On September 4th, 2025, Kawhi Leonard found himself at the center of a potential salary cap circumvention controversy involving the Los Angeles Clippers. Following a report by Pablo Torre, John Karalis of the Boston Sports Journal revealed additional insights from a “high-level” source. According to this source, Leonard had entered into a side agreement with the company Aspiration, which granted him an additional $20 million in company stock, in addition to the $28 million he received from his original endorsement contract.
Karalis noted that the co-founder of Aspiration, Andrei Cherny, did not present the $28 million endorsement deal to the board of directors. Instead, he submitted it directly to Aspiration's executive team without prior consultation. This lack of oversight raised eyebrows within the organization, as management would have likely advised against the deal, viewing it as a “poor use of cash resources.” Despite Cherny's decision, Aspiration’s marketing and management teams opted not to utilize Leonard's services, citing a lack of “brand synergy” and a preference for partnerships with climate-focused influencers.
In addition to the endorsement deal, Karalis shed light on Clippers owner Steve Ballmer's $50 million investment in Aspiration. This investment was reportedly made with “light-to-no diligence” and at a price higher than what Oak Tree Capital Management had previously paid during the company’s fundraising rounds. Typically, significant investors like Ballmer would receive discounted share prices due to their potential to create positive buzz; however, he paid $11 per share, which was a dollar more than Oak Tree’s price.
The Clippers released a statement asserting that there’s “nothing unusual or untoward about team sponsors doing endorsement deals with players at the same time.” However, rival executives voiced concerns to Sam Amick of The Athletic, indicating that the combination of Ballmer’s investment in Aspiration and the magnitude of Leonard’s endorsement deal presents significant red flags. One general manager remarked, “This (sort of endorsement deal) does not happen,” illuminating the skepticism surrounding the situation.
The scrutiny surrounding Leonard is not unprecedented; the Clippers were previously investigated in 2019 due to allegations that Leonard’s uncle, Dennis Robertson, solicited improper benefits during Kawhi’s free agency negotiations. Reports emerged that Leonard was seeking an additional $15 million in endorsement money from the Toronto Raptors, while other sources indicated that “Uncle Dennis” was pursuing an ownership stake in the NHL’s Toronto Maple Leafs during discussions with the Raptors.
Nate Jones, an agent and marketer at Goodwin Sports, shared his thoughts on the matter via a Twitter thread, emphasizing that the Clippers, Ballmer, and Leonard might maintain plausible deniability unless concrete evidence of a quid pro quo arrangement emerges. Nevertheless, Kurt Helin of NBC Sports referenced Zach Lowe’s podcast, highlighting that the NBA’s Collective Bargaining Agreement permits the identification of cap circumvention through circumstantial evidence, especially if the terms of a deal cannot be rationally explained in another context.
As this situation unfolds, the implications for both Kawhi Leonard and the Los Angeles Clippers could be significant, particularly regarding compliance with NBA regulations and the integrity of player endorsement deals.
