The Clippers’ Kawhi Leonard era has been messy for a while, and the Aspiration saga has only made things worse. Since joining Los Angeles in 2019, Leonard has missed 206 of 472 regular-season contests across his tenure, a simple fact that has repeatedly shaped roster choices and playoff outcomes. Owner Steve Ballmer’s billion-dollar ambitions collided with repeated availability questions. Now, with the Clippers being investigated for potential cap circumvention, things are looking set to get worse.
Inside reporting paints a franchise that has shifted its approach after years of accommodation and controversy, and multiple insiders told Baxter Holmes the Clippers’ focus has changed. “They’re done building around [Kawhi],” one former staffer told Holmes, a blunt assessment that signals a pivot away from structuring the team to protect one high-profile but often absent star. However, with the latest saga potential set to lead to eventual suspensions and even potential pick-related measures, the relationship appears to be heading towards total breakdown.
Baxter Holmes recently summed up the situation while writing for ESPN. “The Clippers tried to keep Kawhi Leonard happy & healthy. What followed was fear, secrecy, lawsuits, fines & investigations — now leading to owner Steve Ballmer. “At some point,” an ex-staffer says, “Steve has got to get out of the Kawhi business,” he posted on X. Per the report, sources at the franchise suggest that it is only a matter of time before the Clippers part ways with Kawhi, simply because of the way their long-term trust has been repaid. Holmes’s deep piece lays out the Aspiration timeline, minority owner Dennis Wong’s $1.99 million investment days before a delayed $1.75 million payment to Leonard, and the broader legal and league scrutiny that has forced the team into damage control.
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The Aspiration flow and the role of Kawhi’s inner circle are central to why fans feel the franchise is cutting ties. Holmes reports that Kawhi remains under contract through 2026 27 yet the organization is already planning for life without him, positioning cap flexibility for the 2026 and 2027 free agent classes and noting that the Clippers do not control several future draft assets because of prior trades. Coverage also revisits the extraordinary demands made by Dennis Robertson during the 2019 free agency cycle, from requests for ownership stakes to private travel and special media rules, items that helped reshape how the Clippers operated around Kawhi and now complicate their public defense.
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For supporters and critics alike the underlying measures are tangible. League sources and front office executives told Holmes they expect Leonard to finish his deal, but the franchise’s internal signals are clear: build elsewhere and preserve future maneuverability. That organizational shift and the ongoing Wachtell Lipton led investigation into Aspiration put Ballmer and Clippers leadership in a position where public patience is limited. Of course, that is also dependent on what the NBA finds as part of its investigation.
Pablo Torre’s claims suggests that there is paper trail linking Dennis Wong to questionable investment in Aspiration just days before a $1.75 million payment was made to Leonard despite the company laying off 20% of its employees the same day. Any actual evidence that the NBA finds linking the Clippers to cap circumvention may mean that the damage may already have been done. While the Clippers may finally be willing to part ways with Leonard, it may already be too late.
Immediate and fierce fan reaction to this unfolding drama
Many fans zeroed in on the Uncle Dennis role and used it to explain why Kawhi could be vulnerable by association, noting that Robertson’s demands in 2019 went well beyond normal representation. “If ‘Uncle Dennis’ is the reason behind this then Kawhi is cooked himself too lol,” one post read, and that reaction leans on documented facts. Reporting shows Robertson pushed for franchise equity, guaranteed off court deals, private travel perks and lenient media obligations, concessions the Clippers accepted in part and that now tie the team to complicated endorsement deals and to the Aspiration payments that drew league scrutiny.
Other users expressed blunt relief at the possibility of a reset, citing Leonard’s limited court time and perceived special treatment as the root of frustration. “Please let it happen. I’m done with Kawhi and his nonsense,” a fan wrote, and the complaint is grounded in hard numbers and team consequences. While Leonard has consistently been one of the most elite two-way players in the league, these off-court problems may simply outweigh his value on the court.
Some fans reminded everyone that Ballmer publicly addressed the controversy and that the organization predicted reputational fallout in interviews and in league communications. “Ballmer did that in his interview with Romona already. This is not a surprise,” a reply said, referencing Steve Ballmer’s comments to Ramona Shelburne in which he denied prior knowledge of the Aspiration arrangement and described feeling misled by the company. The Clippers also disclosed that Wachtell Lipton Rosen Katz would lead the NBA inquiry, a step that formalized the probe and matched the tone of Ballmer’s public defense.
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Of course, that claim also appears contrary to Wong’s traceable investment in Aspiration that is shrouded with controversy. While Ballmer has suggested that his own $50 million investment came after Leonard had already signed his $176 million extension in 2021. However, the timing of the payment from Aspiration and the Dennis Wong investment that preceded it appears highly problematic.
Other reactions mixed shock at the power dynamics with a note about organizational caution, and one viral comment captured that paradox bluntly. “A team with an owner who is one of the richest people in the world is afraid of… Dennis and Kawhi. 100% believe it. Sure. Yes. Of course,” a fan wrote, and that skepticism points to recent reporting about Ballmer’s $50 million investment in Aspiration and the tangled money flows that have left the franchise exposed.