A Clear Breakdown of the Kawhi Leonard Catastrophe
Image Courtesy of Reuters.
By Sam Bergstrom
If you have entered the realm of sports media this past week, then you may know that the Los Angeles Clippers were just punished mightily for circumventing the National Basketball Association (NBA) salary cap.
There is a confusing amount of detail to this story, so here is a concise overview of how it all unfolded.
The Original Exposé
On September 3, 2025, Meadowlark Media journalist Pablo Torre published an episode of his investigative podcast “Pablo Torre Finds Out.” In the episode, Torre exposed how Los Angeles Clippers superstar forward Kawhi Leonard signed a $28 million cash endorsement deal with Aspiration, a sustainability-focused financial services company.
Torre acquired the endorsement paperwork, exposing how Aspiration struck the deal with Leonard’s business entity, KL2 Aspire LLC, on April 1, 2022. Despite Leonard being their reported highest-paid celebrity among the likes of Leonardo DiCaprio, Robert Downey Jr., and others, this deal was never made public; Leonard never marketed or endorsed Aspiration.
Another name found in the contract was Dennis Robertson, who was tabbed as Leonard’s “designated representative.” Robertson is both Kawhi’s uncle and longtime business manager, otherwise known as “Uncle Dennis.”
After Leonard initially signed with the Clippers in 2019, Robertson was investigated by the NBA for seeking prohibited benefits from teams such as “off-court endorsement money that could be guaranteed to Leonard if he played for that team.” The NBA found no evidence at the time that the Clippers had granted Leonard illegal benefits.
On March 31, 2025, Aspiration filed for Chapter 11 bankruptcy. In their bankruptcy filing, Torre showed how Aspiration still owed Leonard $7 million, which was more than they owed to the Boston Red Sox.
On his episode, Torre interviewed an anonymous former Aspiration finance employee. The employee was told by Aspiration that they had a “$28 million organic marketing sponsorship with Kawhi, and if I had any questions about it, essentially don’t, because it was to circumvent the salary cap.”
What’s more, Torre discovered that Clippers owner—and former Microsoft CEO—Steve Ballmer had invested $50 million into Aspiration in September of 2021, nearly a half year before Leonard signed with the company. After his investment, Aspiration became the “first founding partner” of the Intuit Dome, which Ballmer financed from the ground up as Los Angeles’s modern new home arena.
The Investigation and Repercussions
Not long after Torre’s episode launched, the NBA announced it would be conducting an investigation into this secret endorsement deal. The Clippers fervently denied all claims that they were circumventing the salary cap. Leonard himself stated this past April, “I think we’re going to be in the clear.”
“They conned me. I made an investment in these guys, thinking it was on the up and up, and they con me. At this stage, I have no ability to predict why they might have done anything they did, let alone the specific contract with Kawhi,” Ballmer said after the investigation began. “This was fraud and a bad investment. And I’m embarrassed by that.”
On June 1, Aspiration co-founder Joseph Sandberg was sentenced to 14 years in prison for defrauding investors and lenders of at least $248 million.
On September 2, the NBA concluded its investigation into the Clippers. Ultimately, they deemed that Los Angeles indeed violated the salary cap circumvention rules. Needless to say, the consequences are staggering.
The Clippers must now forfeit their 2029, 2030, 2031, 2032, and 2033 first-round picks. The team was fined $30 million, and Leonard was fined $700,000. Ballmer has been suspended for one year from league activities, and Robertson is banned from engaging with NBA teams for five years.
Clippers President of Business Operations Gillian Zucker and President of Basketball Operations Lawrence Frank were also found to be directly involved with these violations. Zucker is suspended without pay for one year, while Frank is suspended without pay for six months.
The Clippers organization and its personnel are also subject to a five-year compliance and monitoring program overseen by the league office.
The Further Findings
The independent law firm Wachtell, Lipton, Rosen & Katz uncovered critical findings during their Clippers investigation.
After Leonard’s initial 2019 signing, Robertson demanded that Clippers ownership orchestrate payments to Leonard via outside endorsements, which is illegal in the NBA. The investigation concluded that Ballmer and Zucker went along with Robertson’s demands.
Amidst the COVID-19 pandemic in June 2020, Zucker helped Robertson create the KL2 LBS LLC, and they reached out to three different companies for endorsement money: Boingo, Daktronics, and Lockton.
By August of 2021, those three firms all paid Leonard $18 million without any public knowledge of being associated with the Clippers or Leonard himself. According to the investigation, “the timing of the three endorsement agreements with Mr. Leonard coincides with each of the companies receiving multi-million dollar payments from the Clippers.”
In September of 2021, Aspiration entered a 23-year $382.5 million sponsorship agreement with the Clippers, plus a 23-year $72 million sustainability-services agreement for the Intuit Dome. As a supplement, Ballmer invested the previously mentioned $50 million.
On October 25, 2021, Zucker and Sandberg began negotiating the endorsement deal for Leonard, which went into effect on April 1, 2022. The total amount was $48 million over four years. That is, $7 million a year in cash—which equates to the previously mentioned $28 million —and $5 million a year in equity. Further details of how this deal came to fruition can be found in the full investigation report.
Also in April, Aspiration agreed to a four-year $28 million deal to fund the Kia Forum, which Ballmer owned. While Ballmer and Zucker claimed this was to offset the Forum’s carbon emissions, Sandberg “confirmed that the $7 million annual figure was tied to Aspiration’s contemplated payments to Mr. Leonard.”
The investigation also uncovers that the Clippers paid Leonard, Robertson, and other family members hundreds of personal expenses—tickets, gifts, travel—without properly deducting them from Leonard’s pay. Despite being previously warned and investigated, Los Angeles failed to report these improper requests to the NBA.
The Reactions
NBA Commissioner Adam Silver expressed this past Wednesday, “I am deeply disappointed by the flagrant violations of our rules and by the Clippers’ institutional and leadership failures that led to this misconduct. The severity of the penalties reflects the seriousness of the violations.”
“We vehemently reject the NBA’s findings, which are the result of a heavily biased investigation seeking to justify a predetermined narrative rather than facts and evidence,” the Los Angeles Clippers said in a statement.
Steve Ballmer’s attorney, David Kelley, expressed, “League counsel has acknowledged in our discussions that the league does not believe there was an agreement between the Clippers and Aspiration to funnel money to Kawhi Leonard. League counsel also agreed with the Department of Justice, the Securities and Exchange Commission, and a federal judge that Mr. Ballmer was a victim of Joe Sanberg’s fraud — not a participant.”
The Clippers agreed on a deal with the Toronto Raptors—the same team Kawhi won a championship with in 2019 before signing with Los Angeles—on June 30 to send Leonard back to his former team, but the trade has been on hold amid the investigation. Pending trade submissions by both teams, the trade is now on track to go through.
“I entered into my contract with the Clippers as well as the agreements in question in good faith, fully committed to fulfilling my obligations and with no knowledge of any intent on anyone’s part to circumvent the salary cap,” Leonard said through his new agent Harrison Gaines. “As I return to Toronto, I am focused on what I can control, closing this chapter, and moving forward with a clean slate.”
