Steve Ballmer Made Nearly $10 Million Follow-On Investment in Aspiration, Firm at Center of Kawhi Leonard Probe
The Clippers owner invested again in the fintech firm that prosecutors say defrauded investors; the NBA is investigating whether a purported no-show endorsement for Leonard violated salary-cap rules.
Los Angeles Clippers owner Steve Ballmer made a nearly $10 million investment in fintech company Aspiration in March 2023, The Athletic reported Friday, a follow-on commitment to a firm now at the center of an NBA investigation into an alleged no-show endorsement paid to Clippers forward Kawhi Leonard.
The March 2023 infusion came after Ballmer previously committed to Aspiration in 2021 and followed a series of transactions that have drawn scrutiny from league investigators and federal prosecutors. Pablo Torre first reported on Sept. 3 that Leonard was the recipient of an alleged four-year, $28 million endorsement arrangement with Aspiration that the NBA is probing to determine whether it was used to circumvent salary-cap rules.
According to reporting by The Athletic, Ballmer’s additional investment arrived at a time when Aspiration was seeking funding. The company's financial strain is also reflected in reports that Aspiration made a roughly $1.75 million payment to Leonard soon after a nearly $2 million investment from Dennis Wong, the Clippers’ vice chairman. Wong’s reported $1.99 million investment preceded Ballmer’s capital infusion by only a few months.
Aspiration had previously signed a sponsorship deal with the Clippers worth more than $300 million that made the company a founding sponsor of the team’s new arena. The Athletic and other outlets have connected those commercial ties, Aspiration’s payments and Ballmer’s investments to the league’s inquiry into whether any side deals were used to provide Leonard compensation outside of the salary-cap framework.
Commissioner Adam Silver said Wednesday that the league intends to investigate but emphasized that punishment would require solid evidence. "I would be reluctant to act if there was a mere appearance of impropriety. I think the goal of a full investigation is to find if there really was impropriety," Silver said. He added that public conclusions can be premature and stressed the need for fairness to everyone under scrutiny, including Ballmer and Leonard.
Ballmer has publicly addressed his ties to the company as prosecutors closed in on its management. On SportsCenter last week, Ballmer said he was "conned" by Aspiration and that his staff had reviewed what he called fraudulent financials. "These were guys who committed fraud. Look, they conned me. They conned me," Ballmer said, adding that he felt "embarrassed" for not having detected the misconduct earlier.
Federal prosecutors announced in August that Aspiration co-founder Joe Sanberg pleaded guilty to two counts of wire fraud related to a scheme that defrauded investors and lenders of more than $248 million. The Justice Department’s announcement and subsequent reporting have heightened questions about the firm’s transactions and whether some payments to high-profile athletes might have been structured to conceal compensation.
Investigators are examining whether any endorsement payments were bona fide compensation for services or whether they were effectively no-show deals intended to augment player pay without being counted against salary-cap calculations. Torre’s reporting said the alleged Leonard deal was a four-year contract totaling about $28 million; Aspiration’s efforts to meet contractual obligations reportedly became strained as the company experienced liquidity issues.
The NBA’s probe into possible salary-cap circumvention will consider the timing and nature of Aspiration’s commercial relationship with the Clippers, the timing of investments from team-affiliated individuals and the pattern of payments to Leonard. Silver’s comments indicate the league is seeking documentary evidence that would establish intent or coordination to violate the collective bargaining agreement.
Aspiration’s sponsorship agreement with the Clippers and Ballmer’s prior, larger commitment to the company have generated particular interest because team owners and their businesses are subject to league rules intended to prevent circumvention of roster and financial regulations. Ballmer’s initial reported investment in the company occurred after Aspiration became a major commercial partner of the team, and the later March 2023 infusion came as the company sought additional capital.
Legal filings and plea agreements tied to the Aspiration case could produce documents relevant to the NBA’s inquiry. The league’s investigation is focused on determining whether evidence shows an attempt to evade salary-cap accounting; Silver said the league would be guided by facts rather than appearances. Any findings of impropriety could lead to penalties under the collective bargaining agreement, but Silver cautioned that investigations must establish wrongdoing before sanctions are considered.
Ballmer’s public comments acknowledging he invested in a company whose executives committed fraud point to potential civil and financial implications for investors and commercial partners. Aspiration’s legal and financial troubles, the federal guilty plea, and the NBA’s separate regulatory review together create a complex set of inquiries that will determine whether commercial arrangements, investments and payments violated legal or league standards.
The Athletic and Pablo Torre’s reporting provided details about the timing and amounts of the investments and payments; prosecutors’ filings and Ballmer’s statements have confirmed some elements of the broader fraud case. The NBA has not announced a timetable for concluding its probe, and Ballmer and the Clippers have declined further comment beyond public statements referenced in reporting.
Investigators will weigh transactional records, communications among company executives and team officials, and contemporaneous documentation of endorsement agreements to determine whether compensation to Leonard or others was legitimate or a vehicle for circumvention. The outcomes of the federal case against Aspiration executives and the NBA’s separate regulatory process may unfold on different timelines but could intersect if court evidence sheds light on alleged conduct affecting league rules.