The Kawhi Leonard controversy is showing no signs of fading. The Los Angeles Clippers and owner Steve Ballmer are again under scrutiny after journalist Pablo Torre uncovered fresh details linking Leonard’s endorsement deal with the bankrupt financial services company Aspiration to possible salary cap violations.
According to Torre’s reporting on his “Pablo Torre Finds Out” podcast, a $1.99 million investment in December 2022 by Clippers vice chairman Dennis Wong preceded a $1.75 million payment to Leonard from Aspiration. Records indicate the transaction was marked as “critical” by the struggling company, which laid off employees that same day. Former employees told Torre the timing of Wong’s investment was “beyond shocking,” given that Aspiration was already bleeding money.
The spotlight intensified when it was revealed that Ballmer invested nearly $10 million in Aspiration in March 2023. This came just months after Wong’s transaction and after Leonard’s endorsement deal was already raising eyebrows inside the company. Ballmer had previously poured $50 million into the same firm alongside OakTree Capital, shortly after Aspiration signed a $300 million sponsorship agreement with the Clippers.
Steve Ballmer’s investment adds weight to questions surrounding the Clippers
Internal documents reviewed by The Athletic and Torre’s reporting describe Leonard’s contract as unusually lucrative. Especially when it's compared with other endorsers such as Leonardo DiCaprio and Robert Downey Jr., Leonard’s deal promised $28 million in cash and $20 million in equity. However, employees questioned its marketing value and described the agreement as arriving “out of the ether.”
The Securities and Exchange Commission has since accused Aspiration co-founder Joe Sanberg of defrauding investors of $248 million. Leonard is now listed as a creditor in the company’s bankruptcy filings for $7 million.
The NBA has hired law firm Wachtell, Lipton, Rosen & Katz to investigate whether the Clippers and Ballmer used Aspiration to sidestep league rules. Ballmer has denied wrongdoing. The Clippers owner says he was misled by company executives and had no involvement in Leonard’s contract.
Commissioner Adam Silver has stated that the league will look for more than the appearance of impropriety before issuing penalties. Potential sanctions could include fines, loss of draft picks, or even voiding Leonard’s deal. For now, the Clippers face growing scrutiny. Especially as Torre’s reporting continues to reveal new details that cut to the core of their relationship with Leonard.
