More details surface in Clippers’ Kawhi Leonard-Aspiration mess

The Clippers keep saying there’s “nothing unusual or untoward” about Kawhi Leonard’s $28 million endorsement deal with Aspiration. The problem is, every new report seems to suggest otherwise.

John Karalis of Boston Sports Journal writes that Leonard had a second deal on the side — $20 million worth of company stock — in addition to the original $28 million agreement. That alone raises eyebrows, but the way the deal was done may be even more telling.

According to Karalis, co-founder Andrei Cherny didn’t even run the contract by Aspiration’s board of directors. He signed it “as is,” against the wishes of the company’s management, who thought it was a poor use of resources and saw “no brand synergy” with Leonard.

Translation: they didn’t see what Leonard had to do with tree-planting, and never planned to use him for marketing.

Meanwhile, Clippers owner Steve Ballmer invested $50 million into the same company, reportedly doing “light-to-no diligence” and even paying more per share than Oak Tree Capital Management.

Typically, big-name investors get a discount for the PR boost. Ballmer went the other way, paying a premium.

Rival execs are not buying the Clippers’ explanations. One general manager told The Athletic’s Sam Amick, “This sort of endorsement deal does not happen.”

Another told Chris Mannix of Sports Illustrated that if things are as they appear, “Adam (Silver) has to make an example of them.”

The league has already opened an investigation. What remains unclear is whether this winds up as nothing more than messy optics — or if the Clippers get hit with something closer to the Timberwolves’ infamous Joe Smith penalty from two decades ago.

For now, it’s worth noting Leonard himself hasn’t been accused of doing anything improper. The focus is squarely on the structure of the deal and Ballmer’s investment, and whether the NBA views it as a blatant attempt to skirt the cap.

Pablo Torre was the first to raise those questions with his original reporting, and the league’s investigation is now playing catch-up.