Why Kawhi Leonard no-showed $28M endorsement deal for fraudulent company involving Clippers owner Steve Ballmer

David Suggs

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Why Kawhi Leonard no-showed $28M endorsement deal for fraudulent company involving Clippers owner Steve Ballmer image

Kawhi Leonard's time with the Clippers has been fraught with scandal. The NBA conducted an investigation into his arrival in Los Angeles shortly after he signed a three-year deal with the team in 2019, while a former Los Angeles employee leveled a lawsuit against the Clips alleging that the organization tampered to secure his services.

On Sept. 3, investigative journalist Pablo Torre tossed more gas on the fire, unveiling a 3,000-page dossier looking into Leonard's contract with Los Angeles. More specifically, Torre's investigation centered on a $28 million agreement between a company owned by Leonard and one owned by Clippers owner Steve Ballmer. Leonard reportedly no-showed his endorsement deal with Aspiration, a "fraudulent tree-planting company" that went bust in March 2025.

On Sept. 5, Ballmer then responded to the allegations on a "SportsCenter" appearance.

Here's what you need to know.

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Why Kawhi Leonard no-showed endorsement deal

Torre examined Leonard and the Clippers' alleged wrongdoing at length, parsing through legal documents and dozens of interviews with former Aspiration employees to unearth Leonard's reported involvement in the scheme. Torre's investigation suggests that Leonard and his employers devised a "fool-proof" system to pay Leonard an additional $28 million to do nothing.

The scandal involved Ballmer-owned Aspiration investing millions into KL2 Aspire LLC, a company owned by Leonard. Torre found no evidence that Leonard had publicly endorsed the company. A clause in the contract allowed Leonard to "decline to proceed with any action desired by the Company," effectively letting him receive additional funds without providing any work in return.

The alleged reason for Leonard's actions — or inaction? To circumvent the NBA's salary cap rules. Leonard’s move to Los Angeles was a curious choice in the NBA world, with Torre reporting that executives were "suspicious" of how the Clippers landed him in 2019. By adding an extra $28 million to Leonard's contract value, the Clippers positioned themselves to outbid any other team.

Payments from Aspiration to KL2 Aspire LLC were reportedly sent to Dennis Robertson, Leonard's advisor who was the subject of a 2019 NBA investigation into impermissible benefits. Robertson was cleared of all wrongdoing, with the league finding that Los Angeles did not offer prohibited benefits to Leonard during his free agency. 

In Oct. 2024, former Clippers strength and conditioning coach Randy Shelton filed a lawsuit alleging that Los Angeles violated the NBA's anti-tampering rules while attempting to lure Leonard away from Toronto. Shelton claimed the Clippers exploited his pre-existing relationship with Leonard to secure undisclosed medical information and aid in their recruiting pitch. These efforts reportedly took place months before Leonard officially hit the free agency market. The NBA was unaware of the lawsuit, it revealed via a spokesperson to ESPN.

On Sept. 5, Ballmer appeared on ESPN airwaves to address the allegations brought to light by Torre. 

Ballmer said he didn't know "anything about the court documents" that Torre had brought up and that he hasn't seen them. 

"The speculation is what it is," Ballmer said. "I don't know why they did what they did. And I don't know how different it is, I really don't. And frankly, any speculation would be crazy. These are guys who committed fraud. Look, they conned me. They conned me. I made an investment in these guys."

Ballmer also broke down the timeline of the Leonard-Aspiration connection from his point of view, saying that Leonard had not even been introduced to Aspiration until two months after the alleged circumvention of the cap took place. 

"They did request to be introduced to Kawhi. Under the rules, we can introduce our sponsors to our athletes, we just can't be involved. We made an introduction, that was in early November, well past when all of this happens," Ballmer said. 

The owner also said that after recently going through all the Clippers' relations with Aspiration, texts, emails and more showed that the first introduction between Leonard and the company was in that early November timeline. From there, Ballmer said that he and the Clippers were not involved, denying that any cap circumvention took place.

"I eventually learned that they had reached a deal, I have no idea what the deal was," Ballmer said. 

Shortly after Ballmer's interview hit the airwaves, Torre confirmed that Aspiration gave Leonard an additional $20 million side deal, pushing the value of his arrangement with the firm to $48 million. The news was first reported by Boston Sports Journal.

On Sept. 5, the NBA reportedly hired the law firm Wachtell, Lipton, Rose and Katz to investigate the Leonard situation, per Sam Amick. That is the same firm that investigated both the Donald Sterling and Robert Sarver controversies.

ESPN's Ramona Shelburne reported that Aspiration bid nearly double the $550 million price tag Intuit paid for naming rights to the Clippers' home stadium.

