The Los Angeles Clippers and Kawhi Leonard are at a crossroads. The 34-year-old put together arguably his best individual season yet in 2025-26, but with his injury history, it all feels so mercurial. Kawhi and the Clippers are also wrapped up in an NBA investigation into his last contract, with questions abound regarding the legality of his sponsorship agreement with the now-defunct company Aspiration.
With No. 5 overall pick Keaton Wagler joining Darius Garland in the backcourt, a youth movement is afoot in Inglewood. Should the Clippers decide to hit the reset button, the Toronto Raptors are a team that has engaged in “real trade conversations,” per The Stein Line’s Jake Fischer. Leonard won a championship with the Raptors in 2019 and is reportedly open to signing an extension north of the border.
The Raptors and Clippers have held real trade conversations this weekend on sending Kawhi Leonard back to Toronto, according to the league sources.
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— Jake Fischer (@JakeLFischer) June 28, 2026
This Raptors-Clippers trade reunites Kawhi Leonard with Toronto
The Raptors are more inclined to trade Brandon Ingram and the two years, $82 million remaining on his contract, per Fischer. But RJ Barrett is straight up the better player and the better value, due $29.6 million on an expiring contract. If the Raptors can tempt the Clippers to take on Jakob Poeltl’s sunk-cost contract — four years, $104 million — that becomes a huge victory.
Toronto adds the halfcourt scoring engine it presently lacks while amplifying an already fearsome defense. The Clippers receive three unprotected first-round picks (2027, 2029, 2031) for their troubles, which feels like a great return for a player with Leonard’s durability concerns. Even if it means eating the Poeltl contract.
Why the Clippers say yes
The Clippers can view R.J. Barrett as short-term help with designs on freeing up cap space next summer. Or Los Angeles can view him as an extension candidate who complements the Garland-Wagler backcourt as a physical downhill scorer who can handle tough assignments on defense, hit spot-up 3s and provide the Clippers with much-needed rim pressure from the wing in lieu of Leonard.
There isn’t a wrong strategy there. Barrett has limitations as a ball-handler and facilitator, but those are mitigated next to a couple high-feel guards like Garland and Wagler, who will spam pick-and-rolls and stretch the floor with their shooting. The Clippers can focus on getting Barrett to his spots, empowering him to attack decisively and finish, rather than asking him to freestyle, which is when he runs into problems.
It is perhaps easier to build a package around Ingram’s $40 million salary (and not take on the Poeltl contract), but Ingram feels like a potential negative fit with L.A.’s core. Not nearly enough strength or consistency as an off-ball scorer and decision-maker.
Poeltl’s contract is bad, but the Clippers are getting three first-round picks for Leonard on an expiring contract. He’s in his mid-30s with the longest injury ledger of any star in his age bracket. That alone carries massive long-term upside.
While it’s fair to look at Poeltl and the shelf life of that contract with extreme skepticism, here’s the simple truth: he would start at canter for the Clippers, a team in need of viable depth at the position after trading Ivica Zubac. Poeltl can set screens for L.A.’s guards, crash the boards and protect the rim at a reasonable level. If he can turn back the clock even a little bit, maybe he becomes a tradeable asset in a couple years. A sub-$20 million contract, in this NBA economy, does not qualify as an albatross.
Why the Raptors say yes
The Raptors in 2026 are very different than the Raptors in 2019, but also, there are serious parrallels. Before the Raptors traded for Kawhi the first time, it felt like Toronto had stagnated. The DeMar DeRozan-Kyle Lowry core was stuck in competitive no-man’s land — a winning team in the regular season but woefully unequipped for a deep run in the playoffs.
Toronto is once again a very solid regular season team. This is a top-five defense on paper, with a legitimate top-25 player in Scottie Barnes, an ascendent secondary star in Collin Murray-Boyles, and a talented supporting class. But Toronto simply does not have the offensive firepower to meaningfully compete with the Knicks, Celtics and the West heavyweights.
Leonard changes the equation. Can he actually string together two healthy seasons in a row? Fair question. Are the Raptors risking an imminent decline given Leonard’s history of lower-leg injuries and his advancing age? Also fair. But what Toronto needs is more shooting and more halfcourt shot creation. Leonard addresses both.
The Raptors really struggle to grind out offensive possessions when the pace slows. Leonard is perhaps the best iso scorer in the NBA — a mid-range machine with impeccable footwork and an unblockable high release on his jumper. Toronto can ride Kawhi late in close games while depending on their youth and tempo to hopefully carry them in the first three quarters.
Leonard still brings it on defense, too. He’s not the DPOY-caliber stopper he was in his prime, but Leonard’s unbelieveable blend of length, core strength and anticipation makes it incredibly hard for opponents to gain an advantage. He’s still lurking in passing lanes and blowing up rim attempts from the weak side.
Pair the two-time Finals MVP with a defensive anchor like Barnes, who can switch one-through-five and wreak havoc off-ball — not to mention CMB’s twitchy power on the interior and the additional length of Ingram, or the on-ball feistiness of Jamal Shead — and Toronto has a chance to field the best defense in the East.
The Raptors would be gambling on a tight two- or three-year window, in all likelihood. One that comes with very few guarantees. But Leonard has a chance to recapture the magic of that first title run and put Toronto in the same conversation as New York, Boston and Giannis’ Heat. The Clippers’ window has already closed. The Raptors know first-hand how spectacularly a gamble of this nature can pay off.
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