On September 8, 2025, a startling revelation rippled through the sports and entertainment world: Kawhi Leonard, the famously reserved Los Angeles Clippers star, reportedly earned more from his endorsement deal with Aspiration than some of Hollywood’s brightest names, including Leonardo DiCaprio, Drake, and Robert Downey Jr. According to The Athletic, Pablo Torre’s investigation into Aspiration’s financial collapse unearthed that Leonard’s deal was not only lucrative, but also at the center of a growing NBA controversy.
For those who haven’t followed the saga, Aspiration was a tree-planting company that positioned itself as an eco-conscious alternative in the financial sector. The company attracted a roster of celebrity endorsers—names like DiCaprio, Cindy Crawford, Orlando Bloom, and Drake—all known for their charisma and public presence. Yet, as The Athletic pointed out, "the guy making more than four times as much as everybody—including Cindy Crawford, Orlando Bloom, blah blah blah—was the worst of all of the athletes in that regard." That "guy" was Leonard, whose public persona is famously understated, sometimes even described as awkward or uncharismatic compared to his celebrity peers.
The numbers are staggering. Documents reviewed by Torre revealed that Leonard’s endorsement arrangement with Aspiration was valued at $28 million—an amount that dwarfed the payouts to other high-profile endorsers. While DiCaprio, Drake, and Robert Downey Jr. brought significant public influence and star power, Leonard’s earnings from Aspiration eclipsed theirs by a factor of four or more. In an era where celebrity endorsements are often tied to social media reach and public engagement, Leonard’s windfall left many scratching their heads.
But the intrigue doesn’t end with the question of why Leonard was so well-compensated. The deal has now drawn the attention of the NBA itself. According to The Athletic, the league is investigating whether the Aspiration endorsement was used as a means of salary cap circumvention, particularly in connection to Leonard’s 2019 decision to sign with the Clippers. NBA spokesman Mike Bass confirmed that the arrangement is under review, and that the league has retained the law firm Wachtell, Lipton, Rosen & Katz to oversee the investigation. This is the same firm that handled high-profile NBA probes in the past, including the Donald Sterling and Robert Sarver cases.
At the heart of the matter is whether Leonard’s massive Aspiration payout was in any way connected to his decision to join the Clippers. The team’s owner, Steve Ballmer, is reported to have held a small stake in Aspiration—less than three percent, according to Ballmer—raising concerns about a potential conflict of interest. Ballmer has firmly denied any wrongdoing, insisting that Leonard’s contract was negotiated independently and that his own investment in Aspiration was too minor to have influenced the player’s decision.
Still, the optics have raised eyebrows across the league. As Torre reported, documents showed that as Aspiration’s financial situation worsened and the company spiraled toward bankruptcy, Leonard was treated as a top-priority client. Payments to him continued, even as other obligations went unpaid. This preferential treatment has become a focal point for investigators, who are keen to determine whether the endorsement was a legitimate business arrangement or a vehicle for funneling additional compensation to Leonard outside of NBA salary cap regulations.
The stakes are high. If the NBA determines that rules were broken, the consequences could be severe. As insider Sam Amick noted, potential penalties include voiding player contracts, suspending executives, or imposing significant financial sanctions. The last time the league faced a major salary cap circumvention case was in 2000, when the Minnesota Timberwolves were penalized for their secret deal with Joe Smith. That episode resulted in the voiding of Smith’s contracts and the loss of multiple first-round draft picks for the Timberwolves.
The Clippers, for their part, have maintained that the Aspiration deal had no bearing on Leonard’s NBA contract or his choice to join the team. Team executives are expected to be interviewed as part of the league’s ongoing investigation. According to The Athletic, the NBA is determined to get to the bottom of the matter, not just for the sake of this particular case, but to set a precedent for how endorsement deals are handled moving forward. The outcome of the investigation is expected to shape the league’s approach to player endorsements, influence, and the ever-present challenge of salary cap enforcement.
For many observers, the case also highlights broader questions about the role of endorsements in professional sports. In recent years, as player salaries have soared and off-court earnings have become a significant part of athletes’ income, the potential for conflicts of interest and regulatory gray areas has grown. The NBA’s salary cap is designed to ensure competitive balance, but as this saga shows, the lines between on-court and off-court compensation can sometimes blur.
Adding to the complexity is the fact that Aspiration itself is now in bankruptcy. Once touted as a visionary company blending environmentalism with finance, Aspiration’s collapse has left a trail of unpaid debts and disappointed investors. Yet, throughout its financial troubles, the company reportedly continued to prioritize payments to Leonard, treating him as a "top client" even as other commitments fell by the wayside. This not only underscores the importance Aspiration placed on its relationship with Leonard, but also raises questions about the company’s internal decision-making and financial stewardship.
As the NBA’s investigation unfolds, all eyes are on the league’s next steps. Will the probe uncover evidence of wrongdoing, or will it ultimately vindicate Leonard, Ballmer, and the Clippers? Whatever the outcome, the case has already sparked a broader conversation about transparency, fairness, and the evolving landscape of athlete endorsements. For now, the only certainty is that the intersection of sports, business, and celebrity remains as unpredictable—and as fascinating—as ever.
As the dust settles, fans and insiders alike are left to ponder the implications of a deal that saw the NBA’s quietest superstar out-earn some of the world’s most famous faces, all while a struggling company bet big on his understated appeal.
