Report: Steve Ballmer made a second, $10 million investment into failing company that endorsed Leonard

Clippers’ owner Steve Ballmer’s defense in the Kawhi Leonard salary cap circumvention and “no show” endorsement scandal has been “plausible deniability.” Ballmer said he was “duped” like other investors when he put $50 million into the green bank company Aspiration (a company that had become a $300 million Clippers team sponsor back in 2021, but now is bankrupt with its CEO pleading guilty to fraud). Ballmer noted that the Clippers ended their team sponsor relationship with Aspiration after it defaulted on its obligations, and said both he and the team knew nothing about Leonard’s $48 million endorsement deal with Aspiration ($28 million in cash, the rest in stock) other than that it existed. Ballmer vehemently denied the charge that the Clippers used Leonard’s Aspiration endorsement to circumvent the NBA salary cap.

That argument is becoming increasingly difficult to believe.

After a detailed initial report came a second one from the Pablo Torre Finds Out podcast (which broke the story initially) that Clippers minority owner Dennis Wong invested $2 million into Aspiration late in 2022 — when the company was failing and struggling to make payroll — and a week later Leonard got a delayed $1.75 million quarterly endorsement check.

Now comes a report that Ballmer made a second, $10 million investment in Aspiration in March, 2023, despite it being clear at that point the company was failing and headed toward bankruptcy. The report comes from Mike Vorkunov at The Athletic.

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…

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.

What is not known is when the payments on Leonard’s endorsement stopped. He is a creditor in Aspiration’s bankruptcy, seeking $7 million he is still owed.

Ballmer and the Clippers have not commented on the latest allegations, but their defense is likely the same: Ballmer was making a personal investment (and not a big one for Ballmer, who Forbes estimates is worth $153 billion), hoping to prop up the company and recoup his original investment, that this had nothing to do with Leonard.

This latest report is another wave in the tsunami of evidence that the Clippers used Aspiration to funnel extra money to Leonard outside his standard contract — maybe it’s all circumstantial evidence, at least what we see publicly, but it’s not hard to connect these dots. It’s short, straight lines between these dots.

NBA Commissioner Adam Silver said Wednesday that the burden of proof is on the league — which has hired a law firm to do its investigation as a third, neutral party — and that he “would be reluctant to act if there was sort of a mere appearance of impropriety.”

It feels like more than an appearance now, the buzz in league circles is that many owners feel the same way, which means Silver is going to have to bring the hammer down on the Clippers (likely taking away future first-round draft picks, fining the Clippers up to $7.5 million, suspending team executives, and he could potentially void Leonard’s contract, although that last one is unlikely).

The NBA’s formal investigation is ongoing and likely will drag out for a while.