Bill Simmons Identifies 3 “Weird” Things About Kawhi Leonard Investigation That Make No Sense

Nearly a full year after the first explosive report dropped, the NBA’s investigation into Kawhi Leonard’s endorsement deals remains unresolved. Bill Simmons gave his take on three details that continue to make it unexplainable, even as the league and the Clippers differ over the probe’s findings.

On his podcast, Simmons stated the points that still leave him unsettled.

“The three actual things that still make me go, huh, with the Kawhi thing, this is now, we are now a year into this,” he said on the Ringer. “He never actually did the work for Aspiration but got paid. I’ve just never heard an adequate explanation for that. Why are you paying somebody to not do anything? Like not even like one Instagram tweet, nothing. That’s weird.”

Simmons then turned to Kawhi Leonard’s longtime adviser, Uncle Dennis Robertson.

“Uncle Dennis, by multiple accounts, just asking everybody for under-the-table shit in the summer of 2019 and multiple teams going on the record saying, oh yeah, that guy was fucking asking for ownership stakes. That was weird.”

The third thing that caught his attention was the Clippers’ recent decision to trade Leonard back to Toronto.

“Conspiracy Bill definitely like put a hat on and studied that one,” Simmons said, noting that the Raptors had just won a title with Leonard, could have been a serious Eastern Conference contender in 2020, and instead watched their Finals MVP walk away only to later re-acquire him as the investigation happened.

Those three observations arrive at a moment when the investigation itself has grown more controversial. The probe, which was launched after reports of a $28 million “no-show” deal with the now-bankrupt green-banking firm Aspiration (a company that had received a major investment from Clippers owner Steve Ballmer), has moved to include a second alleged endorsement arrangement and questions about team-facilitated introductions to sponsors.

A potential trade sending Kawhi Leonard back to the Raptors was put on hold earlier this summer because of the unresolved inquiry. The NBA and Clippers have disagreed over recent reporting on the probe’s status, with the league insisting the matter is still open and that final results will be released only when the independent review concludes.

The Three Details About the Kawhi Leonard Case Bill Simmons Still Can’t Agree

Simmons’ first point was the complete absence of any visible work done for the Aspiration payments. It remains a mystery, as no marketing campaigns, social-media posts, or public appearances have ever been tied to the deal in a way that matches the reported compensation.

His second observation revisited the 2019 free-agency period. Multiple teams privately described Robertson’s requests for ownership stakes and other off-the-books benefits as unusually aggressive. The league investigated those claims at the time and found no proof that any improper benefits were actually granted.

The third point was the Clippers shipping Kawhi Leonard to the one franchise with the clearest grievance. Toronto had every reason to remain wary after losing its championship centerpiece.

That the Raptors were willing to re-engage, and that the Clippers were willing to send him there while the investigation loomed, struck Simmons as the kind of development that invites closer scrutiny.

Whether any of these three points prove significant will depend on the final report.