Former Aspiration CEO Pushes Back Against ‘No-Show’ Claims in Kawhi Leonard Deal

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Written by William

September 14, 2025

Andrei Cherny, who ran Aspiration until 2022, fired back at critics Friday over accusations that Kawhi Leonard’s endorsement contract was essentially free money with no strings attached.

Contract Had Real Teeth, Former CEO Insists

Taking to X to set the record straight, Cherny wasn’t having any of the “no-show” narrative. The deal came with three pages of detailed requirements that Leonard needed to hit, and Aspiration could pull the plug if he didn’t deliver.

Cherny also tackled what he called a misunderstood “beliefs” clause—something he says is pretty standard stuff in celebrity deals. Think of it as protection against forcing someone to do something that goes against their core values. A vegetarian spokesperson shouldn’t have to chow down on a burger for a campaign. But this clause? It didn’t give Leonard a free pass to skip media duties.

No Salary Cap Talk, But Plans Were in Motion

The former executive was clear on one point: he doesn’t remember any chatter about NBA salary cap implications when they hammered out Leonard’s deal. What he does recall are internal conversations about rolling out Leonard-centered initiatives during the 2022-23 season—plans that were brewing before Cherny left the company.

Of course, he can’t speak to what happened after his departure. That’s someone else’s story to tell.

The Spark That Lit This Fire

All this drama stems from reporter Pablo Torre’s bombshell about a supposed four-year, $28 million endorsement package between Leonard and Aspiration. Critics jumped all over it, calling it a sweetheart deal designed to skirt NBA rules. The connection? Steve Ballmer, who owns both a stake in Aspiration and the entire Los Angeles Clippers organization.

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Torre wasn’t backing down from Cherny’s pushback, claiming he’d tried multiple times to get the former CEO on the record. Emails apparently got buried in spam folders—a digital age classic. Torre even shared a screenshot connecting Cherny to fraud allegations that surfaced during his 2024 congressional run in Arizona.

Cherny shot back, saying those earlier reports got it wrong and that legal proceedings had already identified the real culprit.

Clippers Distance Themselves

The Clippers organization moved quickly to distance itself from any wrongdoing. Their official statement rejected any suggestion of intentional salary cap violations and revealed they’d already cut ties with Aspiration during the 2022-23 season when the company failed to meet its contractual obligations.

Team officials say neither the franchise nor Ballmer knew about any potential misconduct until federal investigators started digging. They’ve pledged full cooperation with authorities.

League Brings in Heavy Hitters

The NBA isn’t taking this lightly. League officials have launched their own investigation and brought in Wachtell, Lipton, Rosen & Katz—the same legal powerhouse that handled the Donald Sterling mess and the Robert Sarver situation.

When the NBA calls in Wachtell, you know they’re not messing around. This firm has become the league’s go-to for handling its biggest scandals and most sensitive investigations.

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William is a proud Chicago native who’s passionate about the city, its culture, and everything happening in it, especially sports. With a background in journalism and a deep love for the Bears, he covers stories with insight, energy, and a local’s perspective.

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