Kawhi Leonard

The Clippers have been operating under the fear of upsetting Kawhi Leonard and his representatives ever since he signed with the team in 2019, sources tell Baxter Holmes of ESPN.

Landing Leonard was viewed at the time as a major win for the franchise, but Holmes notes that it hasn’t completely worked out that way. Injury problems that began in San Antonio have persisted, leaving him available for just 58% of the games during his time with the Clippers, and the team only has three playoff series victories since Leonard’s signing.

In addition, Holmes states that the Clippers have been sued twice for alleged tampering violations since 2019, they’ve been fined at least twice for violations of league rules involving Leonard and they’ve been the subject of at least three NBA investigations, including the current probe of potential salary cap circumvention involving Leonard’s endorsement deal with Aspiration.

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

The Clippers learned during the 2019 free agency pursuit that life with Leonard would be complex. A source with knowledge of the negotiations tells Holmes that Leonard’s uncle, Dennis Robertson, submitted a list of demands that included part ownership of the team, access to a private plane, a house and guaranteed off-court endorsement money. The source adds that Robertson made the same demands to the Raptors, Leonard’s current team at the time, and the Lakers, who were also heavily involved in the bidding.

Another source tells ESPN that the Clippers didn’t agree to those demands because they weren’t permissible under the collective bargaining agreement, but they did acquiesce to other requests. When he first joined the team, Leonard was permitted to live in San Diego and commute to L.A. by helicopter. He was also allowed to skip certain media obligations and team community events, and he got to bring some of his own circle into the organization.

A team source denies those allegations, telling Holmes that Leonard’s camp never made some of the reported requests and others were mischaracterized.

Another demand from Robertson was a “strict protocol” on how team officials would talk about Leonard publicly, which meant saying nothing unless it was necessary. Doc Rivers, who was the team’s head coach at the time, ran afoul of that policy early in Leonard’s first season when he told reporters that Leonard “feels great” on a night that he sat out a game due to load management. The organization refused to elaborate and was fined $50K by the league, but its silence was seen as a show of loyalty by Leonard and his camp.

A former staffer indicated to Holmes that the Clippers were wary of alienating Leonard after seeing how quickly his relationship with the Spurs dissolved over an injury dispute.

“The Spurs were maybe the most respected, most revered pro sports team in America,” the ex-employee said. “It was like if this guy is willing to tell those people to go f— themselves, he can’t possibly be afraid to tell us to go f— ourselves. … Everybody was afraid of Kawhi leaving.” 

Multiple sources indicated to Holmes that details about Leonard’s health were considered to be “sacred secrets.” News releases and social media posts that mentioned Leonard were reviewed by senior leadership before being distributed, and sometimes they were submitted to Leonard’s representatives for their approval. The sensitivity regarding Leonard’s physical condition and the fear of upsetting him led to tensions inside the organization.

“It caused extreme angst within the medical department,” another former staffer said. “It was like the Clippers’ medical staff wasn’t really allowed to touch Kawhi ever.”

The fear of Leonard’s departure seems to have lessened somewhat in recent years, Holmes adds. He was eligible for a four-year, $220MM extension entering the 2023/24 season, but he ultimately settled for a three-year deal at $153MM. Clippers officials were confident that Leonard would accept the reduced offer rather than pursue free agency, where suitors would have required a medical exam.

Leonard’s latest deal runs through the 2026/27 season, and Holmes reports that multiple general managers and other executives he spoke with expect it to mark the end of his time with the Clippers.

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