Stephen A. Smith Throws Kawhi Leonard’s Family Member Under The Bus After Illegal Demands Resurface

Kawhi Leonard has been one of the quietest superstars in the league, but his name has been loud in headlines all week. A bombshell report on his business ties and the Clippers sparked heavy debate, and as usual, Stephen A. Smith did not hold back. Smith has often gone after players who frustrate him, and Kawhi is near the top of that list. Just earlier this year, he said he was “waiting for Kawhi to get injured.” This latest controversy gave him even more material.

The NBA has already looked into aspects of that 2019 free agency before, and as one high profile commentator pointed out this week, “The NBA completed that investigation into Robertson, also known as Uncle Dennis, and found no evidence the Clippers granted illegal benefits to Landon while pursuing him in free agency”. That lingering history helps explain why new allegations moved fast.

The story that resurfaced involves Kawhi Leonard’s uncle and adviser Dennis Robertson and reports that extraordinary perks were requested during the free agent sweepstakes that summer. Multiple outlets have reported that teams were asked for benefits well outside normal endorsement talks, and sources say some suitors pushed back. Lakers owner Jeanie Buss reportedly told Robertson those types of asks were illegal and would not be considered. Those old tensions are the backdrop for fresh reporting that claims a now bankrupt outside company paid Kawhi millions in a way that may have skirted the salary cap.

Then Stephen A. spoke up and made the family angle a central talking point on his show, pushing the conversation from boardroom leaks into hot TV takes. In a clip posted to YouTube, he framed the situation around Robertson’s role and why the allegations demand scrutiny, saying, “Let me tell you something that I know about Uncle Dennis. I’m certainly not going to accuse him of something illegal, but anything legal and within bounds that falls under the category of a perk, if anybody’s going to ask for all of them for Kawhi Leonard, it’s him.”

Stephen A. also stressed that the allegations are serious, saying “it does warrant an investigation”, which is notable because his rhetoric tends to amplify public pressure on league offices and team executives.

Outside of television, social posts and reporting added sharp details that bring the 2019 free agency back into focus. A popular X post put a long Athletic passage back into circulation and reminded people that Robertson allegedly demanded ownership stakes, a private plane, a house, and guaranteed off court endorsement money when courting teams. The post argued that some people did not believe early whispers about Kawhi’s Lakers talks and that Robertson was pushing hard. Another brief social update relayed that Kawhi Leonard reportedly asked Toronto’s owner to line up an extra 15 million in endorsements as part of his decision making. Those social signals show how quickly old sourcing and new documents can reconnect in the public mind.

The bigger reporting that set this off claims a now bankrupt firm named Aspiration sent 28 million dollars to a company tied to Kawhi, and that parts of the contract allowed payment without active promotion so long as Kawhi remained with the Clippers. Aspiration later filed for bankruptcy and prosecutors say the company engaged in fraud, and one former employee told investigators the payment looked like a way to circumvent the salary cap.

The Clippers and owner Steve Ballmer have denied wrongdoing in a public statement, writing “Neither Mr. Ballmer nor the Clippers circumvented the salary cap or engaged in any misconduct related to Aspiration. Any contrary assertion is provably false.” Meanwhile the league confirmed that it has opened a review and said, “We are aware of this morning’s media report regarding the LA Clippers and are commencing an investigation.” Those two official lines mean this could move from headlines to formal process very soon.

Right now, the debate sits at the intersection of public perception and formal rules, and that is why Stephen A. aimed his fire at Robertson in a way that put family and business behavior in the same frame. If the NBA finds evidence that the deal was structured to sidestep pay rules, the penalties can be sharp and long lasting, and the public rhetoric will matter when commissioners and lawyers decide how to proceed. For fans, the immediate takeaway is that this is more than a gossip item; it is an allegation with legal and competitive implications that ties back to decisions made in the heat of a high stakes free agency.

A franchise under scrutiny again

The Clippers have history on this front because of a prior episode in 2015 when the organization was fined over an improvised endorsement pitch tied to the DeAndre Jordan saga, a reminder that the league has punished teams for trying to package off court perks into player recruitment. That 2015 episode resulted in a 250 thousand dollar fine and put the franchise on notice that direct facilitation of specific third party deals crosses a line, which is why comparisons to the current allegations keep surfacing in reporting and analysis.

The collective bargaining agreement contains clear anti circumvention rules designed to keep compensation transparent and fair, and penalties are serious. Under Article XIII the league can impose fines running into millions, strip draft picks, void contracts or suspend executives when it finds deliberate attempts to bypass the cap, and the memorable Joe Smith case shows how brutal the fallout can be when the NBA deems a scheme to be real. Those structural safeguards explain why journalists and front office people view the new reporting as potentially explosive rather than merely embarrassing.

The specific Aspiration reporting, the employee testimony and the trail of corporate documents create a paper record that investigators can follow, and that is why the NBA said it is commencing an investigation. One former Aspiration staffer described being told to avoid questions because the setup was intended to “circumvent the salary cap. LOL,” a line that underlines why league officials now need to sort legal fact from loud commentary. As the probe proceeds the Clippers will press denials and legal teams will sort contract language, but Stephen A. and others have already ensured the family angle and the old 2019 controversy will not disappear while the league looks for answers.