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Doc Rivers, Leonardo DiCaprio Reportedly Were Among Celeb Investors in Aspiration Co.

Mike ChiariSep 13, 2025

Aspiration, the company at the center of an NBA investigation into whether the Los Angeles Clippers circumvented the salary cap with improper payments to Kawhi Leonard, reportedly had several big-name investors before filing for Chapter 11 bankruptcy in March.

According to ESPN's Shwetha Surendran, U.S. Securities and Exchange Commission filings show that former Clippers and current Milwaukee Bucks head coach Doc Rivers was among the investors, as were actors Leonardo DiCaprio, Robert Downey Jr. and Orlando Bloom, and model Cindy Crawford.

Journalist Pablo Torre reported last week that an unnamed Aspiration employee told him the four-year, $28 million endorsement deal Leonard signed with the company in April 2022 was done to "circumvent the salary cap."

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Clippers owner Steve Ballmer made a $50 million investment into Aspiration in September 2021, and the Clippers and Aspiration entered into a $300 million partnership that same month, complete with Aspiration patches on the Clips' jerseys.

Leonard—a six-time All-Star, two-time NBA champion and two-time NBA Finals MVP—signed a four-year, $176.27 million contract extension with the Clippers in August 2021, just months before the Aspiration endorsement deal.

Ballmer told ESPN's Ramona Shelburne last week that Aspiration officials asked him to introduce them to Leonard, and he did so in November 2021, which led to the endorsement deal.

He added that he had no knowledge of or influence over the endorsement agreement between Aspiration and Leonard.

While Ballmer has denied any wrongdoing, the NBA is investigating the situation, with NBA Commissioner Adam Silver telling reporters this week that "the burden is on the league" to prove salary cap circumvention took place before taking any disciplinary action.

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