Aspiration‘s Collapse and the Kawhi Leonard Deal Under Scrutiny
Aspiration, a financial technology company focused on enduring investing, filed for bankruptcy in March 2025 following the arrest of its founder, Andrei sanberg, who has agreed to plead guilty to federal charges of defrauding investors out of $248 million. The company’s downfall has triggered an NBA investigation into a potentially improper endorsement deal with Kawhi Leonard and the involvement of Los Angeles Clippers owner Steve Ballmer.
The controversy centers around a lucrative contract offered to Leonard, reportedly delivered to Aspiration already completed. Three Aspiration executives stated they “expressed concerns at the time regarding the high cost of the agreement and its lack of alignment with Aspiration’s brand and business strategy,” and that the deal “was not reviewed how other similarly sized transactions were.” They further asserted the deal was “not in the company’s best interest” and “remains so today.” The executives noted that while marketing efforts related to the deal were initially undertaken, they were later discontinued, indicating a lack of genuine support for the partnership.
The Leonard contract significantly exceeded the value of endorsement deals with other high-profile figures. Leonardo DiCaprio and Robert Downey Jr.both received less than $2 million in equity, while Drake invested $4 million but also received carbon offsets as part of his agreement. Notably, Leonard never publicly promoted Aspiration.
The Securities and exchange Commission (SEC) alleges Sanberg inflated the company’s revenue and used Aspiration shares to secure over $100 million in personal loans, deceiving investors in the process. The SEC’s complaint specifically highlights two investors,including one who purchased $50 million in shares between September and December 2021.
Evidence suggests Sanberg actively cultivated a relationship with Steve Ballmer to secure his investment in Aspiration. During a deposition last October, Sanberg invoked his Fifth Amendment rights when questioned about his role in securing Ballmer’s investment.
Ballmer has publicly stated he was defrauded by Aspiration. “I made an investment in these guys, thinking it was on the up and up, and they con me,” he told ESPN. He claims his involvement with Leonard was limited to an introduction, and he was unaware of the details of the endorsement contract.
The NBA has hired the law firm Wachtell, lipton, Rosen & Katz to investigate whether Ballmer and the Clippers used Aspiration to circumvent salary cap restrictions. If the investigation,and a subsequent ruling by an independent arbitrator,determine the Clippers violated league rules,Commissioner Adam Silver could impose penalties including the loss of draft picks,fines,or even the voiding of Leonard’s contract.
At a recent news conference, Silver emphasized the league’s commitment to a thorough investigation, stating he would seek to determine if “impropriety” occurred and that the league would not rely solely on “the appearance of impropriety.” He also noted the league’s standard of proof differs from that of a court of law, and that fairness would be paramount in the process.
