I know we still haven’t reached that definitive end to the Kawhi Leonard trade saga for Toronto, but we’ve definitely had some key developments that tip the scales more in the Raptors’ favor. Toronto is just waiting on the formalities and behind-the-scenes dealings to bring back their 2019 crown jewel for a second run. Even now, as we inch closer to the 2026-27 NBA season and several months after this news first broke, it still feels a bit surreal to think that Kawhi Leonard is more than likely to be a Raptor once again.
The route to this point hasn't exactly been smooth sailing, but that’s hardly the Raptors’ fault. In fact, Toronto’s position as the consensus top suitor to acquire Kawhi Leonard after it became clear he wasn’t returning to the Clippers quickly made the rounds in NBA circles. Sure, there were other teams with reported interest: San Antonio Spurs (Kawhi’s other former home), Dallas Mavericks, and even teams like the Houston Rockets, Miami Heat, and Detroit Pistons floated as potential landing spots.
But none had quite the same tangibility or ability to pull off an offer as Toronto did.
Now, with the Clippers at a significant draft asset disadvantage following league-issued penalties, the assets going back in the deal look even more enticing. Should the deal move forward, the Clippers will add a 2031 and 2033 first-rounder, a 2027 first-round swap, and two second-round picks in 2030 and 2033.
Even before the league confiscated their draft capital, it was clear that LA's best move would be to extract the most tantalizing picks in any Kawhi trade. On that point, Yossi Gozlan of the Third Apron Podcast recently pointed out that Toronto may have just been in the best position to reward the Clippers with that dream.
Raptors offered Clippers top draft value among a select group of Kawhi trade suitors
Gozlan said (YouTube link here): “I think they found the best trade partner with the Raptors in my opinion in terms of trying to get the best pick value in the future. It's not by much. The Mavs, it's mainly okay. They have Cooper Flagg, so they could be very good later. The Spurs are the Spurs. But the Raptors are still pretty good. They have Scottie Barnes, but it's worth noting that first first round pick won't come in until Kawhi finishes his 20th year. Maybe he's still in the league by then? He's an all-time great. They have a lot more longevity now. A lot of players that good play into their 20th year or so. So, I think given the options that they had, which is like pretty thin from the reports of where Kawhi wanted to go, I think they [Clippers] got, they extracted really like as much value as they could in a with a very tight amount of options they had available to them.”
As a Raptors-focused fan site, this doesn’t exactly paint the most advantageous picture at face value, since the focus is mainly on the high-upside potential of the Raptors’ picks heading out to LA. Despite the Raptors being in a position where they could have held back, especially now that the investigation has concluded and given them a bit more leverage — they were determined to go all-in with this core alongside a returning Kawhi Leonard. And it was largely this bold splash alone that has positioned the Raptors among the top East contenders.
The Clippers likely saw a franchise still in search of that defining factor to help push them over the hump again after a commendable effort in the 2025-26 campaign. As the guys on the podcast later discussed too, LA cashed in at just the right moment to maximize the Klaw’s value.
A 35-year-old Kawhi Leonard may come with a host of concerns, but you don’t trade this kind of pick value unless you have a bold, ambitious vision for the trade. Sure, there’s a chance these distant picks could come back to haunt the Raptors a little bit, but that’s a gamble you’re simply willing to take if you’re Toronto.
And no matter how you view it, this was perhaps the Raptors’ biggest edge in convincing LA to agree on a deal — aside from everything else working in their favor.
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