After being selected 15th overall by the San Antonio Spurs in the 2011 NBA Draft, Kawhi Leonard had a rapid ascension among the NBA hierarchy. Leonard broke out in 2014–15, his fourth season in the league, when he was named Defensive Player of the Year and Finals MVP for his role in locking down LeBron James en route to the Spurs’ fifth title. However, in recent years, Leonard lost the spotlight. After signing with the Los Angeles Clippers in 2019–20, injuries cost him hundreds of games, including missing the entire 2021–22 season with a partially torn ACL in his right knee. On Sept. 3, sports reporter Pablo Torre stated on his podcast that Leonard had a $28 million dollar sponsorship deal with Aspiration — an environmentally conscious banking service — to circumvent the NBA’s salary cap.
According to ESPN’s Ramona Shelburne, the Clippers agreed to a $300 million partnership with Aspiration in September 2021. The Clippers promised Aspiration a sponsorship in their new area and a patch on their jerseys.
Three months later, Clippers owner Steve Ballmer invested $50 million of his own money into Aspiration alongside $265 million from OakTree Capital, a respected financial firm. Torre also discovered that in March 2023, Ballmer made an additional $10 million unreported investment in Aspiration.
At this time, Aspiration was floundering, bleeding cash, and laying off employees while failing to raise capital. Ballmer’s investment came three months after Clippers Vice Chairman and Ballmer’s college roommate Dennis Wong made a $1.99 million investment in the company.
Torre recently claimed on his podcast that Leonard, using his KL2 Aspire LLC, signed a four-year, $28 million endorsement deal with Aspiration in April 2022. Eight months earlier, Leonard signed a four-year $176.3 million max deal in free agency to stay in Los Angeles.
Days after Wong’s investment, Aspiration sent Leonard $1.75 million as a quarterly payment. There is no evidence that Leonard ever did any promotion for Aspiration nor any evidence of future payments to Leonard.
In March 2025, Aspiration filed for bankruptcy, reportedly $170 million in debt. The company claimed to owe the Clippers $30 million and KL2 LLC — Leonard’s company — $7 million. Just last month, Aspiration co-founder Joe Sandberg pleaded guilty to two counts of wire fraud, defrauding investors out of $248 million.
“These were guys who committed fraud,” Ballmer said on ESPN in an interview with Shelburne. “Look, they conned me. They conned me. I made an investment in these guys thinking it was on the up-and-up, and they conned me at this stage. I have no ability to predict why they might have done anything they did, let alone the specific contract with Kawhi.”
Ballmer told ESPN he was “embarrassed” for not detecting any faults in Aspiration’s investments and business model.
Before Aspiration’s deal with Leonard fell into the public eye, there was confusion among employees about the relationship. Ex-employees told The Athletic that after Sandberg initially announced the idea, executives saw little value in the proposition, which was not announced to the public.
Leonard was contractually obligated for one eight-hour production day, one four-hour public relations day, two one-hour community service events, one five-minute segment per week with Clippers Head Coach Ty Lue while Leonard was rehabbing in the 2021–22 season, and five organic engagements as requested by Aspiration on social media. Leonard, who has a reputation for being lax, was given an out to sign off on requests for anything that no longer aligned with his beliefs.
The Athletic obtained emails between Aspiration executives where they noted the deal had “pretty big flags” and questioned the marketing value Leonard could create given that he is notably reserved.
“In the months of discussion among our executives before signing the sponsorship, I don’t remember conversations about the NBA salary cap,” Andrei Cherny, Aspirations co-founder, said. “I signed the contract shortly before I submitted my resignation, but before I left there were numerous internal conversations about the various things Aspiration was planning to do with Leonard once the 2022–23 season began, including emails from the marketing team about their plans in just the week before my last day. I can’t speak to what was done or not done after I left — or why.”
Back in 1999, the Minnesota Timberwolves signed guard Joe Smith to three separate one-year contracts worth less than $3 million each, which were signed as an illegal agreement. Behind these deals was the secret promise of a seven-year $86 million contract once Minnesota retained his bird rights — a clause allowing teams to go over the salary cap to re-sign their own free agents. Simply put, since the Timberwolves could not sign Smith and stay under the cap in 1999, they attempted to find a loophole which would allow them to go over the cap to sign Smith to a long-term contract after the season’s end.
When the NBA caught wind of this transaction and violation of the salary cap, the Timberwolves were fined $3.5 million — a league record — and forfeited their next five first-round draft picks. The franchise spiraled and was unable to build a contender around 2003–04 league MVP Kevin Garnett.
The NBA is currently investigating Leonard and the Clippers. If the punishment for the Clippers and Leonard is anywhere near the framework established for the Timberwolves and Smith, the consequences could be detrimental.
