Kawhi Leonard continues to draw headlines for a variety of reasons, some of which are related to his on-court heroics, others pertaining to his off-court exploits.
More than half a decade after his arrival with the Los Angeles Clippers, the latest Leonard controversy has seen the Los Angeles forward's initial contract with his current employers come under scrutiny. Leonard's 2019 free agency drew plenty of interest, not only because of his talent as a player, but also because of the nature by which he and his entourage attempted to negotiate with organizations interested in landing his services.
A recent investigation into Leonard's arrival in Tinseltown appears to indicate that both he and Los Angeles worked with one another to circumvent league salary cap rules -- and line his pockets, in the process.
Here's what you need to know.
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Kawhi Leonard contract scandal
After leading the Toronto Raptors to the 2019 NBA title, Leonard was the hottest commodity on the free agency market. He yielded an impressive number of suitors, each hoping to secure the services of arguably the league's best player.
The Leonard sweepstakes centered on three teams: Toronto, who could offer him a longer and larger contract than anyone else, the Los Angeles Lakers and the Clippers.
Leonard reportedly sought assurances that extended far beyond the basketball floor. According to The Athletic's Sam Amick, Leonard's advisor and uncle, Dennis Robertson, requested that the various parties interested in landing Leonard's services offer him additional benefits.
Reportedly included in the negotiations between him and Robertson were ownership stakes in companies, corporate sponsorships and "no-show" endorsement deals that allowed for Leonard to collect millions in revenue without doing any actual work.
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Investigative journalist Pablo Torre looked into Leonard's free agency and eventual signing with the Clips. After parsing through legal documents and dozens of interviews with former Aspiration employees to unearth Leonard's reported involvement in the scheme, Torre found that Leonard and his employers devised a "fool-proof" system to secure Leonard an additional $28 million in funding. Additional Torre investigating found that Aspiration offered Leonard an additional $20 million on top of his initial $28 million nest egg, meaning he was due to collect $48 million.
The mechanism for Leonard to collect said resources was KL2 Aspire LLC, a company owned by Leonard. The company partnered with the Steve Ballmer-led firm Aspiration, a tree-planting company that went bust in March 2025.
According to Torre, Leonard's affiliation with Aspiration allowed the Clippers to circumvent the NBA's salary cap rules to fulfill Leonard and Robertson's demands for extra benefits. Payments from Aspiration were reportedly sent to KL2 Aspire LLC through Robertson.
Clippers owner Steve Ballmer denied the allegations during a Sept. 5 appearance on ESPN, saying he didn't know "anything about the court documents" that Torre had brought up and that he hasn't seen them.
"The speculation is what it is," Ballmer said. "I don't know why they did what they did. And I don't know how different it is, I really don't. And frankly, any speculation would be crazy. These are guys who committed fraud. Look, they conned me. They conned me. I made an investment in these guys."
Steve Ballmer:
— Oh No He Didn't (@ohnohedidnt24) September 5, 2025
"Pablo's podcast I don't know anything about the court documents on this. I haven't seen them and I don't know. The speculation is what it is. They conned me. I made an investment in these guys" https://t.co/5HqOZF5z9A pic.twitter.com/iqI1kYMZHL
Ballmer also broke down the timeline of the Leonard-Aspiration connection from his point of view, saying that Leonard had not even been introduced to Aspiration until two months after the alleged circumvention of the cap took place.
"They did request to be introduced to Kawhi. Under the rules, we can introduce our sponsors to our athletes, we just can't be involved. We made an introduction, that was in early November, well past when all of this happens," Ballmer said.
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What is Aspiration tree planting company?
Aspiration was a "tree brokerage" firm founded by Ballmer. The company landed endorsements from Robert Downey Jr. and Drake, both of whom were paid to publicly support Aspiration. The same couldn't be said about Leonard, who was offered $28 million "to circumvent the salary cap", an unnamed employee said.
"The single largest payment to an individual for marketing that Aspiration ever made has completely evaded all press. ... He didn't have to do anything," the employee added.
Aspiration filed for bankruptcy in March 2025. Leonard was listed as one of its creditors, with the company allegedly owing Leonard $7 million, according to legal documents examined by Torre.
Will Kawhi Leonard, Clippers be punished?
Shortly after Torre's investigation went public, the NBA announced that it was opening an investigation into Leonard and the Clippers' alleged actions. The league had previously looked into allegations that Los Angeles had offered Robertson impermissible benefits, clearing both the organization and the advisor of wrongdoing.
Torre's investigation appears to have all the makings of a smoking gun. If the league were to dole out a punishment, it likely would be severe for both organization and player alike. In 2000, the league found that the Minnesota Timberwolves circumvented salary cap rules to sign Joe Smith. Minnesota was summarily docked five first-round picks (two were eventually returned) and handed a $3.5 million fine (equivalent to around $6.56 million in today's money).
Then-Timberwolves owner Glen Taylor was suspended and then-Minnesota head coach Kevin McHale was forced to take a leave of absence, while Smith had his contract voided and his Bird Rights stripped away. Contemporary tampering violations have seen teams forfeit second-round picks, although given Leonard's prominence and the drawn-out nature of this controversy, it's unclear whether such a sanction would be deemed serious enough.
Kawhi Leonard contract
- Years: Three
- Contract: $149.5 million
Leonard agreed to terms on a three-year, $149.5 million deal ahead of the 2024-25 season. His latest deal is the third he inked with Los Angeles, following the three-year, $104 million contract he signed in 2019 and the four-year, $176 million extension he landed in 2021.
Clippers salary cap
Per Spotrac, the Clippers have upwards of $200 million tied up in cap allocations. Their -$48.96 million cap space is the 17th-highest mark in basketball.
Los Angeles currently sits $1.3 million inside the first apron. They have a little more than $13 million in second apron cap space, with Leonard and James Harden the team's highest earners at $50 million and $39.182 million a year, respectively.