Kawhi Leonard trade rumors: Could the Spurs or Raptors bring him back?

Kawhi Leonard, for a multitude of reasons, is one of the most complicated trade candidates in recent NBA history. At this moment, we’re not even sure of the legality of a trade. The NBA is still investigating whether he and the Los Angeles Clippers circumvented the salary cap through his sponsorship agreement with Aspiration. If the NBA determines that they did, Leonard’s contract could be voided.

Even if it isn’t, it will need to be extended. Leonard has only one year and around $50 million left on his deal, and no team is going to be willing to pay the sort of assets it would take to trade for him without the assurance that he plans to stay beyond next season. That’s where things get tricky, because Leonard is known to be picky about destinations. According to Jake FischerLeonard is only open to extending with two teams (other than the Clippers), and they’re familiar ones: the Toronto Raptors and San Antonio Spurs.

Leonard spent the first seven enormously successful years of his career in San Antonio, winning Finals MVP in 2014 before forcing a trade in 2018. He wanted to get to Los Angeles at that point, but instead took a one-year detour to Toronto, picking up a second Finals MVP trophy while leading the Raptors to their first championship. He’s been a Clipper ever since, but his time in Los Angeles has been more disappointing than successful.

The Oklahoma City Thunder built a budding dynasty off the Paul George trade Leonard forced them to make. The Clippers have only reached the conference finals once, and it came with Leonard sidelined for the last two games of their second-round win over the Utah Jazz. Now Leonard is about to turn 35, and while he’s coming off one of his best seasonshe has a lengthy history of injuries that make him a tricky trade candidate. The Clippers kicked off a youth movement at the deadline when they traded James Harden for Darius Garland and Ivica Zubac for Bennedict Mathurin and a collection of picks that included No. 5 overall selection Keaton Wagler. The Clippers have said they plan to try to win with Leonard. Their actions point in another direction.

Toronto may have won it all with a Leonard rental in 2019, but it’s hard to imagine anyone trying to replicate that feat. The Clippers are only trading Leonard if they can get a substantial return, and a contract extension is a prerequisite for that sort of return. If the Raptors and the Spurs are the only teams he’s willing to extend with, then they’re the viable destinations. But what trades to make that happen look like?

How the Raptors could trade for Kawhi Leonard

The Clippers will ask for Collin Murray-Boyles, the No. 9 overall pick in last year’s draft and a standout, multi-positional defender. That’s probably going to be a sticking point in negotiations. The Raptors need him for the eventual Leonard-led version of their team, and they know Leonard has limited his own market enough that the Clippers can’t exactly drum up a bidding war. If Toronto is the only game in town, the Clippers extracting an asset as prized as Murray-Boyles would be an uphill battle. Still, considering they’re built around two offensively inclined guards in Garland and Wagler, landing Murray-Boyles would be an enormous victory for the Clippers, so they’ll definitely try.

Even without him, Toronto has more than enough in the way of assets to make a deal like this happen. The Raptors control all of their own first-round picks. That’s more than enough immediately, especially for a Clippers team that still owes control over three first-round picks out thanks to the 2023 Harden trade and could lose more in the Aspiration investigation. Multiple first-round picks, especially ones that convey after the expiration of the new lottery rules in 2029, should be plenty.

Where things get complicated is matching salary. Most of Toronto’s money is bad. Brandon Ingram has more than $80 million left on his contract over the next two years. He disappeared in the playoffs even before he got hurt. Immanuel Quickley, at $32.5 million per year, is paid as a high-end starter when he might be best-suited as a luxury backup. Jakob Poeltl is about to start an extension that will pay him at the top of the non-star center market when he’s no longer even a starting-caliber big.

The Clippers aren’t going to want to touch any of them. While the Raptors could technically match Leonard’s salary using the expiring deal of RJ Barrett and the combination of Gradey Dick and Ja’Kobe Walter, doing so would create a first-apron hard cap that Toronto couldn’t realistically deal with. As of this writing, the Raptors have only $5.3 million or so in space beneath the first apron, and they would not only need to duck it by enough to fill out the roster, but, given Leonard’s injury concerns, also leave themselves enough room to pay for playoff-caliber depth. To avoid a first-apron hard cap, the Raptors would have to send out more money than they take back. That means including at least one of Quickley, Ingram or Poeltl.

Ingram is probably the least objectionable of the three. He has only two years left on his deal, and trading Leonard would create a hole for the Clippers at small forward. Maybe they’d take him. Maybe they’d have to loop in a third team. But the reality is that Toronto would have to pay the fair asset price for Leonard, as well as the bad contract tax on top of that, to whoever takes on that less-than-desirable money. All in all, that could exhaust most of Toronto’s draft capital.

Is that even worth it to a team that just lost in the first round for someone who is about to turn 35? Toronto would have to be extremely confident in both Leonard’s health and its ability to build a contender around him afterward. Neither is a sure thing.

