Report: Clippers living in fear of upsetting Kawhi Leonard since 2019

The Clippers landed Kawhi Leonard in 2019, and at the time it felt like a franchise-altering win. But as ESPN’s Baxter Holmes details, the relationship has been a rocky one — filled with injuries, lawsuits, investigations and a whole lot of organizational anxiety.

Since Leonard’s arrival, the Clippers have won just three playoff series, while the two-time Finals MVP has suited up for only 58% of possible games.

Off the court, the team has been sued twice for alleged tampering, fined multiple times over Leonard-related violations, and is now facing its most serious probe yet — an NBA investigation into possible salary-cap circumvention tied to his Aspiration endorsement deal.

“This last investigation is different,” one former Clippers staffer told Holmes. “This one directly calls into question Steve Ballmer’s character. At some point, Steve has got to get out of the Kawhi business.”

Demands and Accommodations

Holmes reports that Leonard’s uncle, Dennis Robertson, came to the 2019 free agency meetings with a laundry list of requests: part ownership of the franchise, a private plane, a house, guaranteed endorsement money.

The same demands were made to the Raptors and Lakers. The Clippers, sources say, didn’t agree to those (they weren’t even legal under the CBA), but they did loosen other rules.

Leonard was allowed to live in San Diego and commute by helicopter, skip select media and community obligations, and bring members of his personal circle into the organization.

The Clippers also adopted a “strict protocol” for how staff could speak publicly about Leonard — basically, not at all.

Doc Rivers broke that code during Leonard’s first season when he casually said Kawhi “feels great” while the star sat out due to load management. The league fined L.A. $50,000, but Leonard’s camp appreciated the silence.

As one former staffer put it: “If this guy is willing to tell the Spurs — maybe the most respected team in pro sports — to go f— themselves, he’s not going to hesitate to tell us. Everybody was afraid of Kawhi leaving.”

“Sacred Secrets” and Strained Tensions

Inside the building, Leonard’s health was treated like classified information. Press releases and social media posts mentioning him often required approval from both team leadership and Leonard’s camp.

One ex-employee said it created “extreme angst” in the medical department: “It was like the Clippers’ medical staff wasn’t really allowed to touch Kawhi ever.”

What’s Next?

The fear factor has cooled some. Leonard could’ve signed a four-year, $220 million extension in 2023 but instead accepted a three-year, $153 million deal — signaling to the team he wasn’t bolting.

Still, rival execs told Holmes they expect this to be the final contract of Leonard’s Clippers tenure.

“They’re done building around Kawhi,” another former staffer said. “They know that and he knows that.”

Leonard’s current deal runs through the 2026-27 season.