Kawhi Leonard Was Owed $1.75 Million From Aspiration; Clippers Co-Owner Then Invested $1.99 Million And The Claw Got Paid

The ongoing Kawhi Leonard–Aspiration saga has taken yet another dramatic turn, this time involving a Clippers co-owner’s money and a payment that Leonard reportedly received while the company was crumbling. 

Pablo Torre’s latest episode of Pablo Torre Finds Out revealed that Aspiration, the “green bank” that had signed Leonard to a lucrative endorsement deal, wired him $1.75 million on December 15, 2022. That payment came the very same day the company laid off 20 percent of its staff.

The twist? Just nine days earlier, Clippers minority owner Dennis J. Wong had invested nearly $2 million into the failing company. According to Torre’s reporting, bank records showed a $1,999,999.59 wire from Wong’s DEA88 Investments on December 6. Less than two weeks later, Leonard’s quarterly payment went through, even as Aspiration was hemorrhaging cash.

Former Aspiration employees interviewed on Torre’s podcast were stunned. 

“It is beyond shocking. To invest in a broke company is baffling. And then to see $2 million come in and $1.75 million go out to Kawhi… it makes no sense as a rational investment.” 

Another employee noted that while employees were panicking about whether they’d even get their own paychecks, Leonard’s deal was treated as “critical.” 

As one put it bluntly: 

“But lo and behold, Uncle Dennis gets paid.”

Leonard’s contract with Aspiration, originally worth $28 million over four years had already raised eyebrows. It stipulated quarterly payments of $1.75 million but gave Leonard the right to decline any promotional obligations he didn’t like. 

On top of that, Leonard reportedly received $20 million in stock from Aspiration’s co-founder, Joe Sanberg. This was all while Aspiration was also signed as the Clippers’ jersey sponsor in a $300 million deal.

The NBA is now investigating whether Leonard’s endorsement deal with Aspiration amounted to cap circumvention essentially, if the Clippers found a way to funnel extra compensation to their star forward outside of his league-approved contract. League rules prohibit such arrangements, and if proven, the punishment could be severe: forfeited draft picks, fines, or even voiding Leonard’s contract.

Clippers majority owner Steve Ballmer, who himself invested $50 million into Aspiration in 2021, has denied wrongdoing. He has claimed he was defrauded by Sanberg, who has since pleaded guilty to federal fraud charges. 

Wong, meanwhile, has largely stayed out of the public spotlight, but his December 2022 transfer is now at the center of questions about whether Leonard’s payments were indirectly subsidized by team ownership.

For Leonard, the optics are messy. His uncle and longtime business manager, Dennis Robertson, often referred to as “Uncle Dennis,” had reportedly been making persistent calls to Aspiration over late payments. Employees described feeling hounded by Robertson’s demands while they were watching their own jobs disappear.

The NBA is treading carefully, with commissioner Adam Silver stressing that the league needs “clear evidence” before taking action. Still, insiders believe this latest revelation money in from a Clippers owner, money out to Leonard days later, may be the smoking gun the league was looking for.

For now, the saga continues, casting a cloud over Leonard, the Clippers, and what was once billed as a forward-thinking partnership between a star, his team, and a “green bank” that is now bankrupt. If the NBA rules this was a hidden form of salary, it could go down as one of the league’s biggest scandals in years.