The Clippers agreed to trade Kawhi Leonard to the Toronto Raptors on June 30. It is September 11 and he still has not been traded. Here is why.
The holdup was never really about basketball. It was about a San Francisco company called Aspiration and the question of whether the Clippers used it to pay Leonard money that should have counted against the salary cap. Leonard allegedly signed a roughly $28 million marketing deal with Aspiration that required little or no actual work. Clippers owner Steve Ballmer had invested $50 million in the company through a personal LLC in September 2021, the same month the Clippers signed a $300 million partnership making Aspiration the first founding partner of Intuit Dome.
The NBA investigated, and the punishment it handed down was the harshest cap-circumvention penalty in league history. The Clippers were fined $30 million. They forfeited first-round picks from 2029 through 2033 plus a 2029 first acquired from Indiana. Ballmer and Gillian Zucker were suspended a year without pay. Lawrence Frank was suspended six months. Leonard was fined $700,000.
What the league did not do is the part that matters for Toronto. Leonard was not suspended and his contract was not voided. The NBA reportedly found no evidence that Ballmer funneled money to Leonard through sponsors in the way the original reporting suggested. That removed the single biggest obstacle to the trade going through.
So why is it still sitting there? Because the Clippers front office is in the middle of figuring out who actually runs it. With Ballmer and Frank suspended, general manager Trent Redden is widely expected to take over as the lead decision-maker, but Los Angeles has not formally announced that. You cannot finalize a franchise-altering trade when the people authorized to sign off on it are serving suspensions and the chain of command has not been made official.
Both sides are still expected to honor the original framework. Toronto sends Brandon Ingram, Gradey Dick, two future first-round picks, two second-rounders and a first-round pick swap. The Clippers send Leonard. Reporting since the ruling has treated this as a matter of when, not if.
The Raptors deserve credit for how they handled the delay. When it became clear Toronto would be absorbing the risk of any penalties Leonard faced, they slowed down rather than rushing to completion. That was the correct play. There was a real scenario where Toronto gave up Ingram, Dick and five pieces of draft equity for a player who then got suspended for a chunk of the season. Waiting for the league to rule cost them nothing.
Now that the ruling is in, Toronto is acquiring a healthy, eligible, motivated Leonard who has talked about returning to the city where he won a title with a clean slate. That is a very different asset than the one they were nervously staring at in July.
The open question is the federal piece. Prosecutors in the U.S. attorney’s office in Brooklyn have opened a criminal investigation into the same sponsorship arrangements. That is a separate track from the NBA’s process, and nobody knows where it goes. It does not appear to be what is blocking the trade, but it is the reason this story is not finished even after Leonard puts on a Raptors jersey.
Expect the trade to be processed soon. Expect the Aspiration story to outlive it.
A longtime sports reporter, Carlos Garcia has written about some of the biggest and most notable athletic events of the last 5 years. He has been credentialed to cover MLS, NBA and MLB games all over the United States. His work has been published on Fox Sports, Bleacher Report, AOL and the Washington Post.
