Bill Simmons has kept his criticism of the Kawhi Leonard era blunt and public, and he recently doubled down on a claim that has been circulating across podcasts and social feeds. On The Bill Simmons show, he warned that league insiders are frustrated and that questionable deals are more common than fans think, “Some of the stories have talked about how furious other teams are… Get the f–k out of here. Half the league does this. I wish I could say 10% of the stuff I’ve heard… Everything you think is happening is happening. Just period”. That line frames why the Leonard story is now talked about as an institutional problem.

The cost of acquiring Kawhi is easier to chart than it is to defend. In 2019, the Clippers traded Shai Gilgeous-Alexander, Danilo Gallinari, and seven first-round selections and swaps to land Paul George, and then signed Leonard, a move that left the franchise without first-round picks for several years. During Kawhi’s tenure, the Clippers have managed only three playoff series wins. Now, with the $28 million Aspiration controversy clouding his stay even more, Simmons has escalated his criticism to a historic level, delivering a scorching take on the entire transaction.

Simmons said on his podcast, “This Kawhi, the entire thing of going into business with this dude, all the stuff that cost them, all the players and the draft picks, plus this scandal. It has to be the most damaging transaction in the history of the league”. He doubled down, adding, “I don’t even think you could compare it to anything. It’s already retroactively one of the worst trades of all time”. 

The podcast guest argued about the Luka trade comparison- quoting “It’s not worse than Luka“. To which Simmons said, “They end up with Cooper Flagg!” Simmons believes that the fact that the Doncic trade eventually led to the Mavericks snagging the No. 1 pick at least in part made up for their loss. In Kawhi’s case however, the script of damage runs deeper.

“All right. Just forget all the dumb reasons behind the trade. Would you trade Anthony Davis and Cooper Flag for Luka?”. The guest replied with “No,  f–k no. How strongly can I put it? F–k No!!”.

The numbers make Simmons’s point hard to ignore. To land Kawhi the Clippers agreed to acquire Paul George in a deal that sent Shai Gilgeous Alexander, Danilo Gallinari and five first round picks plus two pick swaps away from the franchise. Since then, Shai, now an NBA MVP, has helped his new team reach the championship while the Clippers managed just three playoff series wins with Leonard available roughly 58 percent of the time.

Further, Kawhi’s tenure with the Clippers has been botched with injuries as he has missed 132 regular-season games that has come alongside crucial absences during postseason runs. Further, the Clippers have gone all in on the player whose individual numbers undoubtedly remain consistent. They signed him on a three-year $176 million extension in 2021 in a move that has current financial implications as well, considering they are firmly over the first apron.

Add to that the Aspiration saga which is set to have historic consequences for the entire franchise and maybe even the league, Simmons’ point gets a lot of weight. Clippers officials have pushed back publicly, framing Aspiration as a sustainability partner and saying their arena commitments required buying carbon offsets. Owner Steve Ballmer has told audiences he welcomes scrutiny and wants the facts to come out, a posture intended to separate corporate investments from player deals.

“I welcome the investigation,” Ballmer said in public remarks while also insisting the team acted within the rules. That stance now leads into a quieter fight behind the scenes over how the league will rule and whether the Clippers can repair both the roster hole and a reputation that has taken a serious hit.

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When the Clippers issued their formal response they emphasized sustainability work and arena commitments as the reason for large payments to Aspiration, arguing the transactions were tied to carbon offsets rather than player compensation. In a statement the team explained that the Intuit Dome was designed around carbon neutrality and that payments to Aspiration were part of those built in development agreements. “Steve and his family are focused on sustainability, which is why Intuit Dome was designed to be a carbon neutral building from its inception and to achieve LEED Zero status over time,” the statement read, a line meant to reframe the narrative away from impropriety.

That explanation still sits beside a detailed timeline published by investigative reporters that shows the Clippers and related parties funneled roughly $118 million to Aspiration across 18 months, including $56 million in carbon credit payments in the spring of 2022. The same reporting notes a near term $1.75 million payment to Leonard and a private $1.99 million investment by a Clippers minority owner shortly before that payment cleared. Aspiration later collapsed and its co founder pleaded guilty to fraud, facts that have complicated the club’s defense and fed league interest in forensic accounting of those cash flows.

Commissioner Adam Silver has said the league will take its time and look for hard evidence rather than appearances, language that sets a high bar for sanctions while signaling seriousness. “If I said I never heard of it, I meant in the context of the accusations here,” Silver recently told reporters, a line that underscores how quickly public narratives can shift as new documents surface. The league has engaged outside counsel for the probe and rival executives are watching closely because any ruling will reshape how teams manage sponsor relationships and owner investments going forward.

The stakes are real because the penalties can be dramatic and precedent exists for harsh action when rules are broken, a dynamic that helps explain the heat behind Simmons’s claim. If the league finds circumvention it can impose fines, strip draft picks and void transactions, outcomes that would reshape the Clippers for years. For now the investigation continues, the official statements stand on record and Simmons’s verdict has helped define public debate about whether a single signing can carry consequences that last well beyond a player’s minutes on the floor.