Kawhi Leonard reportedly made requests to Raptors in 2019 that ‘line up almost perfectly’ with Clippers controversy

As the NBA begins its investigation into whether the Los Angeles Clippers circumvented the league’s salary cap by setting up a lucrative “no-show” endorsement deal for franchise superstar Kawhi Leonard in 2021, a new report claims that Dennis Robertson, Leonard’s uncle and representative, sought similar impermissible benefits back in 2019.

Leonard was on top of the basketball world that summer. He’d just led the Toronto Raptors to their first NBA championship, winning his second NBA Finals MVP trophy along the way, and was entering unrestricted free agency at age 28, poised to cash in with a new deal to carry him through his athletic prime. The race for Leonard’s services came down to three teams: the incumbent Raptors, who could offer him the longest and largest total contract, and the Lakers and Clippers, who could offer the Moreno Valley native and San Diego State product an opportunity at a California homecoming.

The bidding for Leonard’s services became contentious. League sources later told Adrian Wojnarowski and Zach Lowe, then of ESPN, that as part of the recruitment, Robertson had “requested benefits outside the boundaries of the salary cap” — one eyebrow-raising aspect of a whirlwind summer of activity that prompted the league’s Board of Governors to vote to implement stricter rules against tampering and salary cap circumvention. Ultimately, Leonard opted to sign with the Clippers, who simultaneously swung a blockbuster trade with the Oklahoma City Thunder to land Paul George, an All-NBA running buddy on the wing, in exchange for a slew of draft picks and a budding young guard named Shai Gilgeous-Alexander.

According to Sam Amick of The Athletic, the NBA later “conducted a formal investigation of the Clippers … after complaints surfaced that Robertson had asked for improper benefits during the free agency process,” and found no evidence that the Clippers had granted any such requests in the process of signing Leonard. Multiple sources did tell Amick, though, that Robertson had made those asks to both Lakers governor Jeannie Buss and Raptors brass … and on Tuesday, Bruce Arthur of the Toronto Star reported, citing “multiple sources with knowledge of Toronto’s contract negotiations with Leonard in 2019,” that Robertson’s requests to the Raptors “line up almost perfectly” with what journalist Pablo Torre reported last week that Leonard received from Aspiration, the now-bankrupt former Clippers sponsor at the center of the controversy.

From Arthur:

According to those sources, who were granted anonymity in order to speak freely about the negotiations, Robertson’s list was long, and absurd. It included a trade for George, which featured an exorbitant price tag. It included a slice of ownership of the Toronto Maple Leafs, which Robertson was told was impossible.

But two details stand out, in retrospect. One, Robertson asked for ownership stakes in outside companies: not just the Leafs, which he seemed to believe was separate, but with other companies with whom MLSE had a relationship. And two, the Raptors were told they needed to match at least $10 million per year in extra sponsorship income. Teams are allowed to introduce players to team sponsors; teams cannot negotiate deals, and MLSE was aware of that fact.

But it didn’t end there. As one source put it, when told about all the corporate sponsors in Toronto who would be happy to have Leonard as a pitchman, his camp said, “We don’t want to do anything.” Raptors representatives said any sponsor would want to shoot ads or arrange appearances; Robertson reiterated Leonard didn’t want to do anything for the money.

That’s when the Raptors realized Leonard wasn’t asking to be introduced to Toronto’s lucrative corporate community; they were being asked to arrange no-show jobs, and arrange no-investment investments. MLSE rejected both proposals.

Neither Robertson nor Leonard’s agent, Mitch Frankel, responded to requests for comment.

Back in 2019, when asked about reports that his uncle had demanded interested suitors furnish him with beyond-the-CBA benefits, Leonard offered little.

“I didn’t read it. I don’t know how reliable it is,” Leonard said, according to Mark Medina, then of USA Today. “I have no knowledge of it. People make up stories every day.”

On his podcast, Pablo Torre Finds Out, Torre reported last week that Leonard had signed a four-year, $28 million endorsement agreement with Aspiration — described variously as a “sustainability-as-a-service” organization, “financial technology company” and “green banking company” that purported to offer carbon credits to offset consumers’ footprints by raising capital for the planting of trees — that didn’t require the six-time All-Star to actually do any endorsing of its products and services. John Karalis of the Boston Sports Journal later reported that Leonard actually had a second agreement, too — “a side deal with Aspiration to receive an additional $20 million in company stock … to be paid out from [Aspiration co-founder Joseph] Sanberg’s personal holdings in the company over four years,” bringing Leonard’s total potential compensation from the Aspiration deal to $48 million.

Leonard had agreed to an extension of his initial contract with the Clippers in August 2021. The following month, Clippers owner Steve Ballmer invested $50 million in Aspiration, and the Clippers announced a partnership with Aspiration valued at more than $300 million through 2043. Two months later, Leonard registered an LLC named KL2 Aspire; the following April, Leonard’s $28 million endorsement deal with Aspiration took effect.

In March 2025, Sanberg was arrested by the U.S. Department of Justice “on a federal criminal complaint alleging that he conspired to defraud two investor funds of at least $145 million,” and Aspiration filed for bankruptcy. Last month, Sanberg agreed to plead guilty to two counts of wire fraud.

In an interview with ESPN’s Ramona Shelburne last Thursday, Ballmer denied any wrongdoing related to salary cap circumvention. He said that Aspiration had asked the Clippers to make an introduction to Leonard, which the team did in early November 2021, but that the team was not involved in any subsequent dealings between Leonard and Aspiration, which he says “conned” him into making an investment that amounted to less than 3% ownership of the company.

When Shelburne asked Ballmer if Robertson, Leonard’s uncle and representative, had requested any outside-the-rules benefits of the Clippers, Ballmer said, “They know the rules — ‘they,’ meaning Kawhi and his representatives, including his uncle. We know the rules. And if anything’s not clear, we remind ourselves what the rules are and we make absolutely clear we’re going to abide by those rules and they understand them as well. And it’s important for them to abide by them, which they have.”

Last week, the NBA retained the law firm Wachtell, Lipton, Rosen & Katz to investigate the circumstances surrounding Leonard, Aspiration and the Clippers. The firm previously helmed the league’s investigations into claims of misconduct by then-Clippers owner Donald Sterling in 2014 and then-Suns owner Robert Sarver in 2022.