Since Kawhi Leonard joined the Los Angeles Clippers in 2019, a cloud of concern has hung over the franchise—fear of upsetting the star forward and his entourage. Although securing Leonard was seen as a pivotal moment for the team, it hasn’t unfolded as expected.

Injuries, began during his time with the Spurs, have plagued Leonard throughout his Clippers tenure, limiting him to just 58% of possible games and yielding only three playoff series victories. As Baxter Holmes from ESPN reports, the Clippers have faced legal troubles as well; they’ve been sued twice for tampering and have been fined multiple times for violating league rules related to Leonard.

The current investigation raises serious questions about Clippers' owner Steve Ballmer’s integrity, prompting some insiders to suggest it might be time for the franchise to reconsider their ties to Kawhi.

A Complex Recruitment Process

During the 2019 free agency frenzy, the Clippers learned quickly that negotiating with Leonard’s camp would not be straightforward. Reports reveal that Leonard’s uncle, Dennis Robertson, presented a set of staggering demands, including team ownership stakes and guaranteed off-court endorsement deals—requests that were ultimately deemed unacceptable under league rules.

While some demands were not met, the Clippers did accommodate Leonard in other ways. He was allowed to live in San Diego, skip certain media events, and even bring some of his personal associates into the organization.

Managing Public Perception

Robertson also insisted on strict guidelines on how team officials could discuss Leonard publicly. This created tension within the organization, especially after former coach Doc Rivers unintentionally violated the protocol, leading to a hefty fine for the team.

As years passed, Leonard’s relationship with the Clippers grew complicated, with many in the organization aware of how quickly things soured between him and the Spurs over an injury dispute.

Secrets and Sensitivities

Details regarding Leonard’s health became treated like high-level secrets within the Clippers. Every public mention of him required approval from top executives and sometimes even from his representatives. This heightened sensitivity bred friction within the Clippers' ranks, particularly in their medical department, which felt unable to properly manage his care.

A Shift in Dynamics?

Recently, concern over Leonard's departure seems to be easing. He recently signed a three-year deal worth $153 million—significantly less than the four-year, $220 million extension he was eligible for. Observers believe this may signify a turning point for both Leonard and the Clippers.

As his contract runs through the 2026/27 season, many insiders predict it may signal the conclusion of Kawhi’s chapter with the team. A former staffer noted, "They’re done building around Kawhi," indicating a seismic shift in how the franchise views its future.