Will Kawhi Leonard Become a Free Agent? 29 NBA Teams on High Alert Amid $28M Aspiration Controversy

The NBA hasn’t handed out a major salary cap punishment in over 25 years, not since the Timberwolves’ infamous 1999 Joe Smith case. Back then, Minnesota got slammed with a $3.5M fine, lost five first-round picks, and saw Smith’s contract voided—a hit that crippled their Kevin Garnett era. Now, a new situation is brewing, and this time it involves the LA Clippers and Kawhi Leonard. Reports suggest owner Steve Ballmer and Kawhi are tied to alleged salary cap circumvention. But what does this really mean for Kawhi moving forward?

The whole situation exploded when journalist Pablo Torre dropped a bombshell on his podcast, revealing leaked documents tying Kawhi Leonard, Steve Ballmer, and the LA Clippers to an alleged salary cap circumvention scheme. According to Torre, Kawhi signed a $28 million marketing deal in 2021 with an environmental start-up, Aspiration, which was partly funded by Ballmer himself. The NBA is now officially investigating the allegations, as NBA spokesman Mike Bass told ESPN, saying, “We are aware of this morning’s media report regarding the LA Clippers and are commencing an investigation”—a development first reported by Shams Charania on X. And if true, this could have massive implications not just for the Clippers but for Kawhi Leonard’s future.

Now, here’s where it gets complicated for Kawhi. Back in 2019, after winning a championship with the Raptors, he joined the Clippers on a three-year, $104 million deal, with an opt-out clause after the 2020-21 season which he used, becoming a free agent. In 2021, Kawhi re-signed with LA on a four-year, $176 million extension, and later, in 2024, inked another three-year, $153 million deal. On paper, his 2021 extension added about $3M more per season, but Torre’s report suggests a secret side arrangement through Aspiration could have bumped that figure by an extra $7M annually, effectively making Kawhi earn $10M more each year. If proven, the NBA could potentially void parts of his contract and that could possibly make Kawhi a free agent again.

Then came the real bombshell. A former Aspiration finance department employee, speaking under anonymity, claimed they were instructed not to ask questions about Kawhi’s deal because it was explicitly organized by the Clippers to circumvent the salary cap. According to Torre, Aspiration agreed to pay Kawhi $28M in four yearly installments of $7M each, starting in 2022 and ending in 2026.

Conveniently, that timeline matches his Clippers extension perfectly. Even more suspicious? Kawhi allegedly never promoted Aspiration: no ads, no commercials, no social media posts, nothing. A clause in the contract reportedly even allowed Leonard to “decline to proceed with any action desired by the company” and still get paid, as long as he remained a Clipper.

This arrangement looks even murkier when you zoom out. Weeks after Kawhi re-signed in 2021, Ballmer invested $50M into Aspiration, and the Clippers announced a 23-year, $300M sponsorship deal with the company. But by 2023, Aspiration filed for bankruptcy, leaving behind $30M owed to the Clippers, $11M to Ballmer’s Forum Entertainment, and $7M to Kawhi’s company, KL2 Aspire LLC. Bankruptcy filings list Leonard’s company as a creditor, and if the payments were linked directly to him staying with the Clippers, the NBA could interpret this as a direct salary cap violation.

That opens the door to serious consequences, including voiding Kawhi’s deal, potential fines, and even the possibility of unrestricted free agency if his contract is ruled invalid.

So, where does this leave Kawhi Leonard? If the NBA finds sufficient evidence, there are several possible outcomes. The league could impose player fines of up to $350,000, suspend personnel, or, in extreme cases, void Kawhi’s current contract, making him a free agent before 2026. But there’s also the possibility Kawhi clears his name if the league determines he wasn’t directly involved in structuring the deal.

Given that he signed a three-year, $153M extension in 2024, the stakes couldn’t be higher, both financially and reputationally.

The NBA warns all 29 teams: Salary cap tricks could cost you big

Salary cap circumvention, as laid out in Article XIII, Section 1(b) of the NBA’s Collective Bargaining Agreement, basically happens when a team finds a sneaky way to pay a player more than his contract allows. Usually, this involves a third party like a sponsor or business partner stepping in to cover extra payments that go beyond the legal limits.

If the money paid is way above fair market value while the player’s contract itself is below market value, that’s where the NBA steps in. One common example could be giving a player a cheap contract now but secretly planning to pay him big later using Bird Rights, or setting up endorsement deals through companies tied to the owner. The league watches this closely because it gives teams an unfair advantage, but proving it is actually pretty rare.

To understand how strict the league can be, there have been a few notable cases over the years apart from the Joe Smith situation. Back in 1993, the NBA questioned the Portland Trail Blazers over a seven-year, $11 million contract they gave Chris Dudley, which included an unusual opt-out after the first season. At that time, a player could gain full Bird Rights with a new team after just one year, meaning Dudley could’ve opted out and re-signed for way more money above the cap.

However, the deal was upheld in arbitration since Dudley got injured and never used the opt-out. Then, in 1996, David Falk, Michael Jordan’s agent, reportedly explored a plan for Jordan to sign with the New York Knicks. Since the Knicks and Sheraton Hotels were both owned by ITT Corporation, the idea was allegedly to supplement Jordan’s salary with a $15 million endorsement deal from Sheraton, bypassing the salary cap.

But no primary NBA documentation confirms the plan’s details or that it was formally investigated. Jordan re-signed with the Chicago Bulls in 1996 for a one-year, $30.1 million contract

Fast forward to today, and the penalties for salary cap circumvention depend entirely on the type of violation. For a Section 1 violation, the NBA can fine up to $4.5M for a first offense, $5.5M for later ones, void contracts, and even take away a first-round pick.

But a Section 2 violation is much harsher—fines up to $7.5M, suspensions up to a year, voided deals, and loss of draft picks with no set limit. Basically, the punishment for the Clippers will depend on what the ongoing investigation uncovers.

Speaking of the Clippers, this isn’t their first time being linked to these kinds of issues. Back in 2015, the team was fined $250,000 for offering DeAndre Jordan an unauthorized $200,000-per-year Lexus endorsement deal, just months after Steve Ballmer bought the franchise.

As for Kawhi Leonard, neither he nor the Clippers have ever been proven guilty of salary cap circumvention, but the rumors have been around since 2019, when Kawhi signed his three-year, $103M deal.

Reports claimed his uncle, Dennis Robertson, allegedly asked teams like the Lakers and Raptors for benefits well beyond league rules, things like part ownership, a private jet, a house, and guaranteed off-court endorsement money.

The NBA looked into those allegations but found no evidence linking the Clippers to any wrongdoing. Then, in 2020, a man named Johnny Wilkes even sued the Clippers and Jerry West, claiming he was promised $2.5M for helping land Kawhi. That lawsuit was eventually dismissed in 2022, but the league made it clear it would reopen investigations if new evidence ever surfaced.

The Clippers, however, have consistently maintained their innocence. In a statement to Pablo Torre, the team said that neither Steve Ballmer nor the organization engaged in salary cap circumvention or any misconduct involving Aspiration, calling all claims “provably false.”

Interestingly, former Mavericks owner Mark Cuban also weighed in on social media, siding with Ballmer and writing that he’s “Team Ballmer.” Cuban argued that Steve Ballmer is “not that dumb” and questioned why Ballmer would risk everything only to have the company go bankrupt, making everything public anyway. Kawhi Leonard, meanwhile, has not made any public comments on the situation yet.