On July 18th, 2018, a basketball trade was made that would change Toronto sports forever. In what felt like an absolute shocker to the entire city, fanbase, and frankly the whole sport at the time, Masai Ujuri pulled the trigger on a deal that sent DeMar DeRozan, Jakob Poetl and a first-round draft pick to the San Antonio Spurs in exchange for Kawhi Leonard and Danny Green.
Many were shocked to see DeRozan, at the time the most beloved player in the history of the Toronto Raptors, moved at all, let alone for a player correctly expected to be a one-year rental, coming off long-term injury absences and with doubt if he had interest in even coming to Canada at all. In the end, though, it paid off. Kawhi played, he was by and large healthy throughout the year with the help of careful "load management", and he looked like the all-world talent he was believed to be. By the end of the year, he would lead the Raptors to their first NBA Championship, before making his long-expected move home to Los Angeles.
Needless to say, that's the sort of result that makes it all worth it. Kawhi being a one-and-done was a bit of a bummer, and while fans felt bad that DeMar wasn't part of the group that got there, he remains beloved in Toronto and his time here looked upon fondly.
You might be wondering what this has to do with hockey, though. You see, the Raptors share Scotiabank Arena with a few other people, most notably the National Hockey League's Toronto Maple Leafs. The Leafs have built up a fantastic team in recent years, but like the Raptors heading into 2018/19, they've failed to turn it into the playoff success they've hoped to achieve. If anything, their failures have been even more overt - the Raptors won a couple rounds here and there, and were only really stopped by LeBron James. The Leafs, on the other hand, have lost their opening playoff series in six consecutive seasons.
This year felt a fair bit different, with the blue and white not collapsing or playing beneath their potential, but simply losing a close series to the back-to-back defending champion Tampa Bay Lightning. But it's still a loss, and people still want solutions, and there is no easier line to draw to a championship in this city than the Kawhi trade. Elliotte Friedman of Sportsnet made the most-amplified reference to the trade in his interview rounds this week, including making it an anchor point of one of his 32 Thoughts podcast episodes, but it's a reference that's been made throughout Toronto hockey media and fan discourse over the past week, and really, in times beyond. There were even references to it before Kawhi officially confirmed he wasn't staying with the Raptors, when the Maple Leafs traded Nazem Kadri to the Colorado Avalanche nine days before for Tyson Barrie (a high-reputation pending UFA) and Alex Kerfoot (an accessory player in the vein of Green). Of course, that didn't work out as hoped, so we're back on the same topic.
Personally, I'm in disagreement with the whole concept. I think it misunderstands a lot of fundamental issues about the team, the sport, and even the original trade they're referencing.
A Different Situation
The very first thing to address when talking about a scenario like this is what the very foundation of the example case is. The Kawhi trade is melted down to "traded beloved good player for other good player, and the team won", but there are a few situational reasons why you won't be able to draw up a comparable situation.
The most important one is the concept of who has the leverage in the negotiation. If you want to win a trade for an impact player, there are really only two ways to get there - you have to find value that no one knows about, or you have to strongarm the negotiation of a deal. The implication of a Kawhi trade means that we're not looking at the former, as the star would be established in the way that Leonard was. Instead, you need to be the party with leverage in the negotiation.
You know how you don't gain that leverage? By having your player on the market. The Kawhi trade worked because Leonard was known to be on the market, and DeRozan was not thought to be on the market. Go back and look for articles in the months leading into the deal, and the first thing you'll notice is that there was plenty of discussion of where Kawhi would end up, and very little mentioning Toronto as a candidate. There was also no expectation that moving DeRozan would be part of Toronto's plans to move forward - to the point where when he was moved, DeRozan felt extremely wronged by the Raptors organization due to how blindsiding the move was.
Simply put, the trade worked because Kawhi was being sold at less than his value if he was healthy and had term, and DeRozan was put up as a tough concession - both to the salary cap constraints the Raptors had, and to the lack of interest in moving core young players. DeRozan was a good player, but you don't get a Top 5 player for a Top 30 player without something closing the bridge in value.
You know what doesn't close the bridge in value? Having the entire hockey world expect that you want to make a deal, that one of your biggest salary players have to move to make it work, and having to chase around a market that doesn't really have a name on it right now. Seriously, go look at the market, and ask yourself which players in the top-end of league circles might be in trade rumours. We haven't heard much about playoff teams wanting to pull the parachute on their builds, and the list of 70+ point scorers on non-playoff teams is pretty short: JT Miller, Kyle Connor, Patrick Kane, Alex DeBrincat, Timo Meier, and Mark Schiefele. Flip to starting goaltenders who had above-average years, and it's Ilya Sorokin, Anton Forsberg, Thatcher Demko, James Reimer, and Connor Hellebuyck.
Basically, it's a list of young players who their rebuilding teams will want to keep, players on the wrong side of 30, a handful of players who had abnormally good years for their development curves, and the core of the Jets, who came close to making the playoffs this year. There isn't really a Kawhi-type talent in that list of players. To get mega-star talent, you'd have to approach a player and team that is comfortable, and convince them that what you're rumoured to be selling is a worthwhile price. That sort of leverage is insanely unlikely, which would leave you in a position to make a move that you know is a value-downgrade from the second you make it - change for the sake of change, if you will.
Can This Even Work In Hockey?
Another issue in going for something like this is that even if you were to pull the trigger on an impactful premium-for-premium deal, it's extremely unlikely to make the same sort of difference as it did for the Raptors in the NBA.
