Kawhi Leonard, Steve Balmer, Los Angeles Clippers
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INGLEWOOD, CALIFORNIA - APRIL 24: Kawhi Leonard #2 of the Los Angeles Clippers reacts after defeating the Denver Nuggets in Game Three of the Western Conference First Round NBA Playoffs at Intuit Dome on April 24, 2025 in Inglewood, California.
Kawhi Leonard’s name is suddenly back in the middle of NBA controversy. New reporting out of Toronto suggests the 2019 Finals MVP didn’t just walk away from the Raptors after their championship season—he and his camp reportedly made demands that insiders called “long and absurd.”
According to the Toronto Star, Leonard’s uncle and trusted adviser, Dennis Robertson, allegedly asked for ownership stakes in outside companies tied to Maple Leaf Sports & Entertainment, as well as $10 million annually in guaranteed sponsorship income. The kicker? Leonard wouldn’t have to do anything for the money. When told sponsors would expect ads or appearances, Robertson reportedly shut it down with a simple line: “We don’t want to do anything.”
Toronto passed. Leonard left for the Los Angeles Clippers. And now the similarities between those rejected requests and the Clippers’ alleged salary cap scheme are hard to ignore.
Kawhi Leonard’s camp demands to the Toronto Raptors in 2019 free agency:
• A trade for Paul George
• An extra $10M in sponsorship income, bluntly stating: “We don’t want to do anything.”
• Partial ownership of the Toronto Maple Leafs
• Ownership stakes in other companies… pic.twitter.com/foMJ7AojzT
— NBACentral (@TheDunkCentral) September 9, 2025
Raptors Said No, Clippers Said Yes
The demands Robertson allegedly made in 2019 now read like a blueprint for what Leonard later received in Los Angeles. Aspiration, a start-up heavily backed by Clippers owner Steve Ballmer, reportedly funneled Leonard $28 million through a “no-show” endorsement deal. He also apparently received $20 million in company stock.
The Clippers denied wrongdoing, but the league has launched a formal investigation. The Athletic reports the case will dominate discussions at the NBA’s September board of governors meeting.
Clippers Under NBA Scrutiny
If true, this wouldn’t just be a violation. It would be the biggest case of salary cap circumvention in league history—tens of millions allegedly flowing off the books to keep Leonard in Los Angeles. The NBA has retained the New York law firm Wachtell, Lipton, Rosen & Katz to conduct its probe. It’s the same group used in the high-profile investigations of Donald Sterling and Robert Sarver. Both men were ultimately pressured to sell their teams.
For the Clippers, the timing could not be worse. Their championship window is already under pressure. Now, they may face penalties that could reportedly reshape the franchise.
Toronto Got the Ring, Los Angeles Got the Headache
Getty Kawhi Leonard formerly of the Toronto Raptors celebrates with the Larry O’Brien Championship Trophy after his team defeated the Golden State Warriors to win Game Six of the 2019 NBA Finals.
The Raptors reportedly walked away from Leonard’s “absurd” requests in 2019, but not before he delivered their first and only championship. That single season remains one of the great one-year runs in NBA history.
The Clippers got Leonard long-term—and with him, years of injuries, playoff heartbreak, and now a scandal that could apparently change everything.
Toronto kept its dignity. Los Angeles may end up paying the price.