Kawhi Leonard $48 Million Deal Was Not To Help Circumvent the Cap, Says Ex-Aspiration CEO
Aspiration signed Kawhi Leonard to a $28 million endorsement deal, 10 times higher than what they paid Hollywood A-List actors.

Los Angeles Clippers star Kawhi Leonard (Image via FirstSportz)
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The NBA is still investigating all the allegations of salary cap circumvention leveled against Kawhi Leonard, the Los Angeles Clippers, and principal owner Steve Ballmer.
The investigative podcast, Pablo Torre Finds Out, revealed that the billionaire invested in Aspiration, which then signed the star forward to an endorsement deal, handing out $28 million in payments and $20 million in stock.
The former Microsoft CEO has denied these allegations, claiming that Aspiration had scammed him when pitching their business plan. He also claimed that the Clippers were the ones who introduced Leonard to the now-bankrupt company.
Since then, reports of the 2-time champion’s uncle, Dennis Robertson, making similar demands to the Toronto Raptors, but they did not agree, and that left Leonard to sign with the Clippers. Another allegation came in when Pablo Torre revealed that Clippers vice chairman Dennis J. Wong sent $1.99 million to Aspiration. 9 days later, the company then paid Kawhi Leonard $1.75 million.
In the midst of all this, the Athletic decided to get in touch with someone who was high up in Aspiration and managed to get an interview with its former CEO, Andrei Cherny. When asked about them helping the Clippers circumvent the salary cap, he said.
In the months of discussion among our executives before signing the sponsorship, I don’t remember conversations about the NBA salary cap.
Andrei Cherny said, as quoted in The Athletic
Cherny revealed to Mike Vorkunov that the deal with Kawhi Leonard was signed shortly before he resigned. Until he was there, he also reiterated that the company did not give the NBA star a ‘no-show’ deal, leaving a clause to cancel the contract if he did not perform.
Steve Ballmer invested another $10 million in Aspiration in 2023
Andrei Cherny’s comments could bring in another aspect to the NBA’s investigation. However, The Athletic managed to get their hands on court documents filed in a civil lawsuit that reveal another investment from Steve Ballmer.

Three months later, according to court documents in a civil suit, Ballmer invested $9,999,997.92 in the company.
Mike Vorkunov revealed in his article
The three months Vorkunov mentions is the time after Dennis J. Wong sent $1.99 million to Aspiration. When The Athletic reached out to the Clippers about this March 2023 investment, they declined to comment.
It is unclear if any part of this $10 million cash injection reached Kawhi Leonard, but the franchise’s representatives declining to comment might lead the NBA’s investigators to look into it.
Kawhi Leonard’s fate depends on independent arbitrator’s findings
Over the past several days, ‘evidence’ has been placed forward linking Kawhi Leonard’s $48 million endorsement deal with Aspiration to the Los Angeles Clippers. The problem for the NBA and its investigating arbitrator is that they have to link the star forward and Steve Ballmer’s investment in Aspiration as a method to circumvent the cap.
The current CBA allows the league and its arbitrator to use circumstantial evidence to come to a conclusion. The key aspect here is that the arbitrator has to find the link and establish that Ballmer and the Clippers somehow used Aspiration to pay Leonard.
Unless they, in this instance, the law firm Wachtell, Lipton, Rose and Katz, find that Ballmer and the Clippers are guilty, NBA Commissioner Adam Silver cannot do anything on his own.
He has the power to impose fines, dock draft picks, void Kawhi Leonard’s contract, or even ban him from the league. However, to do that, he has to wait until the law firm comes up with evidence that the salary cap circumvention took place.
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