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Latest On Kawhi Leonard, Clippers

September 10, 2025 by Hoops Rumors

Bruce Arthur of The Toronto Star (subscription required) has added another fascinating detail to the Kawhi Leonard/Clippers saga, reporting that when the Raptors were negotiating with Leonard in 2019’s free agent period, his camp asked the team for an arrangement that lines up with the deal the star forward eventually got with the company Aspiration. According to Arthur, the demands made by Leonard’s uncle and representative, Dennis Robertson, included $10MM per year in extra sponsorship income.

The Raptors weren’t permitted to negotiate or have any involvement in those off-court sponsorship deals, but suggested there would be corporate sponsors eager to have Leonard as a promoter. However, they were told by Leonard’s camp that he didn’t want to have to do anything for that extra money, such as filming advertisements or making promotional appearances.

“That’s when the Raptors realized Leonard wasn’t asking to be introduced to Toronto’s lucrative corporate community,” Arthur writes. “They were being asked to arrange no-show jobs, and arrange no-investment investments. (They) rejected both proposals.”

Arthur previously reported that Leonard’s camp asked for a stake in the NHL’s Toronto Maple Leafs, who share an ownership group with the Raptors.

Leonard and the Clippers are being investigated by the NBA after reports indicated that Aspiration – a Clippers sponsor that received a $50MM investment from team owner Steve Ballmer – agreed to pay the two-time Finals MVP $28MM, plus an additional $20MM in company stock.

While it was ostensibly an endorsement deal, Leonard wasn’t contractually obligated to actually do anything to earn that $28MM, which represented an unusually high amount for any sort of off-court sponsorship agreement. The league is looking into whether the Clippers were essentially funneling money to Leonard via Aspiration in order to circumvent the salary cap.

Here are a few more notes on the subject:

  • Appearing on NBA Today on Monday (Twitter video link), ESPN’s Ramona Shelburne reported that Aspiration offered almost double the $550MM that Intuit did for the naming rights to the Clippers’ arena, but the Clippers opted to go with the more well-established brand. “That gives you an indication of the kind of money that (Aspiration) was throwing around back in those days,” Shelburne said.
  • During that same NBA Today segment (Twitter video link), ESPN’s Dave McMenamin said that a Clippers source likened a tampering violation to a speeding ticket and salary cap circumvention as a “murder charge,” the implication being that the team knows not to cross that red line. The team has conveyed that it is “welcoming” the NBA’s investigation into the matter, McMenamin adds.
  • Eric Pincus of Bleacher Report explores three potential outcomes of the NBA’s investigation into the Clippers and Leonard, ranging from the Clippers getting off scot-free to the organization (and Leonard) facing a Timberwolves/Joe Smith-style punishment. When the NBA learned in 2000 that the Timberwolves had entered into an illegal contract with Smith to circumvent the cap, it fined the organization $3.5MM, took away five first-round picks (two were later returned), and voided Smith’s contract.

Filed Under: Raptors

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