Kawhi Leonard scandal: Steve Ballmer reportedly invested another $10 million into company he said 'conned' him

Another update has hit in the Kawhi Leonard scandal and it once again sounds quite bad for Steve Ballmer and the Los Angeles Clippers.

This time, The Athletic is reporting that Ballmer made another $10 million investment in 2023 into Aspiration, the fintech company that allegedly signed Leonard to a $28 million contract to promote the company, which he never did, as a way to circumvent the NBA's salary cap. The NBA has hired a law firm to investigate the allegations, with potentially severe repercussions.

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Ballmer had previously invested $50 million in the company at its founding stage, but has since defended himself by claiming that he was "conned" out of the money and denying all wrongdoing. Aspiration co-founder Joe Sanberg has pleaded guilty to to fraud charges brought by the Justice Department.

"The speculation is what it is," Ballmer continued. "Why did they do that? I don't know why they did what they did. And I don't know how different it is. And frankly, any speculation would be crazy.

"These are guys who committed fraud. Look, they conned me. I made an investment in these guys thinking it was on the up and up. And they conned me. At this stage, I have no ability to predict why they might have done anything they did."

Not helping his defense is a report that Leonard's camp asked for a deal from the Toronto Raptors very similar to what is being alleged.

It's unclear when Ballmer realized Aspiration wasn't on the up-and-up, but his subsequent $10 million investment came at a time when the now-bankrupt company was reportedly in dire straits, bleeding cash, laying off employees and failing

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Ballmer’s $10 million infusion into Aspiration came as the Los Angeles-based company was hemorrhaging cash, laying off employees and failed to reach a fundraising goal as it was foundering. It was also reported Thursday that Clippers co-owner Dennis Wong contributed another $1.99 million in that same 2023 period, which coincided with a $1.75 million payment to Leonard.

Via The Athletic, another Aspiration co-founder continued to dispute that Leonard had a no-show job, instead pointing to a clause that allowed the Clippers star to refuse to do anything “not consistent with his beliefs.”

When reached by The Athletic this week, Andrei Cherny, Aspiration’s co-founder and CEO until 2022, disputed that Leonard had a no-show contract. He said the beliefs clause is standard for celebrity endorsements and that the company could end the agreement if Leonard didn’t perform on his end.

“In the months of discussion among our executives before signing the sponsorship, I don’t remember conversations about the NBA salary cap,” Cherny said. “I signed the contract shortly before I submitted my resignation, but before I left there were numerous internal conversations about the various things Aspiration was planning to do with Leonard once the 2022-23 season began, including emails from the marketing team about their plans in just the week before my last day. I can’t speak to what was done or not done after I left — or why.”

The Athletic also notes that Leonard's endorsement contract gave him $20 million in equity for a promotion job he never did, much more than celebrity investors Leonard DiCaprio and Robert Downey Jr. and Drake, who all had under $5 million in the company.