Kawhi Leonard has long been a figure who sparks conversation, whether for his clutch playoff performances or his enigmatic presence off the court. Now, more than five years after arriving in Los Angeles, Leonard’s name is again dominating headlines — this time for reasons that extend beyond basketball.
The latest controversy surrounding the Clippers forward focuses on the circumstances of his initial 2019 contract with the franchise. According to a recent investigation, Leonard and the Clippers may have worked together to sidestep NBA salary cap rules, potentially securing the superstar tens of millions in undisclosed financial benefits. The allegations, if proven true, could have serious implications for both Leonard and the organization.
The 2019 Free Agency Sweepstakes
Fresh off leading the Toronto Raptors to the 2019 NBA championship, Leonard was the league’s most coveted free agent. His next destination boiled down to three options: staying in Toronto, joining LeBron James and Anthony Davis with the Los Angeles Lakers, or moving to the Clippers, who were aggressively pursuing him as the centerpiece of a new era.
The Clippers ultimately won the race, but according to reports, Leonard’s camp — led by his advisor and uncle, Dennis Robertson — set unusually high demands during negotiations. These demands reportedly went well beyond the confines of traditional NBA contracts.
According to The Athletic’s Sam Amick, Robertson pushed for a package that included ownership stakes in companies, corporate sponsorships, and even so-called “no-show” endorsement deals. These arrangements would have allowed Leonard to pocket millions without needing to fulfill promotional obligations.
Pablo Torre’s Investigation
Investigative journalist Pablo Torre dug deeper into the matter, examining legal documents and interviewing former employees of Aspiration, a Los Angeles-based “tree-planting” firm tied to Clippers owner Steve Ballmer. Torre reported that Leonard used his company, KL2 Aspire LLC, as the vehicle to partner with Aspiration.
The investigation revealed that Leonard allegedly received an extra $28 million in funding through this arrangement. On top of that, Aspiration reportedly offered him an additional $20 million, bringing the potential total to $48 million. Payments were allegedly funneled through KL2 Aspire LLC, with Robertson acting as the intermediary.
Aspiration collapsed into bankruptcy in March 2025, and Leonard was listed as one of its creditors, reportedly owed $7 million. Torre’s reporting suggests the company served as a key player in circumventing NBA salary cap restrictions, raising questions about the legality of Leonard’s deal with the Clippers.
Steve Ballmer Denies Allegations
Clippers owner Steve Ballmer publicly denied any wrongdoing during a September 5 appearance on ESPN. He distanced himself and the organization from the allegations, while admitting he too was misled by Aspiration’s executives.
"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 outlined his version of the timeline, stating that Leonard had not even been introduced to Aspiration until two months after the alleged violations occurred.
"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 explained.
The Aspiration Connection
Aspiration branded itself as a “tree brokerage” company, a green-tech firm that attracted celebrity endorsements from the likes of Robert Downey Jr. and Drake. But behind the eco-friendly branding, the firm was hemorrhaging money.
One former employee described Leonard’s contract with Aspiration as unprecedented, calling it "the single largest payment to an individual for marketing that Aspiration ever made."
The employee added: "He didn't have to do anything."
The fact that such payments were linked to Leonard’s camp, particularly during the same period he was negotiating with the Clippers, has fueled concerns that the arrangement was a deliberate attempt to skirt league rules.
NBA Prepares to Investigate
Following Torre’s report, the NBA announced it was reopening its investigation into Leonard’s 2019 signing. The league had previously examined claims that Robertson sought improper benefits from teams but cleared both Leonard and the Clippers at the time.
This new evidence, however, could change the equation. The most infamous precedent dates back to 2000, when the Minnesota Timberwolves were punished for illegally arranging a side deal with forward Joe Smith. That scandal cost the franchise five first-round draft picks (two later restored) and a $3.5 million fine, while Smith’s contract was voided.
If the NBA determines Leonard and the Clippers circumvented the salary cap, the penalties could be severe — potentially impacting the team’s draft assets, finances, and even Leonard’s eligibility.
Leonard’s Current Contract and Clippers’ Salary Cap
Despite the controversy, Leonard remains one of the NBA’s highest-paid stars. Ahead of the 2024-25 season, he signed a three-year, $149.5 million deal with the Clippers — his third contract with the franchise after a three-year, $104 million pact in 2019 and a four-year, $176 million extension in 2021.
The Clippers’ financial situation underscores the stakes of the case. According to Spotrac, Los Angeles is operating with over $200 million in salary allocations. The team sits $48.96 million over the cap but remains just inside the first apron. Leonard’s $50 million annual salary, paired with James Harden’s $39.18 million deal, accounts for the bulk of their payroll.
Given those figures, the notion that additional financial benefits were arranged outside of official salary structures could land both Leonard and the organization in hot water.
What Happens Next?
The outcome of the NBA’s probe remains uncertain. Punishments for tampering and cap circumvention have historically varied, with some teams losing second-round picks while others, like Minnesota in 2000, faced massive sanctions.
Given Leonard’s profile as one of the league’s premier stars, and the scale of the alleged benefits, the NBA may be forced to act decisively. Whether the Clippers face fines, draft penalties, or further restrictions will depend on the evidence the league uncovers in the coming months.
For now, Leonard continues to compete at an elite level, but his legacy — and the Clippers’ long-term future — may hinge as much on this off-court investigation as their on-court performance.
