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The Los Angeles Clippers pursued Kawhi Leonard in 2019 with the hope of building a perennial contender. Years later, the results tell a far more complicated story. What was expected to usher in a championship era has instead been overshadowed by courtrooms, league investigations, and underwhelming postseason results.

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Since his arrival, the Clippers have won just three playoff series (vs Mavs in 2020 and 2021, vs Jazz in 2021) while being tied to four separate legal or league actions: Doc Rivers’ $50,000 tampering fine in 2019, Johnny Wilkes’ 2020 lawsuit alleging a backdoor deal, Randy Shelton’s ongoing tampering and medical mishandling claims, and the more recent $28 million Aspiration endorsement controversy. Together, these cases highlight a turbulent off-court chapter that has run parallel to Leonard’s tenure.

Since even before Kawhi signed with the Clippers, he has been a legal and health headache,” Brian Windhorst said on The Hoop Collective podcast. “All the way back in May of 2019, Doc Rivers, the then coach, was fined 50 grand for making tampering comments… Since the minute they signed him, the Clippers have been paying legal fees—there’s either been an NBA investigation or a lawsuit ongoing for the entire time Kawhi Leonard has been a Clipper.”

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Tim Bontemps summed it up, saying, “All you got to say is three playoff series victories, four combined lawsuits and investigations, including this one since the signing. It’s all you got to say.” Each of these cases has demanded significant attention and resources: While on the floor, Leonard has undergone three knee surgeries and, out of a total of 472 games since 2019, has played only 266. He even missed the entire 2021-22 season on account of his injuries.

For a franchise that mortgaged its future with the Paul George trade and years of draft capital, the payoff has been modest at best. The Clippers remain without a Finals appearance in the Leonard era, and the combination of legal entanglements, injuries, and underachievement has defined this chapter of their history.

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Off-Court Distractions Outpacing On-Court Ambitions

Beyond the lawsuits already documented, the Clippers’ constant entanglements have shaped their operational flow in ways that rarely make headlines. “There’s either been an NBA investigation or a lawsuit ongoing for the entire time Kawhi Leonard has been a Clipper,” Brian Windhorst said, pointing to the strain it places on the organization’s long-term planning.

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The resources needed to navigate these situations, legal fees, compliance reviews, and executive time, have at times delayed or altered trade decisions and contract talks. Tim MacMahon added that this pattern has become a defining feature of the Leonard era: “Never mind that the return [from the Paul George trade] was the foundation of a championship team elsewhere. The Clippers have been tied up off the floor more than on it.”

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The accumulation of these cases paints a broader picture of instability during Leonard’s tenure. From the tampering fine in 2019 to the ongoing disputes today, the Clippers have often found themselves managing off-court issues just as much as on-court aspirations.

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