It has been nearly a year now since the NBA launched an investigation into the Los Angeles Clippers and Kawhi Leonard over cap circumvention, and there’s still no resolution. This has been quite a bizarre saga, and The Ringer’s Bill Simmons is still scratching his head over some aspects of it. Simmons pointed out three things that make no sense to him about this situation on The Bill Simmons Podcast.
“The three actual things that still make me go, huh, with the Kawhi thing,” Simmons began. “We are now a year into this. 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.
“Uncle Dennis [Robertson] by multiple accounts, just asking everybody for under-the-table s*** in the summer of 2019,” Simmons stated. “And multiple teams going on the record saying, ‘Oh yeah, that guy was f***ing asking for ownership stakes.’ That was weird. And then the third one was the Clippers trading Kawhi to Toronto.
“Put this way, Conspiracy Bill definitely like put a hat on and studied that one,” Simmons continued. “‘Cause it was like, ‘All right, Toronto is the one team with a real, real, real reason to be aggrieved, right?’ They just won the title… He didn’t want to play for the Lakers as it comes out. They could have brought this guy back. They were really good in 2020.
“They probably would have represented the East and played the Lakers in the Finals,” Simmons added. “And all that got pulled away, and they have the biggest reason to be pissed. And instead they trade him there, and now it’s like, ‘All right, I guess we have Kawhi now. It’s fine.’ Those are the three things that caught my eye.”
Of course, all of this began with Aspiration, a now-defunct environmental company. It was alleged back in September 2025 that the Clippers had circumvented the salary cap through Aspiration. The company had given Leonard a $28 million endorsement deal, but as Simmons pointed out, he wasn’t required to do anything for them. It was a “no-show” job.
To go with this, Aspiration also reportedly gave Leonard $20 million in stock. That gets us to $48 million in total, and Clippers owner Steve Ballmer had interestingly invested $50 million in the company. Ballmer, Leonard, and the Clippers have firmly denied any wrongdoing, but this is quite puzzling.
We next get to Dennis Robertson, Leonard’s uncle and business advisor. Robertson reportedly sought perks from the Los Angeles Lakers in free agency in 2019 that would have violated the NBA’s Collective Bargaining Agreement. That same offseason, he is also said to have asked the Toronto Raptors for a stake in the NHL’s Toronto Maple Leafs. The NBA investigated this, but didn’t find anything concrete.
Leonard would end up leaving the Raptors in that 2019 offseason for the Clippers. It should be pointed out, though, that this Aspiration deal was signed in 2022. It’s unlikely that it had anything to do with Leonard joining the Clippers.
Now, seven years after leaving the Raptors, Leonard looked to be on his way back in 2026. The Clippers agreed to send the seven-time All-Star to Toronto for Brandon Ingram, Gradey Dick, unprotected first-round picks in 2031 and 2033, a 2027 first-round pick swap and two second-round picks.
The Raptors would put the Leonard trade on hold, though, once the NBA informed them that they would assume any risk of any penalties the 35-year-old might incur from the investigation. Unsurprisingly, they were not willing.
Not long after that, it was reported that Leonard had another multimillion-dollar deal with Daktronics, the company that manufactured the Intuit Dome’s Halo video screen. To say there was now a lot of smoke would be an understatement.
This saga appeared to have concluded when ESPN reported that the NBA had found no evidence that Ballmer funnelled money through team sponsors to Leonard. The league dismissed the report, however, stating it had numerous and significant inaccuracies. The NBA says the investigation is still not over, so we’ll just have to wait and watch.
