Steve Ballmer's Ties To Aspiration Deepen With New $10 Million Investment

Steve Ballmer’s ties to Aspiration just got even murkier. According to a new report, the Clippers owner made a follow-up investment of nearly $10 million into the tree-planting firm at the center of the NBA’s investigation into Kawhi Leonard’s controversial endorsement deal, and it came just 18 months after his initial $50 million buy-in.

"Clippers owner Steve Ballmer invested almost $10 million into financial technology and sustainability services company Aspiration," reported The Athletic. "The previously unreported investment came 18 months after Ballmer’s $50 million investment in the firm now at the heart of an NBA investigation."

Ballmer’s additional $10 million investment raises even more questions about his knowledge and involvement. On one hand, Aspiration was falsifying financial documents, meaning they could have conned Ballmer and his financial team multiple times. Still, his multiple investments make it harder for Ballmer to feign ignorance now, especially since the last one came at a time when the company was doomed to fail.

"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," The Athletic's Mike Vorkunov added.

While we can’t assume guilt, the details are adding up against the Clippers. With each new piece of evidence that emerges, the franchise looks increasingly indefensible, and one has to wonder how it went over the NBA's head.

Kawhi's contract with Aspiration has been suspicious from the very start, including the sheer amount of money on the table ($28 million in cash and another $20 million in stock). The deal was much richer than Aspiration's other arrangements, and it included stipulations that allowed him to opt out of any marketing or promotional obligations.

That's not to mention Ballmer's routine involvement, as well as investments from his former roommate and minority Clippers owner, Dennis Wong. The Clippers are losing plausible deniability here, and it'll be up to them to explain this to the NBA. Unless they can prove that Apsiration acted independently from the team, it's reasonable to suspect that they used the company as a front to pay Kawhi.

Of course, the NBA's punishment will depend on what they can verifiably prove, but with a paper trail this long, it's unlikely that the Clippers will get off scot-free. Even with Aspiration in financial ruin, Ballmer paid an almost negligible amount that wasn't nearly enough to keep them going. It was, however, just enough to keep Kawhi's lucrative endorsement afloat.

Overall, it's just a bad look and makes the situation stink even more than it already did. Ballmer's involvement with Aspiration can no longer be denied, and he can't claim he was being scammed when he kept putting money into the clearly failing company.

At this point, the Clippers’ defense is hanging by a thread. The deeper people dig, the more connections surface between Ballmer, Aspiration, and Leonard’s contract. If the NBA wants to send a message about cap circumvention, Los Angeles may end up being the perfect example of what happens when a franchise gets too comfortable skirting the rules.