Steve Ballmer, Kawhi Leonard And A Fraudulent Tree Planting Company That Connects Them
Steve Ballmer, the owner of the Los Angeles Clippers and the richest owner among all of the “Big 4” professional sports teams (MLB, NFL, NBA, NHL), went on “SportsCenter” on September 4th to explain his side of the bombshell report that broke during that week. Ballmer and the Clippers have been accused of circumventing the NBA’s salary cap by using a now-defunct 3rd-party company named “Aspiration Partners” to funnel money to one of their players without the financial constraints that the salary cap has in place.
The player in question, Kawhi Leonard, had a highly public free agency back in 2019, where he was courted by both Los Angeles teams and his incumbent team, the Toronto Raptors. During that summer, Leonard and his representatives were reported as having “made demands that line up almost perfectly with what Leonard reportedly got from Aspiration” to the Toronto Raptors. Leonard’s camp relayed to the Raptors front office that they wanted at least $10M in extra sponsorship income but didn’t want to have to do anything to earn the money. He also demanded that the interested teams trade for Paul George, who Leonard identified as the co-star he wanted to team up with the most. In an NBA off-season that saw Kevin Durant, Kyrie Irving, Jimmy Butler, Anthony Davis, Russell Westbrook and Kemba Walker change teams, Leonard’s free agency drama shined the brightest. The NBA investigated the Clippers’ courtship of Leonard that summer, but ultimately ruled that there was no misconduct. Any Leonard potential scandal quieted after that and that stayed constant until this month.
In the past month, Leonard was discovered by Pablo Torre (the investigative journalist who first found out about this scandal) to have had two separate contracts through Aspiration; a $28 million deal spread over 4 years to promote the company on various social media platforms and $20 million in company stocks, totaling $48 million (Ballmer’s total investment in Aspiration was $50 million). Aspiration had hired other celebrities to promote their company, such as Robert Downey Jr and Leonardo Dicaprio, and they would agree in turn, to post on social media endorsing the company. Leonard, on the other hand, was discovered to not only have no social media posts about Aspiration (seen as a big red flag to Torre) but also no links to the company whatsoever, except for the financial ones, which were discovered when Aspiration went bankrupt and Co-Founder Joseph Sanberg plead guilty to fraud in March 2025. At this moment in time, there isn’t a legitimate reason as to why Aspiration paid Leonard $7 million a year (coined a “no-show” job by Torre).
During Ballmer’s interview with ESPN’s Ramona Shelburne, he said that Aspiration “defrauded me”. Under NBA rules, teams can introduce potential sponsors to their athletes, but that is as far as the NBA team’s involvement can be, which is what Ballmer alleged happened. Ballmer explained: “Where could any of this circumvention have happened? It didn’t, it couldn’t have. The introduction got made, and then they were off to the races, on their own. We weren’t involved.” Ballmer went on to say, “they conned me” and that he was “embarrassed” that he didn’t identify any red flags with Aspiration before deciding to invest in their company. The NBA has released a statement saying they are aware of the allegations and have begun to conduct their own investigation. If the Clippers are found guilty by the NBA of paying Leonard through Aspiration, there are precedents of fines, forfeiture of draft picks and suspensions of head decision makers.
In the weeks that have followed, the evidence brought forward by Torre has only made it harder for the Clippers to claim their innocence. In 2022, Clippers minority owner Dennis Wong invested $2M in Aspiration just days before a quarterly payment of $1.75M was due to Leonard. At this time, Aspiration had “no income, no pipeline of clients, and was really looking like it wasn’t going to be able to make payroll” according to a former employee, making a $2M investment from Wong very difficult to explain. In March 2023, Ballmer invested an additional $10M into Aspiration, once again just before a quarterly payment to Leonard was due. Former Aspiration CEO, Andrei Cherny, has refuted the claim that Leonard was signed to circumvent the salary cap, saying, “The contract contained three pages of extensive obligations that Leonard had to perform. And the contract clearly said that if Leonard did not meet those obligations, Aspiration could terminate the contract.” There is no evidence that Leonard met any of these supposed “obligations” that Cherny claims were in the contract. Ballmer was once again discovered to have invested another $21M in Aspiration in June 2022, two weeks before the first payment to Leonard was scheduled. In total, Ballmer and the Clippers have invested $118M into Aspiration over the course of 18 months.
If Leonard and the Clippers are found to have done what Torre is alleging, it will permanently stain both of their legacies. For Leonard, instead of being predominantly remembered for ending the Heatles or for winning the only championship outside of the United States, there’s a strong chance people first think of his injury plagued Clippers tenure which coincided with the biggest salary cap circumvention in league history. For the Clippers, an organization that has already dealt with a massive scandal in the 21st century and shares a city with one of the most famous organizations in sports, this could only add to their franchise history of irrelevance. Despite Ballmer building a state of the art new stadium (which coincidentally is hosting the all-star game this year), flying hundreds of fans to road playoff games and rebranding the team logo and jersey to try and spring them toward an era of basketball significance, those good faith efforts to grow the Clippers fanbase could all be undone if he’s guilty of funneling money to Leonard outside of league rules. It’s a shame that a first ballot hall of famer and an owner hell-bent on revitalizing Clippers basketball, will forever be linked to one of the biggest scandals in sports history.
The NBA investigation is ongoing, and there has been a strong push for the NBA commissioner, Adam Silver, to come down hard on the Clippers if they are proven to have done what Torre is alleging.
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