In March 2023, LA Clippers owner Steve Ballmer invested almost $10 million into financial technology and sustainability services company Aspiration, according to legal filings reviewed by The Athletic and corroborated by a former Aspiration executive.

The previously unreported investment came 18 months after Ballmer’s $50 million investment in the firm now at the heart of an NBA investigation into whether Clippers star Kawhi Leonard made a side deal to circumvent the NBA’s salary cap, allegations first reported by the “Pablo Torre Finds Out” podcast last week.

Ballmer’s $10 million infusion into Aspiration came as the Los Angeles-based company was hemorrhaging cash, laying off employees and struggling to raise funds — and it came just three months after a $1.99 million investment by Dennis Wong, Ballmer’s college roommate and Clippers vice chairman, which was first reported by “Pablo Torre Finds Out” this week.

According to the podcast’s report, Wong’s investment was soon followed by a $1.75 million payment by Aspiration to Leonard, who signed a $28 million contract with the company in April 2022.

Ballmer’s 2023 investment was part of a fundraising round made up almost entirely of previous Aspiration investors, with Wong being the lone exception. The company hoped to raise $75 million in fresh money but came up nearly $9 million short. A vast majority of the shares were bought up by Aspiration co-founder Joe Sanberg and Ibrahim AlHusseini, another Aspiration board member. Sanberg later agreed to plead guilty to fraud charges brought by the Justice Department.

Ballmer’s first investment into Aspiration — a $50 million infusion alongside $265 million from OakTree Capital, a prominent financial firm — came in December 2021, three months after Aspiration signed a deal with the Clippers worth more than $300 million to be a founding sponsor of the team’s new arena and its jersey patch partner. The Clippers also signed an agreement to pay Aspiration more than $50 million for carbon offsetting toward the goal of becoming carbon neutral, according to multiple sources briefed on the deal.

Seven months later, Aspiration inked Leonard to a four-year, $28 million endorsement contract. Almost immediately, Aspiration struggled to make its quarterly $1.75 million payments to Leonard, and when the company was late with a payment that fall, Leonard’s agent, Mitch Frankel, reached out to company executives. 

In December 2022, Wong invested almost $2 million in Aspiration through DEA 88 Investments LLP. Days later, according to reporting by “Pablo Torre Finds Out,” Aspiration paid Leonard $1.75 million.

Three months later, according to court documents in a civil suit, Ballmer invested $9,999,997.92 in the company. Aspiration had been struggling financially, with just $12.2 million in cash as of Feb. 17, 2023 and running through more than $2 million a week. The Clippers declined to comment on the March 2023 investment. 

It’s unclear if Aspiration continued paying Leonard, who is listed as a creditor in Aspiration’s bankruptcy filings for $7 million, as are two companies representing the Clippers for a combined $50 million.

Long before the relationship between Leonard and Aspiration fell under public scrutiny, it caused confusion within the company itself, according to ex-employees who spoke with The Athletic. After Sanberg introduced the idea, members of Aspiration’s executive team believed Leonard’s deal, which was never announced publicly, held little value to the company. A former Aspiration C-Suite executive said that the deal “materialized essentially out of the ether.”

As part of the deal, Leonard also received $20 million in equity via Aspiration shares that came directly from Sanberg.

“I am personally contributing stock to Kawhi to make this partnership possible,” Sanberg wrote members of his leadership team in a May 2022 email obtained by The Athletic. “Aspiration’s CEO judged the deal to be not worth doing. For avoidance of doubt, any and all benefit to Aspiration from the Kawhi deal is being subsidized by my contributing my equity to make this happen.”

As part of the agreement, Sanberg also pressured the company to pay for fees incurred by Frankel, who did not respond to The Athletic‘s request for comment. 

While Aspiration executives initially traded ideas on how to incorporate Leonard in marketing campaigns — including in collaboration with Drake, a celebrity client and endorser — it never did so. One executive believed the famously laconic Leonard did not fit as a spokesperson. 

The contract specified that Leonard would, among other asks, participate in one eight-hour day of production, one four-hour day of public relations, two one-hour community service events, one five-minute segment per week “in conversation with (Clippers) Coach Ty Lue” while he sat out the 2021-22 season recovering from an injury, “five organic comments/likes/RTs as requested by Aspiration” and three off-court projects.

But the deal, which allowed Aspiration to terminate it for cause or if Leonard was no longer playing for the Clippers, also gave Leonard sign-off on the requests and allowed him to refuse to do anything “not consistent with his beliefs.”

Emails between Aspiration executives obtained by The Athletic reflected confusion and frustration with the contract. One marketing executive emailed that the deal had “pretty big flags” while bemoaning that it only guaranteed Aspiration one eight-hour production day, adding that Leonard’s lack of social media presence would “significantly hamper” the company’s ability to extract value from the deal.

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 contract was, however, much richer than Aspiration’s deals with other endorsers, according to the former executive who related that Leonardo DiCaprio and Robert Downey Jr. both received less than $2 million in equity, while Drake invested $4 million but also received carbon offsets.

Leonard never publicly promoted the company.

In March 2025, Sanberg was arrested and Aspiration filed for bankruptcy. Sanberg has agreed to plead guilty to federal charges of defrauding investors for $248 million. His next plea hearing is next week. An attorney for Sanberg declined to comment.

In August, the Securities and Exchange Commission alleged that Sanberg inflated the company’s revenue and duped investors, using Aspiration shares to take out more than $100 million in personal loans. The SEC’s complaint pointed specifically to two investors, including one who bought $50 million in shares between September and December 2021.

Aspiration employees said that Sanberg built and maintained a relationship with Ballmer to convince him to invest in the company. During a deposition last October, when the Aspiration co-founder was asked whether he was the one who landed Ballmer as an investor, Sanberg invoked his fifth amendment rights.

“They conned me,” Ballmer told ESPN last week. “I made an investment in these guys, thinking it was on the up and up, and they con me. At this stage, I have no ability to predict why they might have done anything they did, let alone the specific contract with Kawhi.”

Last week, the NBA announced it had hired law firm Wachtell, Lipton, Rosen & Katz, which has previously conducted league investigations into the Clippers and Phoenix Suns, to determine if Ballmer and the Clippers used Aspiration to circumvent salary cap restrictions. Ballmer has denied wrongdoing and said that aside from introducing Leonard to the company, he did not know anything about Leonard’s endorsement contract. 

If, after the investigation and a ruling by an independent arbitrator, NBA commissioner Adam Silver determines the Clippers broke league rules, he has the ability under the collective bargaining agreement to punish the team and Ballmer by docking draft picks, implementing fines and even voiding Leonard’s deal. 

At a news conference Wednesday following an NBA board of governors meeting, Silver  said he will look for more than the “appearance of impropriety” to penalize the team, adding that the burden of proof is on the league.

“I think the goal of a full investigation is to find out if there really was impropriety,” Silver said. “In a public-facing sport, the public at times reaches conclusions that later turn out to be completely false. I would want anyone else in situations Mr. Ballmer is in now — and Kawhi, for that matter — to be treated the same way I would want to be treated if people were making allegations against me. We’re not a court of law at the end of the day, either.”

(Photo of Steve Ballmer by Jayne Kamin-Oncea-USA TODAY Sports)