The Clippers’ Aspiration scandal is deeper than it looks, and the money trail is finally coming into focus. In March 2025, Aspiration filed for bankruptcy after years of missed payments, federal probes, and mounting lawsuits. By then, it had already fallen behind on a four-year, $28 million endorsement deal with Leonard, a contract that required little in the way of promotional work and raised questions about how the struggling company was able to keep paying him. The NBA has since launched an independent investigation to determine whether the Clippers or their ownership group played a role in propping up those payments.

Until recently, most of the scrutiny focused on Steve Ballmer, who invested $50 million in Aspiration back in 2021 and introduced the company to Leonard later that year. But new reporting suggests Ballmer wasn’t the only figure tied to the team with money on the line. The journalist who first broke the story, Pablo Torre, has now spoken out again with fresh revelations and analysis on the controversy.

Clippers minority owner Dennis Wong has now been pulled directly into the controversy after records showed he wired $1.99 million to Aspiration on December 6, 2022, just nine days before the company sent Leonard a $1.75 million payment that had been overdue for months. The timing alone raised questions, but the story took another turn when Pablo Torre addressed it on the LeBatard show.

“The only thing I’ve heard back channel, which makes me laugh very hard, is that Dennis Wong, who was an incredibly wealthy real estate magnate, he wanted to save his daughter’s job by putting in $2 million into a company that was valuated, by the way, still at the time of his investment,” Torre said. He emphasized that Wong made this investment even though Aspiration had already defaulted on its debts, lost its independent auditor, faced seven-figure lawsuits, and was under active probes by the SEC and FINRA.

Despite all of these red flags, Wong’s firm DEA 88 Investments still put in nearly $2 million at a valuation of more than $2 billion. “So why did he still do it?” Torre asked, pointing out that Wong had full access to paperwork disclosing Aspiration’s financial troubles.

One back-channel theory Torre heard was that Wong was trying to save his daughter’s job at Aspiration by injecting money into the failing firm. But he quickly dismissed that idea as “insanely nonsensical.” As Torre put it, “The daughter recently graduated from Stanford, the company was broken and falling apart, Dennis Wong is extraordinarily rich and doesn’t need to save his daughter’s job at a broken company that is going into the trash can.”  In his view, the investment only underscores how irrational and suspicious the financial dealings around Aspiration really were, especially when they intersected with payments to Leonard.

Torre dismissed the notion that Wong’s money was meant to secure his daughter’s position at the collapsing firm, noting that Wong’s wealth made such a move unnecessary, and that if such a payment were meant as a bribe, “that’s a different potential crime.” His conclusion was stark: Wong’s investment at a $2 billion valuation in a company already “going into the trash can” underscores just how irrational and suspicious the financial maneuvers around Aspiration had become.

For the Clippers, this broadens the probe from one owner’s aggressive investment practices into questions of whether the entire ownership group was complicit in finding creative, off-books ways to reward their superstar.

Possible punishments for Leonard, Ballmer, and now Wong

The NBA controversy surrounding the Clippers has escalated, with rival teams reportedly demanding a $149 million penalty for Steve Ballmer over alleged salary-cap circumvention. The figure aligns with Kawhi Leonard’s three-year, $149.5 million contract extension signed in January 2024, though under the league’s collective bargaining agreement, fines of this size would be unprecedented. Potential penalties for violations include multi-million-dollar fines, forfeiture of draft picks, and even voiding contracts, raising questions about whether Ballmer, Leonard, and now Dennis Wong could all face league action.

Pablo Torre highlighted Wong’s role on the same show, explaining that “Kawhi’s camp was very upset about this and it forced Wong to make this deposit, and then all of a sudden Kawhi started playing again.” Torre added that Leonard’s second-ever quarterly payment had been three months late, and Wong’s intervention directly enabled the payment, raising questions about whether the minority owner’s actions could now attract league scrutiny alongside Ballmer’s.

The implications for Leonard himself are also uncertain. Torre has noted that payments were structured through Leonard’s personal entity, KL2 Aspire, LLC, which complicates the question of intent and league rules. As the investigation continues, the NBA will need to determine whether Leonard’s representatives, Ballmer, and Wong knowingly participated in circumventing the salary cap.

Ultimately, the scenario poses a stark question: if Leonard or any member of the Clippers’ ownership group is found guilty of impropriety, what will the penalties look like, and how will it reshape the franchise’s financial and competitive future?