Kawhi Leonard’s return to Toronto is already about more than the next three seasons.
The Raptors gave Leonard a two-year, $115 million extension with a player option in the second year, a deal that gives the franchise an immediate runway to chase a title while one of the league’s elite players is still in the fold. But the longer view around this partnership may stretch far past that window. According to NBA insider Jake Fischer, there’s even a chance Leonard’s second run with Toronto lasts beyond the 2028-29 season.
“Kawhi and the Raptors are thinking about the possibility of his second stint with the franchise not just lasting these upcoming three years, and there’s a thought that this player option could ultimately be declined for Kawhi and Toronto to continue this remarriage deeper beyond the 2028-29 season into the 2030s, into the next decade,” NBA insider Jake Fischer said on a BleacherReport livestream.
Leonard is 35 and has a long injury history, so expecting him to be the centerpiece of a contender deep into the next decade would be a stretch. Still, even if he isn’t carrying the load as the top offensive option by then, he could remain a useful piece alongside younger talent if his body holds up. He reportedly plans to retire with the Raptors.
For now, Toronto’s bigger task is figuring out how to build around Leonard and Scottie Barnes, the two players who give the roster its core. That means evaluating the current group, identifying the right fits, and deciding where the most urgent upgrades need to come.
RJ Barrett, who will be a free agent after this season, stands out as a possible trade chip. Jakob Poeltl’s massive contract has also become an issue, while Immanuel Quickley still has plenty to prove after missing last season’s playoffs.
There’s not much room for delay. The Raptors need to push this roster toward contention in the next three years, because if they don’t, the cost of landing Leonard - including two first-round picks and other assets - will start to look like a mistake.
And that’s the part that makes this return feel so layered. Leonard hasn’t played a game yet, but the path back to Toronto has already included the paused trade, the salary-cap circumvention investigation, and plenty of uncertainty. The hope now is for the noise to fade and for the Raptors to keep building off last season’s success with Leonard leading the way.
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