Clippers co-owner Dennis Wong reportedly invested $1.99 million to a failing Aspiration days before Kawhi Leonard payment

The Los Angeles Clippers and owner Steve Ballmer are already under investigation by the NBA after a report emerged suggesting the team and Ballmer supplied impermissible benefits to superstar Kawhi Leonard to try and circumvent the salary cap. Both the Clippers and Ballmer vehemently denied those reports, claiming they did not funnel money to Leonard through Aspiration, a company in which Ballmer invested.

Those denials were called into question Thursday thanks to new reporting by journalist Pablo Torre. On the latest episode of Torre's podcast — Pablo Torre Finds Out — he detailed a surprising investment by Clippers co-owner Dennis Wong into Aspiration that may have been used to pay Leonard.

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Torre, who broke the original story, once again uncovered legal documents that show Wong — Ballmer's former college roommate — invested $1.99 million in Aspiration through a company called DEA 88 Investments just nine days before Leonard received a $1.75 million payment from the company.

The investment from Wong came while Aspiration was in the midst of serious cash-flow troubles and was already late on one quarterly payment to Leonard. Torre spoke with two former members of Aspiration who detailed the company's financial struggles at the time of Wong's investment. Torre's first source claimed Aspiration was "broke" at the time Wong made the investment in December 2022.

Torre made the argument that, at that point, Wong should have known Aspiration was failing due to Ballmer's involvement, the company letting go of key members of staff and the fact that Wong's daughter worked for Aspiration.

Despite that, Wong decided to invest an amount of money close to what Leonard was set to be paid just days before his company — KL2 Aspire LLC — received its payment. One of Torre's sources pointed out that, given the financial hardship the company was facing, a $2 million investment at that point wasn't nearly enough to save the company, casting more suspicion on the amount Wong gave to Aspiration as it was going under. Aspiration filed for bankruptcy in March.

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Torre's second source, who worked in the finance department at Aspiration, said they believed Wong put that money in to ensure Leonard got paid.

"It really looks like the Clippers, through Dennis Wong, put in $2 million in order for Aspiration to be able to make the $1.75 million payment to Kawhi. That's what it looks like, to me."

It should be noted that Torre's second source was not confirming that's what happened, but speculating based on evidence they perceived while working in the finance department at Aspiration.

On Wednesday, NBA commissioner Adam Silver spoke with reporters about the situation, and said he would need definitive evidence the Clippers broke the rule to punish the team.

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Throughout Thursday's show, Torre attempts to make the argument that Wong's investment, and Aspiration's subsequent payment, could be the smoking gun the NBA is looking for in its investigation.

If the league determines the Clippers' owners knowingly gave Leonard improper benefits after he signed with the team in free agency, the team, Ballmer, Wong and potentially many others could face harsh punishment from Silver and the NBA.

When Silver originally investigated Leonard's free agency in 2019, the commissioner said the act of giving a player impermissible benefits to circumvent the salary cap was "a cardinal sin of the NBA." The league found no evidence Leonard was given illegal benefits back in 2019.

Torre's reporting called into question whether the NBA got it right the first time around. Following Torre's second revelation, the league has even more evidence to consider after re-opening its investigation.