The hunger to become a championship-level franchise pushed the LA Clippers into trouble. After leading the Toronto Raptors to their first-ever championship title in June, Kawhi Leonard became an absolute favorite of the team. That’s when the Clippers snatched him in 2019. But who would have thought years later he would be the reason for their biggest downfall?
The NBA has hit the LA Clippers, Kawhi Leonard, and team owner Steve Ballmer with major penalties after finding that they broke the league’s salary-cap rules. The investigation said the Clippers helped Kawhi Leonard get business deals with four companies: Aspiration Partners, Boingo Wireless, Daktronics, and Lockton Insurance. But there was more to it.
- Investigators said the Clippers encouraged these companies to work with Leonard by offering them business opportunities with the team. In other words, it was a case of “you scratch my back, I’ll scratch yours.”
- The investigation also found that the Clippers paid some personal expenses for Leonard and people representing him.
- Leonard was also accused of pushing the Clippers to help him secure extra business opportunities through his manager, Dennis Robertson. But even after getting the opportunities, he never repaid the team for their personal expenses.
In the end, the NBA made him pay the price with a $700,000 fine. For the Clippers, the punishment hits where it hurts most: their future Draft picks. The team must give up five first-round picks, one each from the 2029, 2030, 2031, 2032, and 2033 NBA Drafts.
The team was also handed a hefty bill on top of losing its picks. The Clippers must pay a $30 million fine for the violations. Worst part? One-year suspension for Ballmer.
What hurts the most is that Kawhi Leonard is no longer with the LA Clippers. The team agreed to send the two-time NBA Finals MVP back to the Toronto Raptors in a major trade.
In return, the Clippers got Brandon Ingram and Gradey Dick, along with first-round picks in 2031 and 2033, second-round picks in 2030 and 2033, plus a 2027 first-round pick swap.
The deal was finalized on June 30, 2026, but it was put on hold on July 9 because of an NBA investigation, and the Clippers ended up losing it all. But where did the downfall actually start?
The Aspiration Connection
The story came to light on September 3, 2025, when investigative journalist Pablo Torre reported on a relationship between Kawhi Leonard and Aspiration Partners.
Torre said he had gone through many documents and spoken with former company employees while looking into the reported $28 million deal with Leonard. The report quickly caught the NBA’s attention, and an investigation began. They started looking at all the small details.
- Ballmer invested $50 million in Aspiration in 2021, according to the Los Angeles Times.
- The Clippers later signed a $300 million sponsorship deal with Aspiration.
- Then the Los Angeles Times reported in September 2025 that Aspiration was also in the running for the Clippers’ arena naming rights, but Intuit ultimately won the deal.
- Later, Torre reported that Leonard had also received about $20 million worth of equity in the company
The matter started to snowball on September 11, when Torre reported that Clippers minority owner Dennis Wong had invested nearly $2 million in Aspiration. Details emerged that Clippers owner Steve Ballmer had invested another $10 million in Aspiration in 2023.
By September 13, the pressure was mounting as several former Aspiration executives supported Torre’s reporting. They said Leonard’s deal had faced “significant objections” from senior executives and had not gone through the company’s investment committee.
What added more fuel to the fire was Torre’s report that the total capital connected to Ballmer, Wong, and the Clippers had reached about $118 million. Now, after the case was finally closed, during an appearance on Dan Patrick’s show on September 4, 2026, Pablo Torre provided a much bigger picture of how much money was associated with Aspiration.
“So Aspiration has a total value of $48 million,” Torre said on Dan Patrick’s show. “Now let’s bring in the other companies, right? Boingo Wireless, the wireless provider of the Intuit Dome, Daktronics, a scoreboard operator, and Locked-In Insurance, the insurance company for the construction of the Intuit Dome, are doing the same thing.
Those three companies, according to the NBA’s investigation through 2021, guaranteed $18 million to Kawhi Leonard. So, doing the math, that’s 66 million dollars only through, let’s call it, 2022.”
Ultimately, it all added up to one thing: trouble for the entire franchise.
How the Clippers Reached the NBA Verdict
June 1, 2026
One of Aspiration’s co-founders, Joseph Sanberg, was sentenced by a federal court to 14 years in prison because of a fraud scheme that caused at least $248 million in losses
June 30, 2026
The Clippers agreed to trade Kawhi Leonard to the Toronto Raptors, which brought back Brandon Ingram and Gradey Dick. The trade also gave them two unprotected first-round picks, two second-round picks, and a 2027 first-round pick swap.
July 9, 2026
The trade suddenly hit a roadblock. Toronto announced that the deal would remain on hold until the NBA completed its investigation.
September 2, 2026
The NBA completed its investigation and found that the Clippers had committed multiple salary-cap circumvention violations.
Then came the punishment.
A big loss for the Clippers
The $30 million fine is painful, but it is a one-time hit the Clippers can eventually move past. But the loss of five first-round picks is a bigger setback, as they lost a golden opportunity to add top players to the team.
On top of that, the Clippers are still trying to build their brand around Intuit Dome, which opened in 2024, and attract major business partners.
With a new arena and sponsors such as U.S. Bank, the team is working to create a strong business image for the long run. A salary-cap scandal can put a cloud over that effort and make sponsors and partners look down on the organization.
But what’s shocking is that this wasn’t the first time an NBA team faced such a setback. Back in 2000, the Minnesota Timberwolves found themselves in hot water after making a secret agreement with former Maryland star Joe Smith and his agent. The deal was designed to help the team sign Smith while getting around the NBA’s salary-cap rules.
The NBA came down hard on Minnesota. Commissioner David Stern took away the Timberwolves’ first-round draft picks for the next five years and fined the team $3.5 million.
Despite that, the Clippers and Kawhi Leonard didn’t back out of the deal, a mistake that not only put the organization in trouble but also affected his career.