent. Meanwhile, the package the Oilers got back didn’t amount to much.
The trade remains one of the most divisive in recent in history, especially after rumours surfaced that Smyth and the Oilers had been within a few dollars of a new deal. (Smyth later denied that.) But time heals most wounds, and Smyth made his inevitable return to Edmonton in 2011, finishing his career with three seasons there before retiring as an Oiler.
And speaking of beloved stars making their return… [takes deep breath]… let’s do this.
8. Wendel Clark, 1994
The player: By the end of the 1993-94 season, Clark was the Maple Leafs’ captain and had firmly established himself as the most popular Toronto player of his generation. He was coming off a career-high 46 goals (in only 64 games) and had just posted two of the top five post-seasons ever by a Maple Leaf in terms of goals scored, not to mention the hat trick in L.A. and his righteous obliteration of Marty McSorley for the crime of being mean to Doug Gilmour. He pretty much walked on water in Toronto.
In the eyes of the fans, that made him untouchable. In the eyes of Cliff Fletcher, that made him a 27-year-old asset that would never carry more trade value.
The trade: In a draft-floor blockbuster that drew an audible gasp from the Hartford crowd when it was announced, the Leafs sent Clark, Sylvain Lefebvre and Landon Wilson to the Nordiques for Mats Sundin, Garth Butcher and Todd Wariner. The two teams also swapped first-round picks.
How unhappy was he? The normally stoic Clark shed tears as he spoke to the media after the trade was announced. He’d had no idea the deal was coming, and had figured he would spend his entire career as a Maple Leaf. Most fans did, too, with thousands showing up for a sendoff at Mel Lastman Square, and it’s fair to say that the initial reaction in Toronto was best summed up by Don Cherry.
How’d that work out for them? Well… I mean…
[Glances at #17 Leafs tattoo.]
I guess it was…
[Watches the “All Heart” video on loop for three hours.]
I mean you could make the case that…
[Thinks about his two beloved children, Wendel and Other Wendel.]
Look, it was a good trade, OK? Fletcher did the right thing when he traded Wendel Clark.
From the outside, that’s blindingly obvious — the Nordiques got only one season from Clark, while the Leafs got 13 years of Mats Sundin’s first-ballot Hall of Fame career. If we’re being honest, this was probably one of the more lopsided trades of the ’90s.
But to a Leafs fan, even knowing how well Sundin’s tenure went, the Clark trade is still a tough one to look back on. It helps somewhat that he was back in Toronto by 1996, and even made a second return in time for the 2000 playoffs.
That may be the best-case scenario for Raptors fans still wondering about the DeRozan deal – not so much the homecoming, but the grudging acceptance that the deal really was for the best. It took some Leafs fans the better part of 13 seasons to get there. Time will tell whether Raptor fans get more than one to feel the same way about Leonard.