"That gives you an indication of the kind of money that this company was throwing around back in those days," Shelburne said during a Sept. 8 appearance on "NBA Today."

What is Aspiration?

Aspiration was a "tree brokerage" firm founded by Ballmer. The company landed endorsements from Robert Downey Jr. and Drake, both of whom were paid to publicly support Aspiration. The same couldn't be said about Leonard, though, who was offered $28 million "to circumvent the salary cap", an unnamed employee said.

"The single largest payment to an individual for marketing that Aspiration ever made has completely evaded all press. ... He didn't have to do anything," the employee added. 

Aspiration filed for bankruptcy in March 2025. Leonard was listed as one of its creditors, with the company allegedly owing Leonard $7 million, according to legal documents examined by Torre.

Kawhi Leonard contract

  • Years: Three
  • Contract: $149.5 million

Leonard agreed terms to a three-year, $149.5 million ahead of the 2024-25 season. His latest deal is the third he inked with Los Angeles, following the three-year, $104 million contract he signed in 2019 and the four-year, $176 million extension he landed in 2021.

Kawhi Leonard net worth

Leonard is valued at $120 million, according to Celebrity Net Worth. He has landed a handful of glitzy business holdings over the course of his career, including a big-money New Balance endorsement and a growing real estate portfolio.

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Ultimately, though, Leonard derives most of his wealth from his on-court exploits. Leonard has made $375 million in his 14-year career. According to Spotrac, that's the eighth-highest total in NBA history.

With Leonard still making waves in his early 30s, he figures to add to that mark in the coming few seasons. He could climb higher on the list by the time he hangs up his sneakers.

Steve Ballmer net worth

Ballmer's net worth sits at $152.9 billion, according to Forbes. He's the eighth-wealthiest person in the world based on net worth.

Ballmer built his wealth in several ways. He began as an employee — and eventually an executive — at Microsoft, serving as the company’s CEO from 2000 to 2014. During this time, his net worth grew significantly, providing the "seed money" to purchase the Clippers for $2 billion in 2014.

Ballmer's wealth has continued to swell in the years since his purchase. Los Angeles is now valued at $5.5 billion, the fifth-highest mark among NBA teams, per Forbes.

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Will Kawhi Leonard, Clippers be punished?

It's unclear at the moment if Leonard and the Clippers will be punished for their alleged wrongdoing. The NBA cleared Leonard and Los Angeles of wrongdoing in its 2019 investigation into Leonard's free agency and opted against reopening the case in 2024 after Shelton's lawsuit was made public. While Torre's investigation has all the makings of a smoking gun, the league would effectively be admitting incompetence (willful or otherwise) if it were to side with Torre's findings six years after first opening an investigation into Leonard.

Still, if a punishment were to be doled out, it's likely it would be severe for organization and player alike. Following the 2000 season, the league found that the Timberwolves circumvented salary cap rules to sign Joe Smith. Minnesota was summarily docked five first-round picks (two were eventually returned) and handed a $3.5 million fine (equivalent to around $6.56 million in today's money). Then-Timberwolves owner Glen Taylor was suspended and then-Minnesota head coach Kevin McHale was forced to take a leave of absence, while Smith had his contract voided and his Bird Rights stripped away. Contemporary tampering violations have seen teams forfeit second-round picks, although given Leonard's prominence and the drawn-out nature of this controversy, it's unclear whether such a sanction would be deemed serious enough. 

The league announced that it is commencing an investigation into Torre's claims, according to ESPN's Shams Charania.

Clippers statement

A few hours after the story came out, the Clippers released an official statement. They deny the claims and even go so far as to say that they they are "absurd." A full statement can be found below. 

Who is Uncle Dennis?

Uncle Dennis refers to Dennis Robertson, Leonard's uncle, confidant and longtime advisor. Uncle Dennis has taken an active role in Leonard's NBA career over the years. That has put him at odds with team and league officials. In 2019, he was the subject of an NBA investigation into claims that he had asked for improper benefits from multiple teams while Leonard was entering free agency. Robertson's alleged requests included part ownership of a franchise, private plane access, a house and fully-guaranteed endorsement money for Leonard. No evidence was found that the Clippers accepted any of Robertson's requests, although commissioner Adam Silver said the league would re-open its investigation if additional evidence surfaced.

David Suggs

David Suggs is a content producer at The Sporting News. A long-suffering Everton, Wizards and Commanders fan, he has learned to get used to losing over the years. In his free time, he enjoys skateboarding (poorly), listening to the likes of Stevie Wonder, Marvin Gaye and D’Angelo, and penning short journal entries.