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 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.

https://www.nytimes.com/athletic/6624269/2025/09/12/clippers-steve-ballmer-kawhi-leonard-aspiration-investment-sponsorship/

38 comments
  1. So, did this investment come before or after Ballmer stated he was scammed? IIRC he didn’t delve too deeply into timelines, so maybe he didn’t comment at all on such details.

  2. Lmao Shelburne alluded to this as well and now it’s confirmed.

    So Ballmer was scammed out of his $50m but he invested $10 more millions into a company that couldn’t pay its bills and just laid off 20% of its staff and was under investigation.

    Ballmer has been exposed as a liar.

  3. In Lando Calrissian voice: *This deal getting worse all the time.*
    Clippers are cooked for sure.

  4. smh clickbait

    ballmer invested an additional $9,999,997.92 not 10m. sleazy “journalists” at it again

  5. It was really fun watching “reporters” run cover for the billionaire, only for every subsequent story to prove Pablo right lmao

  6. If silver doesn’t do anything about this it’s wraps. Would honestly be hard to care about the league anymore as a small market fan.

  7. So taking away how many picks will be a sufficient penalty? Cause fining isn’t going to do a thing.

  8. Dude Mark Cuban had a gotcha for Pablo. So what Dennis Wong made a payment that ultimately went to Kawhi, who made all the subsequent payments??? Uhh, Ballmer!

  9. > In March 2023

    Y’all will never guess when Kawhi was scheduled to receive his next payment after the December 2022 one that Wong’s investment covered…

    🙃

  10. Good heavens, man. This is so hilarious because the WCF appearance they have was without Kawhi. What was he circumventing the cap for?😂

  11. Looks like we found out who paid the rest of KLs money Mark. 

    “What about the other $6M?” Cuban, probably

  12. Pablo likely has so much ammunition that he’s just letting anyone who wants to engage make a fool out of themselves before he drops the nuke. All of these podcasters and talking heads are going to look moronic and we can cull their content from our lives.

  13. Pablo is the best at journalism cus he finds one little thing and it just opens up a huge can of worms. Forces other people to start digging too and even more comes out. Just a living legend

  14. So this entire company was propped up as tool for Ballmer and Kawhi to get around the salary cap. Incredible.

  15. Wong invested $1,999,999, I believe. Ballmer invested $9,999,998. An odd coincidence. This makes me wonder if there are any disclosure or compliance rules with 2M and 10M cutoffs.

  16. > “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.”

    This is a big quote

  17. Ballmer should be forced to sell.

    Kwahi needs to be penalised too. Fine him the full amount. Fuck him.

  18. This has become meta- commentary on the rot the billionaire class permeates into this country. Pablo put more than enough on the table round 1. Exposed the subtle walkbacks and true sycophants round 2. And now has made a case for the grand fraud that is contemporary sports journalism due to their financial entanglements.

  19. At what point does Pablo send over a bill to the law group the NBA hired? At this point in time, the NBA should have paid Pablo and moved on cuz this case is a slam dunk case. Sheesh.

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