What began as a $28 million “no-show” endorsement deal between Kawhi Leonard and the now-bankrupt tree-planting startup Aspiration Inc. has ballooned into something far more complex, and potentially far more damning.
According to Boston Sports Journal, Leonard’s total compensation from Aspiration may have reached a staggering $48 million, nearly matching the $50 million investment made by Clippers owner Steve Ballmer into the same company.
Initial reports, including those from Pablo Torre, revealed that Leonard signed a $28 million endorsement deal in 2022 through his LLC, KL2 Aspire. The agreement required no public appearances, no promotional content, and no social media posts. In fact, Leonard never publicly mentioned Aspiration at all.
Now, new findings suggest Leonard also received $20 million in company stock, bringing his total compensation to $48 million. That stock, reportedly paid out from co-founder Joe Sanberg’s personal holdings, is now worthless following Aspiration’s bankruptcy. But the cash payments remain, and Leonard is still owed $7 million, making his LLC one of the company’s top creditors.
Ballmer’s $50 million investment in Aspiration came at a price of $11 per share, oddly higher than the $10 per share paid by institutional investor Oak Hill Capital. For someone of Ballmer’s stature and negotiating power, paying a premium is unusual. The timing is even more suspect: Ballmer’s investment and Aspiration’s jersey patch sponsorship with the Clippers were finalized just before Leonard signed his deal.
The proximity of these transactions has led to speculation that Ballmer’s investment may have indirectly funded Leonard’s compensation, raising serious questions about salary cap circumvention.
This isn’t the first time the Clippers have been accused of bending the rules. In 2015, the team was fined $250,000 for offering unauthorized endorsements to DeAndre Jordan during free agency negotiations. That incident, while smaller in scale, now looks like a precursor to a more sophisticated strategy.
The NBA has launched a formal investigation into the Leonard-Aspiration arrangement. If the league finds evidence of cap circumvention, the Clippers could face severe penalties, including fines, loss of draft picks, and voided contracts.
Leonard’s LLC, KL2 Aspire, was formed just months before the endorsement deal and shortly after he signed a four-year, $176 million extension with the Clippers. The name itself, KL2 Aspire, appears to be a direct nod to Leonard’s initials, jersey number, and the company.
While the Clippers continue to deny any wrongdoing, the mounting evidence suggests that this was more than just a generous endorsement deal. It may have been a carefully orchestrated financial maneuver designed to reward a franchise cornerstone without triggering salary cap penalties.
