Kawhi Leonard will be in his final year of the three-year $149.5 million extension. The latest reports reveal the 2x NBA Champion is only open to extending with two former teams apart from the Clippers. The San Antonio Spurs are in the running and can bring the Finals MVP back amid the situation with De’Aaron Fox, after a disastrous Finals performance against the Knicks.

“The Spurs obviously have the asset value to do this (trade for Kawhi Leonard),” said insider Sam Quinn on the Third Apron podcast. “I’m sure the Clippers would love Carter Bryant, and I’m sure the Spurs would say ‘Absolutely not.’ But the Spurs obviously have so much draft capital that, like the 2027 Hawks, decent pick, especially in the flattened lottery era. 2031 Kings, you’re obviously always very eager to have that. In 2030, they have the double swap rights with the Mavericks and the Timberwolves. Very, very interesting pick.

“Like they have such good draft capital that if they could just figure out the Fox thing. Yeah, of course, they could get Kawhi. And then it’s just a matter of, do you want Kawhi? Yeah. And I personally think at the right price if you could move Fox, I probably would [trade for Kawhi].”

Trading for an expensive player like Leonard ($50.3 million in 2026–27) would require the Spurs to rearrange their cap sheet. Fox’s $221.7 million deal over four years limits the flexibility needed to absorb Leonard’s $50.3M salary, forcing San Antonio into a binary choice: retain Fox or pursue Kawhi.

It also presents the opportunity for San Antonio to move on from Fox’s contract, especially after the emergence of Dylan Harper from the bench. While the front office has publicly denied any tension surrounding Fox, the contractual math quietly makes that denial harder to sustain.

Devin Vassell’s ($27.5 million) and Keldon Johnson’s ($18 million) contracts could match the contractual obligations, but the Clippers would want more than that.

The CBA is also more restrictive than ever, which will make it difficult for the Spurs to manage the high-paying contracts of Kawhi Leonard and De’Aaron Fox.

Wembanyama’s rookie extension kicks in for the 2027–28 season, followed by Stephon Castle and then Dylan Harper- a compounding wave of max-level commitments that leaves no room to straddle the Fox decision.

Moving Fox elsewhere and acquiring Leonard isn’t just a trade preference- it’s a structural necessity if the Spurs want to build around Wembanyama before that window closes.

Leonard’s return would pair a two-time Finals MVP at a viable age alongside Wembanyama at his peak- but only if San Antonio moves Fox before those extensions stack. The Spurs’ championship window has a timeline, and that timeline runs through this offseason.

Plus, the situation in SA carries historical weight that makes the decision harder, not easier. The Spurs made Leonard wait a full year for his max rookie extension despite winning Finals MVP in 2014, a handling of his value that mirrors the current cap tension, where difficult roster choices are once again being deferred rather than confronted.

Then came the eventual departure, where the Spurs believed Leonard was healthy enough to play, but he wasn’t. Those unresolved wounds don’t disappear with a phone call.

Both sides must face the past, and the Spurs need to show by their actions, not by ignoring it, that the organization has changed.

Reunion with the Raptors for Kawhi Leonard

Six years after winning the championship, Toronto is once again interested in bringing Kawhi back. NBA analyst Jake Weinbach reported that a trade package centered around Brandon Ingram and some picks would be the option for the Raptors.

Ingram arrived at last year’s trade deadline and later received a 3-year, $120 million contract extension.

An average of 21.5 points per game on 47.7% field-goal shooting and helping the Raptors reach the playoffs for the first time since 2022 would mean it was a success.

This aligns with Jake Fischer’s reporting. The Clippers and Kawhi Leonard appear not to be on the same page, and Leonard would sign an extension with either the Raptors or the Spurs.

The Clippers must first decide whether to extend or move on- and only then do San Antonio and Toronto enter the picture. For the Spurs specifically, that window may be narrower than it appears.

Once the rookie extensions begin and Fox’s contract complicates the cap, the math that makes a Kawhi reunion feasible today becomes the math that makes it impossible tomorrow.