Steve Ballmer once promised the Clippers would be “hardcore.” Eleven years later, the franchise remains hardcore, just not in the way he had imagined. Instead of celebrating championships, the team is trapped in secrecy, lawsuits, and a fresh NBA investigation that circles back to the one question insiders can’t avoid: is it finally time to get out of the Kawhi Leonard business? That’s not just speculation. In fact, it’s a sentiment whispered from within Ballmer’s own orbit.
“At some point, Steve has to get out of the Kawhi Leonard business,” one former staffer admitted, as reported by Baxter Holmes speaking on NBA Today. And while the Clippers remain optimistic that a healthy Leonard can still anchor a contender, the growing pile of missed games, legal scrutiny, and broken promises threatens to be too large to ignore.
The Clippers signed Leonard in 2019 and bent their entire identity around him. They gave up Shai Gilgeous-Alexander, a then-rising rookie and recent champion, along with five first-round picks and two swaps for Paul George, to satisfy Leonard’s demands. They allowed him helicopter commutes from San Diego, freedom to skip media obligations, and marketing control unlike anything in franchise history. And they even fired broadcaster Bruce Bowen for on-air criticism.
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Leonard wanted a star-friendly ecosystem, and Ballmer, desperate to shed the Donald Sterling era and finally bring a banner to Inglewood, delivered. But the costs were overwhelming. In six seasons, the Clippers have just three playoff series wins and zero Finals appearances. Leonard has suited up for only 58% of possible games, his body breaking down at the worst possible times. And behind the scenes? A conveyor belt of investigations.
The NBA has fined the team over his health disclosures, probed tampering allegations, and is now examining whether a $28 million sponsorship tied to Ballmer’s personal investment amounted to salary-cap circumvention. “This last investigation is different,” a former Clippers staffer warned. “This one directly calls into question Steve Ballmer’s character.”
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And yet Leonard remains under contract for two more years at $50 million annually. He’ll be 36 when that deal expires, with more surgical scars than playoff banners to show for his LA stay. As Holmes added, “People I talked to do said they expect him to play through this current contract. Beyond that, no one’s quite sure.” Ballmer’s boldest bet was supposed to liberate the Clippers from irrelevance. Instead, it’s become a gilded cage.
The Kawhi Leonard gamble that became a cage
The trade that gave Oklahoma City Shai Gilgeous-Alexander has aged into one of the most lopsided deals in league history. The Thunder are now riding SGA’s superstardom into perennial contention. Meanwhile, the Clippers? They’re betting on the health of a player whose relationship with truth and transparency has been clouded at best.
If Adam Silver doesn’t step in decisively, what’s to stop future owners from engineering similar loopholes? The commissioner admitted the $28 million Aspiration deal tied to Kawhi Leonard triggered questions serious enough for the league to consider hiring outside counsel.
He acknowledged the NBA’s vetting process may not dig deeply enough into every sponsorship and warned that rules might have to be rewritten to ensure competitive balance. “My responsibility ultimately is the integrity of this league,” Silver said, framing the issue less as a Clippers scandal and more as a systemic test of how far private business can bleed into basketball. The potential penalties are no slap on the wrist.
Under Article XIII of the CBA, Silver could fine the Clippers millions, strip future draft picks, or suspend executives. In the harshest scenario, he could even void Leonard’s contract entirely, a punishment that might punish LA on paper but also scramble the free-agent market mid-season. That’s the paradox Silver has to solve: hit hard enough to protect the league’s credibility, without detonating its competitive map. Coming back to Leonard, though, Leonard’s quiet knee procedure also blindsided Team USA, who expected him to be a defensive anchor in Paris.
Months later, a lawsuit from former Clippers strength coach Randy Shelton alleged tampering, undisclosed injuries, and even financial threats from Leonard’s camp. While the team dismissed most claims as extortion, they didn’t deny one core reality: Kawhi’s world has always operated in shadows. And the problem isn’t just optics here.
It’s culture. Multiple ex-staffers described a franchise ruled by fear. Fear of upsetting Leonard, fear of slipping the wrong word into a press release, and most importantly, the fear of losing the very star they mortgaged their future for. Doc Rivers once joked to reporters, “I’m scared to answer” when asked about Leonard’s health. That was 2019. Five years later, the punchline reads more like prophecy. So where does that leave Ballmer? A billionaire who once declared the Clippers would win “many, many more Larrys” now faces the prospect of leaving without even one.
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The irony is brutal. In trying to prove the Clippers could finally handle a superstar, Ballmer built a system that allowed Leonard’s camp to run the show. And the return on investment? A “f—— disaster,” as one rival GM flatly called it. For now, the plan is to ride it out. Leonard’s deal locks him in, and the Clippers, having doubled down with aging stars like Harden, Beal, and Chris Paul, aren’t exactly set up to pivot.
The anonymous source’s advice might sound harsh, but it cuts to the truth that at some point, Ballmer may have to admit that the hardcore path isn’t clinging to Kawhi, but rather cutting him loose.