The Los Angeles Clippers are facing one of the most turbulent chapters in franchise history, as reports surface regarding an investigation into Kawhi Leonard’s controversial endorsement deal with Aspiration. NBA reporter Baxter Holmes of ESPN revealed that a former Clippers staffer has urged owner Steve Ballmer to “get out” of the Kawhi business, citing concerns that the latest investigation directly challenges Ballmer’s character.
The Aspiration Endorsement Deal
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According to Pablo Torre, Leonard received $48 million from Aspiration in what has been described as a “no-show job,” allegedly designed to circumvent the NBA salary cap. Ballmer initially introduced Leonard to Aspiration in November 2021, three months after the Clippers agreed to a four-year, $173 million extension with the star forward. This introduction came shortly after the Clippers announced a $300 million partnership with Aspiration in September 2021.
Details of the payments raise further questions: Leonard received $1.7 million days after Clippers minority owner Dennis J. Wong invested nearly $2 million in Aspiration. Additionally, Leonard was granted $20 million in Aspiration shares directly from co-founder Joe Sanberg. Ballmer himself invested another $10 million in March 2023, on top of a $50 million investment made 18 months prior.
Six Seasons, Limited Returns
Since signing Leonard in 2019, the Clippers have struggled to justify the massive financial commitment. Despite Leonard’s status as a future Hall of Famer, the team has won only three playoff series in six seasons, with Leonard appearing in just 42% of games. He is set to earn $50 million in both the 2025-26 and 2026-27 seasons and will become an unrestricted free agent in 2027.
One rival GM told ESPN bluntly, “Looking back, the deal was a f—ing disaster.” Leonard’s career averages—20.1 points, 6.4 rebounds, 3.1 assists, 1.6 steals, and 0.5 blocks—underscore his talent, but the Clippers’ inability to reach the NBA Finals highlights a mismatch between expectations and results.
Ballmer’s Role Under Scrutiny
The investigation into the Aspiration deal has cast a shadow over Ballmer, who has invested at least $60 million in the company between September 2021 and March 2023. Despite this, Ballmer has maintained that he was unaware of the endorsement arrangement with Leonard.
Mark Cuban weighed in, telling Pablo Torre that Leonard’s uncle Dennis reportedly orchestrated the Aspiration deal. Cuban suggested that if Ballmer had known the deal was falling apart, he likely would have acted to protect Leonard and himself. “You don’t leave this outstanding debt out there,” Cuban explained, emphasizing the due diligence that Ballmer should have exercised.
A former Clippers staffer also raised concerns about Ballmer’s involvement, stating, “This last investigation is different. This one directly calls into question Steve Ballmer’s character. At some point, Steve has got to get out of the Kawhi business.”
Looking Ahead
As Leonard’s contract nears its final years and scrutiny intensifies over the Aspiration payments, the Clippers are left with difficult questions. Can the franchise continue building around a player whose tenure has been hampered by injuries and off-court controversies? And how much responsibility does Ballmer bear for the financial and ethical missteps associated with the deal?
For the Clippers, the next few months could define not only the team’s championship window but also the legacy of one of the NBA’s most high-profile owners and players.