Kawhi Leonard already has a new home after the Los Angeles Clippers traded him back to his former team, the Toronto Raptors, this offseason. However, with the NBA’s investigation into Leonard and the Clippers still ongoing, the trade remains on hold.
Meanwhile, Bill Simmons has highlighted three major issues surrounding the investigation into Kawhi Leonard, Steve Ballmer, and the Los Angeles Clippers over alleged salary-cap circumvention.
Bill Simmons Uncovers 3 Red Flags in Kawhi Leonard Investigation
Leonard’s investigation began after Pablo Torre reported on his alleged endorsement arrangement with Aspirations. The investigation remains clouded in uncertainty, with its potential consequences and broader impact still unclear.
On his podcast, Simmons first questioned why a corporate entity would agree to pay a star athlete millions of dollars despite seemingly receiving little or no active work from the player in return.
“The three actual things that still make me go with the quiet thing, this is now we’re now a year into this,” Simmons said.
“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.”
The three things that still make no sense to @BillSimmons about the Kawhi-Aspiration situation pic.twitter.com/HQxjYVhATo
— The Ringer (@ringer) August 19, 2026
Simmons then turned his attention to Kawhi’s 2019 free agency, specifically focusing on the actions of his uncle and longtime advisor, Dennis Robertson, who contacted multiple teams during the 7-time All-Star’s free agency process while seeking benefits not permitted under the NBA’s salary cap rules.
Simmons pointed to multiple NBA executives who had reportedly mentioned discussing the unusual requests allegedly made during Leonard’s free agency.
The third issue the analyst raised was the Clippers’ decision to trade Leonard back to Toronto this offseason.
Meanwhile, ESPN reported that the NBA has found no evidence that Clippers owner Steve Ballmer funneled money through team sponsors to pay Leonard in an effort to circumvent the salary cap.
Furthermore, the league’s attention has reportedly shifted instead to whether the Clippers’ introduction of Leonard to team sponsors violated NBA salary-cap regulations.
However, just hours after the report surfaced, NBA spokesperson Mike Bass issued a strong statement directly disputing ESPN’s characterization of the league’s findings.
NBA Commissioner Adam Silver previously indicated that he wanted the investigation resolved before the beginning of the 2026–27 regular season. With several major questions still surrounding Leonard, Ballmer, and the Clippers, it will be fascinating to see what conclusions the league ultimately reaches.