This is because of a fundamental difference in how rosters are built and deployed in basketball. Top players play a significant share of the game - 2019 Leonard in this example played 34 minutes per game in the regular season and 39 minutes per game in the playoffs, meaning about 70-80% of the available 48 minutes in a regulation game. Teams typically put about eight players on the floor in a given game, with four or five carrying the majority of the workload. In hockey, you have eighteen skaters and two goalies dressed for a given game, and outside of the goalie, playing a majority of available minutes is an incredibly rare occurrence.
The best players in the world still look at about 22 minutes as forwards, and 25 minutes as defencemen, and those numbers are declining over time as the bottom of lineups get more capable and teams focus more on maximizing energy and health. Even Connor McDavid, the sport's best player of this generation and arguably it's most purely capable skater ever, averages about 23 minutes, or 38% of the game. That's about half the relative time of a basketball star to make a difference.
Stathead is a network of websites that track top-level professional sports statistics, most famously in baseball but also in hockey and basketball. They have metrics called Win Shares (NBA) and Point Shares (NHL, which has standings points for overtime/shootout losses) to estimate the value that individual players have on their team's records. In Leonard's season with Toronto, he put up 9.5 win shares in 60 games while "coasting" in the regular season, and 4.9 win shares in 24 games in his legendary, full-effort playoffs that we're trying to replicate here. In McDavid's best regular season, he posted 13 point shares in 56 games, a rate in line with Wayne Gretzky and Mario Lemieux's peaks. Even if we straight up cut point shares in half to create win shares, which might be generous given OT losses, that puts McDavid at 6.5 wins per 56 games at his zenith. In a 24-game stretch like Leonard's playoffs, that would be 2.8 wins, or about 57% of what Kawhi gave to the Raptors.
Again, that's the best skater in the current era of hockey at his peak, making a case to be considered one of the top 1 to 5 all time, and he can't touch what was brought in by that trade. Heck, with DeRozan's single-playoff high being about 1.2 win shares per 24, it's not even touching the difference in the upgrade between the two players.
A better argument can be made if you were to get an all-world goaltender - Roberto Luongo's all-time record 20.9 goalie point shares in 2003/04 would be worth about 3.5 wins in 24 games by the same measurement and it fleshes with the idea that goaltenders' performances can make the biggest swings in a small sample like a playoff game or series, but it still doesn't touch the value of a megastar basketball player, and goalies that can be trusted to be consistently good, let alone all-time great are a rarely-moved commodity in this league.
Do The Leafs Need A Shakeup, Anyway?
To get this sort of impact, it would need to be a trade where you pull in multiple impact players without spending many the other way. An avenue using the names above, for example, would be pulling in Mark Scheifele and Connor Hellebucyk from Winnipeg, and sending John Tavares the other way. A Scheifele-Hellebucyk duo would've been worth about two standings points in 82 games over Tavares and Jack Campbell - not nothing, but not transformative in the way that would keep up with what we're looking for here. You also have to deal with the fact that while there is more speculation about those two Winnipeg players than most of the players we mentioned earlier, the pressure isn't on the Jets in the same way as it is with the Leafs, and neither has the reputation for a heavy contract in the way that Tavares does. Tavares is also the oldest player in this conversation. This would presumably give the Jets a lot of leverage, to the point where Tavares' asset value likely doesn't cover either player, let alone both, even with his production.
Without going into the finer nuances of the trade, we're already stuck on there not being massive surplus value on the roster, the need to spend way more in out-of-roster assets to balance out the trade value, and having very little leverage. And this is the best case scenario, zeroing in on the players most likely to fit the bill based on what we know about the market right now. Following that, the potential gains get lower and lower - a popular proposal for example is moving William Nylander for Washington power forward / wrecking ball Tom Wilson - a player who might give them some stylistic difference, but is also older, less productive, more injury-prone, and less impactful in process and result-driving. Sure, it's something different, but it's not the jolt in expected impact that the Raptors got three years ago, if any at all.
Realistically, there's no player who can add value to Toronto in a way that replicates the Kawhi trade, and if there was, the Maple Leafs wouldn't have the leverage to acquire them so long as the biggest hockey market on the planet keeps putting all of their core players on the proverbial trade block and puts Kyle Dubas in the "needs to make a move" seat. They're also not in a spot where those players have to be moved right now anyway. As frustrating as it was to see Toronto take yet another first round exit, one would have trouble placing their failures on the core this year - maybe a year ago we have this conversation about Mitch Marner given past playoff failures that resembled DeRozan's for the Raptors, but he stepped up this year. Auston Matthews was great in this series, and has had good series before. Tavares, who is probably the closest to "worth moving at for the right price" at the moment simply due to the age curves, stepped up in the second half of the series and was a ref whistle away from four goals in the last three games of the series. Nylander has routinely shown up in the preseason, as much as he is criticized by pockets of the city.
Morgan Rielly just signed a long-term extension, had a strong regular season, and stepped up in key moments in the playoffs. He'd be the most DeRozan-like from a heartbreak and drama if traded standpoint, but it's not likely you're going to be able to flip him for Cale Makar or others in the tier of defencemen that would need to be up for discussion to get close to the Kawhi-Demar gap. All of this is to say that Toronto's top players weren't the ones who cost them this series - and if anything, there wasn't much series-costing to begin with this year. There weren't no-shows in big minute roles, there weren't an abnormal amount of costly gaffes, and they won the shot attempt, shot, expected goal, and actual goal battles in the series. They simply lost to a team coming off back-to-back Stanley Cup victories and looking primed to evolve into a dynasty, based on how they're handling the Panthers at the time of publish. This year's loss hurts because of how long it's been since they've broken through, but on its own, dramatic change would be making a mountain out of a molehill. This is especially true when the bar offered for that change is effectively unachievable; a poor retelling of history that misses key context of a situation, a team, and a sport.