NBA Probe of Clippers’ Salary-Cap Deal with Kawhi Leonard Extends Into 2027

The NBA is investigating whether the Los Angeles Clippers violated salary-cap rules by routing money to Kawhi Leonard through a 2022 $28 million endorsement with the now-bankrupt firm Aspiration. Penalties under the 2023 collective-bargaining agreement could include fines up to $7.5 million, loss of draft picks, voiding Leonard’s contract, or suspension of team personnel. The investigation, led by law firm Wachtell Lipton, began in September 2025 and is now in its 11th month.

Report: Kawhi Leonard investigation could extend into 2027

Aspiration also maintains a 23-year, $300 million partnership with the Clippers. The probe was triggered after podcasts by former ESPN contributor Pablo Torre raised questions about the deal. The case echoes the 2000 Milwaukee Bucks scheme involving Joe Smith, which resulted in voided contracts, forfeited picks and fines.

Report: Kawhi Leonard investigation could extend into 2027

• September 2025 – Wachtell Lipton begins the NBA’s investigation.

Report: Kawhi Leonard investigation could extend into 2027

• June 30 – The Clippers and Toronto Raptors agree to trade Leonard for Brandon Ingram, Gradey Dick, unprotected first-round picks in 2031 and 2033, a 2027 pick swap, and two second-round picks.

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• July 9 – NBPA executive director David Kelly says he sees no “there, there” regarding the alleged $28 million payment.

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• July 14 – Commissioner Adam Silver calls the case “complicated,” involving bankruptcy courts and reluctant witnesses, and urges a resolution before the next season.

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• July 31 (scheduled) – The Raptors are set to finalize the trade, pending the investigation’s outcome.

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• Potential extension to 2027 – If the parties cannot agree, the dispute could move to arbitration and an appeals panel, stretching the process for several years.

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• $28 million – Size of Leonard’s 2022 endorsement with Aspiration.

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• $300 million – Value of Aspiration’s partnership with the Clippers.

Report: Kawhi Leonard investigation could extend into 2027

• $7.5 million – Maximum fine for a cap-circumvention violation.

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• 2027 – Latest year cited for a possible arbitration-driven resolution.

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NBPA representatives warned the union would move the case to arbitration if the NBA attempted to impose penalties without sufficient evidence. A source close to the union said the NBPA would “fight that to the end.”

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• Evidence status – ESPN sources note the NBPA has not seen “anything…worthy of punishment,” while the NBA has not disclosed concrete findings.

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• Investigation length – Some observers view the 11-month duration as indicative of substantive findings; others caution that length alone does not reveal the evidence’s nature.

Report: Kawhi Leonard investigation could extend into 2027

The outcome will affect the pending Leonard-Ingram trade and could set a precedent for how endorsement deals are scrutinized under the collective-bargaining agreement, influencing future contract structures and league enforcement.

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“On one hand, we want to respect everyone's rights here,” — Adam Silver, NBA commissioner

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