Report: Steve Ballmer invested several millions more in Aspiration in 2023

Things are quickly going from bad to worse for the LA Clippers and their plausible deniability.

Clippers owner Steve Ballmer is alleged to have invested an additional sum of nearly $10 million in Aspiration, a now-bankrupt technology and sustainability services company that once served as a Clippers team sponsor, in 2023. Mike Vorkunov of The Athletic made the claim in a report released on Friday night, citing legal filings reviewed by The Athletic that were corroborated by a former Aspiration executive.

Details of The Athletic's report on LA Clippers owner Steve Ballmer

Ballmer allegedly made an initial investment of $50 million in the company in 2021, which was revealed by sports journalist Pablo Torre earlier this month. Seven months after Ballmer’s 2021 investment, Aspiration then reportedly signed Leonard to a $28 million endorsement deal in which he allegedly did nothing for them in return. Ballmer and the Clippers are accused of having actually used Aspiration to funnel under-the-table money to Leonard in order to circumvent the NBA salary cap.

Vorkunov reports that Ballmer then made an additional investment in Aspiration nearly 18 months later in 2023. The investment was allegedly part of a fundraising round (made up almost exclusively of existing Aspiration investors) that sought to raise $75 million in fresh cash amid the company’s financial struggles at the time.

You can read Vorkunov’s full report on the situation here.

Earlier this week, Clippers minority owner and alternate governor Dennis Wong, who used to be Ballmer’s college roommate, was revealed to have allegedly invested his own sum of roughly $2 million into Aspiration in late 2022 after the company was supposedly having difficulties paying Leonard pursuant to his endorsement deal. Leonard was then allegedly paid nine days after Wong’s reported investment (read the full details here).

As for Ballmer’s 2023 investment in Aspiration, that would seemingly run counter to his recent public statements about the scandal. Ballmer claimed in an interview with ESPN last week that he was “conned” by Aspiration (yet he now allegedly had a second significant investment in the company some 18 months after his initial investment).

The NBA has launched an official investigation into the Clippers over the matter, hiring New York-based law firm Wachtell, Lipton, Rosen & Katz to run point. Rival executives reportedly want the Clippers to face a harsh penalty for their alleged misdeeds, and now it is seemingly getting much tougher for the Clippers to plead ignorance here.