ESPN Insider Reveals 2 Fishy Details About Kawhi Leonard Deal After Steve Ballmer’s Confession

Kawhi Leonard has been a quiet superstar for years, but he is suddenly loud in the headlines again because of a business story that ties together a bankrupt company, an owner, and questions about how players get paid. The background is public and simple to follow. Pablo Torre published a deep investigation that says a now-defunct firm called Aspiration paid roughly twenty-eight million dollars to a company tied to Leonard. That claim reached the NBA and the Clippers almost immediately. That sequence of reporting is why this is no longer just rumor mill chatter.

The last six months made this a lightning rod. The league had already looked into aspects of Kawhi Leonard’s 2019 free agency. And the record shows the NBA completed that probe and found no evidence that the Clippers granted illegal benefits back then. Commentators have not let the topic die. Stephen A. Smith pushed the family angle hard on national television and questioned the involvement of Dennis Leonard, Kawhi’s uncle.

And now, another ESPN insider raised two very specific red flags that change how the puzzle looks. Brian Windhorst didn’t shy away on his podcast. ‘Brian Windhorst and the Hoop Collective’ took to Spotify and posted a podcast episode that dug deep into the suspicious details of this alleged deal. Highlighting two particularly concerning aspects that stuck out to him, he said, “So two things to me that stick out here as fishy. One, that they do this deal and it’s never announced. The entire concept of it was to be marketing. And it would be one thing if the company, like, signed a bunch of people and, like, had a, you know, 2025 marketing plan where they were going to roll out all these celebrities. But they had other celebrities that they signed that, you know, were using as marketers. Okay, so that one is that they sign them to a deal and then never announce it. Never use them and never announce it”, Windhorst explained.

The odd silence around an arrangement supposedly designed for promotion definitely rings a bell, considering NBA stars routinely get involved in such marketing stunts.

Windhorst’s second major concern involved the financial terms themselves. “Okay, the second thing is four years and $28 million. And there’s been some other reporting today that it was worth more. But I’m just going to look at what Pablo reported was in the- he had leaked to him the actual document. That, in talking to some agents, is not a market figure for this type of endorsement. As you said, McMahon, this is the type of endorsement a superstar player would get with a shoe company. Even if you didn’t, you know, even if you had your own shoe, you might not even get $7 million a year”, he noted.

The veteran analyst emphasized that $7 million annually typically represents what “a superstar player would get with a shoe company” for actual endorsement work. Not for a deal that allegedly required evidently minimal effort from Leonard.

Windhorst’s two points line up with other reporting. Torre found documents that show the agreement paid Leonard roughly twenty eight million dollars over four years to a company called KL2 Aspire LLC and that parts of the contract allowed payment with minimal promotional work as long as Leonard stayed with the Clippers. Former Aspiration employees told Torre they were told not to ask questions and that Leonard’s contract looked like a no show job.

The Clippers pushed back with an official statement, saying “Neither Mr. Ballmer nor the Clippers circumvented the salary cap or engaged in any misconduct related to Aspiration. Any contrary assertion is provably false”. At the same time prosecutors have charged Aspiration’s co founder with fraud as he was accused of having cheated investors and lenders out of $248m just last month. The company has since also filed for bankruptcy after it was revealed “financial statements were inaccurate and reflected much higher revenue than the company in fact received,” per Al Jazeera.

These concerns gain more weight when considering the broader context. Aspiration had a very public $300 million sponsorship deal with the Clippers that included jersey patch visibility, making the silence around Leonard’s involvement even stranger. Meanwhile, other celebrities like Leonardo DiCaprio and Robert Downey Jr. actively promoted the company, in stark contrast to Leonard’s complete absence from their marketing efforts.

This all matters because of the league’s strict rules on compensation and past precedent. The NBA confirmed it opened a review and an NBA spokesman said “We are aware of this morning’s media report regarding the LA Clippers and are commencing an investigation”. That formal step moves the story from hot talk to process and makes the next weeks critical. While commentators and reporters parse documents and motives, league lawyers will be hunting for hard evidence tying payments to competitive advantage. The public debate is loud, but the legal outcome depends entirely on paper trails.

Ballmer’s curious distance from the situation

Clippers owner Steve Ballmer has since spoken to media and insisted he had no direct role in any alleged side deals, while also explaining how he met Aspiration’s founders. Ballmer told ESPN “I have not spoken to Leonard about the allegations, no. It’s really his business with Aspiration, so I wouldn’t ask about it, no”. He claimed the Clippers simply made introductions between a sponsor and players while believing they were not crossing rules. In that same interview he argued the bankrolled investment came before any player deal and stressed he did not control Aspiration’s operations.

Ballmer also framed himself as a victim of fraud rather than an architect of a cap dodge. He told interviewers “They later asked to be introduced to Kawhi. According to the rules, we can connect our sponsors with our athletes, but we cannot be involved”. Later adding-  “These are individuals who committed fraud. They deceived me”. Prosecutors have already tied Aspiration’s internal books to a larger fraud scheme. And a co-founder pleaded guilty to charges that allege massive investor deception. Ballmer’s account shifts the focus toward Aspiration’s misconduct rather than automatic collusion between owner and player.

Even with Ballmer’s denial and claims of being duped, he also emphasized cooperation and reputational stakes for the franchise. In interviews he said “We’ve really emphasized doing things the right way. Doing things the right way, whether it’s the way we treat our fans, our players, our staff, the rules, do things the right way. And I want our fans to really understand that they’ve aligned themselves, that they support an organization that does things the right way. I mean, that’s fundamental. We welcome the league investigation. We have nothing to hide”. That line is an appeal to transparency. But it also signals the Clippers expect the inquiry to determine whether their actions were compliant or exposed to legal risk.

Where this goes next is procedural and potentially precedent setting. Article XIII of the collective bargaining agreement spells out severe penalties for circumvention including fines loss of draft assets and other sanctions. Past cases show punishments can be steep if the league finds a pattern of hidden compensation used to skirt cap limits. Between Windhorst’s two fishy details Ballmer’s public defense and Torre’s document based reporting the NBA has plenty to examine. For now, the investigation will sort the public narrative from the legal record and the answers will determine whether this ends as a messy media story or a landmark enforcement case.