If the Raptors did pull it off, though, Leonard would represent the ideal teammate for Scottie Barnes. This postseason proved how lethal Barnes could be as a primary ball handler. Most of the star teammates the Clippers could find to support Barnes offensively would take the ball out of his hands and hurt the Toronto defense. Leonard does neither. He’s a tough shot maker who could handle crunch time while leaving the possession-by-possession load to Barnes and others. The version of him we saw last year would be lethal next to Barnes, and that alone would make this a deal worth considering.

Could the Spurs really bring back Kawhi Leonard?

Let’s start here… would Saint Anthony really want this? There might not be a single player in all of basketball less popular in his former home than Leonard, which is an astounding thought considering the championship he helped them win. When Leonard played a road game in San Antonio in 2023, for instance, the booing got so bad that then-coach Gregg Popovich had to grab a microphone and tell the fans to stop.

Even now, years later, we don’t fully know what went into Leonard’s breakup with the Spurs. There appear to be reasonable grievances on both sides. When Leonard won Finals MVP in 2014, the Spurs still made him wait a year for his max rookie extension to preserve cap space to sign LaMarcus Aldridge. When Leonard played only nine games in the 2017-18 season, there were disagreements over how to manage his health, with concerns about both his knee and his quad. The Spurs seemingly thought Leonard was healthy enough to play. Even Tony Parker took a jab at him in the press.

Whether the relationship is salvageable, we can’t say for sure, though Leonard signaling a willingness to extend with the Spurs suggests he’s at least open-minded. As for the fans, well, Leonard said it himself on the night of the infamous booing. “If I don’t have a Spurs jersey on, they’re probably going to boo me the rest of my career.” The thought of him wearing a Spurs jersey again feels slightly more realistic today than it did back then.

“Slightly” is the operative word here, because like the Raptors, the Spurs would have real trouble making the money work. Just technically matching the salary is entirely doable, especially since the Spurs are roughly $40 million below the luxury tax at the moment. Devin Vassell and Keldon Johnson alone for Leonard would be a legal trade. The questions start to emerge in the years to come. Victor Wembanyama’s inevitable rookie extension will kick in for the 2027-28 season. Stephon Castle follows a year later, then Dylan Harper. Leonard would fit on to the books this season. He wouldn’t fit for the long haul. At least, unless they were able to move De’Aaron Fox elsewhere.

That’s the salary slot that makes any of this possible. Leonard will make just $800,000 more than Fox this season, but Fox has three more max seasons left on his contract afterward. If the Spurs could sign Leonard to a two-year extension, they could solve their “three guards for two starting slots” dilemma and be done with Leonard’s next deal before it overlaps with Harper’s rookie extension. That’s the scenario in which this makes financial sense for the Spurs.

There is no universe in which the Clippers take Fox with Garland and Wagler on the team, though, and finding him a home feels almost impossible right now. The game of point guard musical chairs is well underway, and the music is about to stop. Four consecutive point guards were selected in the middle of the lottery on Tuesday. LaMelo Ball just took up the Minnesota slotand Coby White was re-signed at a starter’s salary to replace him. The Miami Heat just traded for Giannis Antetokounmposo their books are probably too tight.

Maybe the Chicago Bulls would be interested? The Phoenix Suns for a hodgepodge of iffy contracts? Would the Milwaukee Bucks just want a big name to try to stay competitive in the post-Antetokounmpo era? Finding Fox a new home after the Finals he just had, and with the contract he’s about to start, feels like a pretty tall order.

It’s a shame, too, because aside from being a fun homecoming story, it wouldn’t exactly be difficult to imagine Leonard fitting onto this roster in basketball terms. Leonard isn’t the offensive organizer Fox is, but he’s a stone-cold late-game killer who could keep the San Antonio offense afloat while Harper grows into the All-Star point guard we all assume he can be. Size at the forward slots was a real concern for the Spurs in the postseason against the Thunder and the New York Knicks. Leonard addresses it. He can guard anyone.

The Spurs have more than enough draft capital to make a trade of this size, with an incoming pick from the Atlanta Hawks next season, followed by a handful of valuable pick swaps in the years that follow and culminate with a potentially very valuable swap with the Sacramento Kings in 2031. San Antonio has plenty of young players who would interest the Clippers as well. Carter Bryant’s defense would be a very nice counterbalance to the offense-centric Garland-Wagler backcourt in Los Angeles. If he’s off the table, Vassell is at least a reasonably young, proven starter who can fit on most rosters.

But we live in the apron era. The CBA is more restrictive than it has ever been, and the Clippers just can’t justify paying Fox and Leonard long-term max deals, with their young players expecting paydays in the years to come. The Western Conference can breathe a sigh of relief, because a healthy Leonard might’ve made San Antonio unbeatable.