Kawhi Leonard Receives Significant Payment from Aspiration

In December 2022, Los Angeles Clippers star Kawhi Leonard received a quarterly endorsement payment of $1.75 million from Aspiration, just days after a financial investment made by Clippers vice chairman Dennis J. Wong raised questions about the company's stability.

Timing of Payments Sparks Investigation

Newly surfaced documents revealed that Leonard's payment occurred on December 15, 2022, precisely nine days following a $1.99 million wire transfer from Wong’s DEA 88 Investments LLP to Aspiration, which was reportedly on the verge of bankruptcy. Wong’s investment took place on December 6, 2022, raising concerns about the nature and timing of these transactions.

Leonard had entered into a four-year, $28 million endorsement deal with Aspiration through his company KL2 Aspire LLC in April 2022, after agreeing to a four-year, $176.3 million contract with the Clippers. Despite these arrangements, there is no evidence that Leonard actively promoted Aspiration, according to investigative reporting by Pablo Torre.

Allegations of Circumventing Salary Cap

An anonymous employee suggested that the endorsement deal was structured to circumvent the NBA's salary cap regulations. Torre's investigation indicated that Wong's initial investment occurred after Aspiration failed to meet its third-quarter payment obligations.

Clippers governor Steve Ballmer originally invested $50 million in Aspiration and announced a partnership worth $300 million, which included sponsorship opportunities in their new arena. However, as the situation unfolded, Aspiration filed for Chapter 11 bankruptcy on March 31, 2025.

Clippers Deny Wrongdoing Amid NBA Investigation

Following the reports, Ballmer vehemently denied any allegations of attempting to circumvent NBA regulations, stating, “These were guys who committed fraud...They conned me.” He emphasized his limited involvement in just facilitating the introduction between Leonard and Aspiration. The NBA has since confirmed the opening of an investigation into the matter, with Commissioner Adam Silver stating he had not heard of any circumvention efforts regarding Leonard and the Clippers.

This controversy echoes past inquiries into the Clippers, including a 2020 investigation regarding potential recruitment violations involving Leonard during free agency. Ultimately, the league found no basis for the allegations.