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Come Fan with UsTuesday, August 4, 2026

How the Raptors are risking everything and nothing for Kawhi Leonard

By trading DeMar DeRozan to the Spurs for Leonard, Toronto is both aiming for higher peaks and allowing a retooling to arrive.

We all knew the Toronto Raptors needed real changes this summer after another painful ejection from the NBA playoffs at the hands of LeBron James and the Cleveland Cavaliers. Even if back in May there was an inkling that LeBron would leave the Eastern Conference, Toronto couldn’t run it back and expect to keep pace with the Celtics or 76ers. This was their year, and they blew it. Again.

But the only immediate change made was on the sidelines, where Dwane Casey — named Coach of the Year for Toronto’s season — was replaced by his assistant Nick Nurse. The Raptors couldn’t afford to chase any major free agents (though they retained Fred VanVleet) and didn’t openly shop any of their core players. As the molten core of the offseason cooled off over the past week, it appeared that the Raptors would bring the same team back with a new general and hope there was a post-LeBron window for Toronto.

There was one exception to the Raptors’ invisible summer, though: they were always mentioned as a team interested in the Kawhi Leonard trade circus. And now, they have reportedly traded for Kawhi, sending DeMar DeRozan, Jakob Poeltl and a 2019 first round pick to the Spurs.

This is both a huge risk for the Raptors and no risk at all.

How it’s a huge risk

Leonard is an unrestricted free agent in 2019, and has reportedly been set on relocating to Los Angeles. The Raptors could very easily lose Kawhi for nothing in one year. Between now and then, there’s no real guarantee Kawhi will be healthy enough to make a big impact for Toronto: he played just nine games last season due to the mysterious quad injury that broke his relationship with the Spurs.

Meanwhile, DeRozan is good. He’s made back-to-back All-NBA teams. He’s a big-time scorer who has become efficient from the field despite the lack of a reliable three-pointer. Part of Toronto’s excellence in recent years — a big part! — stems from DeRozan’s growth. Toronto will miss his contribution.

If Kawhi is still hurt, or if Kawhi leaves in a year, that loss will likely mean a severe drop-off for the Raptors. If it all goes sideways, Toronto is risking its run of three straight seasons with at least 50 wins and its 5-year playoff streak for a chance at being even greater.

This could be the move that finally gets the Raptors to the NBA Finals, or it could be the move that plunges Toronto back into lottery hell.

How it’s not a huge risk

That said, if Raptors president Masai Ujiri believes in Toronto’s young players as much as we think he does, is this much of a risk at all? You could look at the Leonard trade as a sort of salary cap dump of DeRozan’s hefty contract. DeRozan is due $85 million over the next three seasons, and between that and Kyle Lowry’s contract ($66 million over the next three years) Toronto is capped out.

If the Raptors’ fruitless postseason required major changes, either DeRozan or Lowry needed to be on the block. You can’t make truly major changes without moving one of those salaries. This trade accomplishes that, albeit in a deal for another All-NBA star who, should he stay, will require an even larger outlay.

We don’t know whether Toronto would have rather moved Lowry, is still seeking to move Lowry, is finding it impossible to move the older Lowry, or prefers to keep him despite the huge salary. DeRozan was clearly the easier of the two to trade. Again — and this bears repeating because so many fans discount how damn good DeRozan has become — DeMar has been voted one of the 15 best performers in the NBA in each of the last two seasons!

But if Ujiri believes that these Raptors reached their zenith with 59 wins and another spring sweep, and if Ujiri had trouble finding a path to move Lowry but was looking ahead to a retooling around the team’s younger players, then trading DeRozan was the best shot.

To do that and get at least one year of a top-5 player when healthy is incredible. If it works, the Raptors might have their best team ever and a conference champion. If the Kawhi experiment goes sour, the Raptors are in a retool and rebuild mode that seemed inevitable back in May.

Really, Ujiri can sell this move however he wants, and he can sell it totally dependent on what actually happens. If Toronto breaks the 60-win barrier and makes a run at the NBA Finals in a LeBron-less conference, this move was all about landing Kawhi. (You have to hope, for the Raptors’ sake, that such success would lead Leonard to remain in Toronto.) If Toronto falls flat, this move was a moon shot that opened the door for a needed retooling.

After LeBron exposed the Raptors in the playoffs again, change had to come to Toronto. Here it is. Now we watch to see whether the change will push the Raptors higher than ever before or start a major franchise reset.

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