The Raptors’ seemingly endless wait for Kawhi Leonard could finally be over soon—although the fact that the NBA disputed ESPN’s reporting that it “has found no evidence showing LA Clippers owner Steve Ballmer funneled money through team sponsors to pay Kawhi Leonard in order to circumvent the salary cap” complicates the situation once again.
But even when the trade finally goes through, there are a lot of question marks. The biggest one is Kawhi Leonard’s health, which led The Hoop Collective’s Brian Windhorst, Tim MacMahon, and Vince Goodwill to all take the under on the Raptors for the 2026-27 season. The over/under was set at 45.5 wins.
“I think they overachieved last year,” MacMahon said on the August 18 episode. “Even if Kawhi is there, how many games—you know, is he playing 65? Is he playing 60? I don’t know, so I’ll go under here.”
Windhorst also noted, “Let’s say they get Kawhi. If he’s the player he was last year, that’s amazing. But it’s a huge unknown.”
After the Raptors were willing to spend pretty much their entire offseason in limbo for him despite the health concerns, doubts about his availability, and the fact that he hasn’t won a playoff series in years, Leonard will have a lot to prove if he finally ends up with the Raptors. After some good individual season with the Clippers that haven’t led to much team success recently, he needs to prove that he can still be a reliable top-two player on a very good team.
Expectations for Leonard’s return to Toronto are high
2025-26 was a big season for Leonard individually. He averaged a career-high 27.9 points per game along with 6.4 rebounds, 3.6 assists, and 1.9 steals. He was named to the All-NBA Second Team.
However, it was also just the second time in the last six seasons that he played more than 60 games, and the Clippers didn’t even make it to the playoffs. They finished ninth in the regular-season standings and lost to the Golden State Warriors in the play-in tournament. From a team standpoint, it was another disappointing season during his overall underwhelming Clippers tenure.
Leonard’s time with the Clippers started well enough. They went to the Western Conference Semifinals in his first season and to the Western Conference Finals the year after despite losing Leonard to an ACL injury in Game 4 of the Semifinals. After that, the Clippers struggled to find success. Leonard missed the 2021-22 season and failed to lead his team past the first round in three consecutive seasons afterwards.
If he comes to Toronto, the Raptors desperately need to snap that streak of early playoff exits. Otherwise, trading unprotected first-round picks for him could look very bad very quickly. Once the trade is finalized, the Raptors’ front office still has work to do to turn the team into a legitimate title contender, but there’s a certain expectation that Leonard will elevate the current roster past a first-round series in his first season back in Toronto.
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