Kawhi Leonard investigation expands as NBA examines two more financial arrangements

The NBA’s investigation into Kawhi Leonard and the Los Angeles Clippers reportedly reaches beyond the controversial Aspiration sponsorship deal that first triggered scrutiny nearly a year ago, with the uncertainty now putting Leonard’s planned trade to the Toronto Raptors on ice.
According to new reporting from The Athletic, the outside law firm conducting the inquiry has examined whether the Clippers paid expenses on Leonard’s behalf without receiving reimbursement. Investigators have also looked into whether Leonard held a previously undisclosed endorsement agreement with a second company.
“[The investigation] looked into whether the Clippers improperly covered expenses for Leonard but were not reimbursed for them, those sources said, wrote The Athletic. “And the firm has examined if Leonard had a previously unreported endorsement deal with another company, those sources said.”
Those two developments significantly broaden what was initially understood to be a narrow investigation centered on possible salary-cap circumvention.
The league hired Wachtell Lipton to determine whether the Clippers helped arrange Leonard’s lucrative agreement with Aspiration as a way to provide compensation outside his NBA contract. The environmental company agreed to pay Leonard $28 million, though he never appeared in a public advertising campaign before Aspiration’s financial collapse and eventual bankruptcy.
The Athletic reported that investigators are now following additional financial threads uncovered during the process. It remains unclear which expenses the Clippers allegedly covered, how much money was involved or what company was connected to the possible second endorsement deal.
No finding of wrongdoing has been announced.
The Clippers and owner Steve Ballmer have repeatedly denied using Aspiration to funnel money to Leonard. The organization maintains that it was among the investors and business partners defrauded by Aspiration co-founder Joe Sanberg, who pleaded guilty to federal wire fraud charges and was sentenced to prison.
“We did not funnel money to Kawhi Leonard through Aspiration,” the Clippers said in a recent statement, adding that the team expects the investigation to confirm it did not violate league rules.
The widening inquiry could shed light on why the case has continued into its 11th month despite NBA commissioner Adam Silver previously suggesting it was approaching a conclusion. Silver has said the league needs finality but also wants the outside investigators to complete a thorough review.
The delay has already complicated one of the offseason’s biggest potential moves.
Toronto paused its agreement to reacquire Leonard after the NBA informed the Raptors they would assume the risk of any discipline affecting him after the trade. The Raptors still intend to complete the deal but will wait until the investigation ends before taking on that uncertainty.
The NBA’s original question was whether Leonard’s Aspiration contract crossed the line between a legitimate endorsement and off-the-books compensation.
Now investigators appear to be asking something broader: whether the Aspiration arrangement was an isolated issue or part of a larger web of financial benefits surrounding the Clippers star.
Until the league answers that question, Leonard’s Toronto return—and the Clippers’ offseason—will remain frozen.