Los Angeles Clippers owner Steve Ballmer invested nearly $10 million in Aspiration in March 2023 as the now-bankrupt company was bleeding cash, laying off employees, and struggling to raise funds, according to legal filings reviewed by The Athletic’s Mike Vorkunov and corroborated by a former company executive.

Ballmer’s previously unreported financial commitment came three months after Clippers co-owner Dennis Wong reportedly wired Aspiration just under $2 million and 18 months after Ballmer’s initial $50 million investment into the financial technology and sustainability services firm.

Aspiration was months late on a $1.75-million payment to Kawhi Leonard as part of its four-year, $28-million “no-show” endorsement deal with the Clippers star, Pablo Torre reported earlier this week on his podcast “Pablo Torre Finds Out.” The company apparently paid Leonard nine days after receiving the funds from Wong.

Ballmer’s 2023 investment was part of a fundraising round consisting almost exclusively of previous Aspiration investors, according to Vorkunov. Aspiration co-founder Joe Sanberg and another company board member reportedly purchased most of the shares.

Sanberg’s Aspiration co-founder Andrei Cherny, who was also its CEO before departing the company in 2022, said Friday that Leonard’s deal was not a “no-show” agreement. Cherny, whose signature is on Leonard’s $28-million endorsement contract, added he does not recall discussing the NBA’s salary cap with other Aspiration executives before he signed the deal.

With the many “hot takes” in the past 10 days about the Clippers/Kawhi Leonard, it’s been surprising (though maybe it shouldn’t be) that until now no reporter has bothered to reach out to me for the facts about that contract. This is what I told the NY Times/Athletic today: pic.twitter.com/VuhlM02fCQ

— Andrei Cherny (@AndreiCherny) September 12, 2025

Sanberg pleaded guilty in August to defrauding investors and lenders of more than $248 million.

The NBA hired a law firm to investigate allegations that Ballmer circumvented the salary cap by paying Leonard additional funds through a third party.

Ballmer has denied the claims against the Clippers and stated he was “conned” by Aspiration.