The Richest Owner, the Silent Superstar, and the Rotten Apple Tree: A PTFO Investigation

EPISODE 273: Our partnership begins.

This is a very special episode of Pablo Torre Finds Out.

And not just because it’s an exclusive investigation. (Which took seven months.)

Involving 3,487 pages of internal corporate documents I obtained. (We counted.)

Also: Iron Man, Martin Luther King, and Bill Clinton are in here. (Seriously.)

This is a very special episode because it marks the start of a new partnership.

Which, to reiterate, does not mean that we’re making this show any differently. (As you’ll see.) To be completely clear: Pablo Torre Finds Out is independently produced by Meadowlark Media and distributed by The Athletic. The views, research, and reporting expressed in this episode are solely those of PTFO — and do not reflect the work or editorial input of The Athletic or its journalists.

This means that PTFO will stay free.

And that we’re gonna keep trying to come up with stuff like this:

My firm recommendation today is that you experience this the way former Marlins president David Samson and former Suns executive Amin Elhassan experienced it: by sitting down without knowing what the hell is even going on.

But.

Because this is a mystery box that’s likely to make some news, we’ve also prepared a dispassionate summary for anyone looking to pull basic facts… below.

SPOILER ALERT (UNLESS YOU’RE A MEDIA OUTLET OR AGGREGATOR):

May this large vertical image be a sufficient exit ramp to scroll past the below.

September 3, 2025

Kawhi Leonard ‘no-show’ endorsement deal linked to Steve Ballmer investment: ‘It was to circumvent the salary cap’

NEW YORK (PTFO) — Los Angeles Clippers superstar Kawhi Leonard signed a $28 million endorsement deal with an environmental startup funded by Clippers owner Steve Ballmer, according to an investigation by “Pablo Torre Finds Out.” Former employees are now raising concerns that Ballmer’s $50 million personal investment in the company — currently under federal investigation for fraud — went on “a round trip” to power Leonard’s “no-show job” and skirt NBA rules.

Torre obtained more than 3,000 pages of documents from inside Aspiration — a so-called “green bank” that promised to supply carbon credits and plant trees to offset the emissions of its clients. Aspiration relied on public endorsements from the likes of Leonardo DiCaprio, Robert Downey Jr. and Drake en route to a $2.3 billion valuation in 2021, when Ballmer invested and announced Aspiration as the Clippers’ founding partner to help make the team’s new Intuit Dome “the most sustainable arena in the world.”

But the company’s most expensive celebrity endorsement, by far, was never made public.

A former Aspiration employee, who worked in the company’s finance department and requested anonymity due to multiple federal investigations into the company, recalled to Torre: “We went through a litany of really, really top-tier name contracts. And then, ‘Oh, by the way, we also have a marketing deal with Kawhi Leonard’ — and that if I had any questions about it, essentially don’t, because it was to circumvent the salary cap.”

The language of Leonard’s signed endorsement contract, which was obtained by Torre, raised eyebrows inside Aspiration: It gave him “the exclusive right to control and approve all content and distribution.” And it gave Aspiration the right to terminate the contract “if Leonard is no longer an employee of the [Clippers] for any reason.”

In a statement sent to Torre’s show Tuesday on behalf of the team and its owner, the Clippers said: “Neither Mr. Ballmer nor the Clippers circumvented the salary cap or engaged in any misconduct related to Aspiration. Any contrary assertion is provably false.”

Multiple former employees independently characterized Leonard’s arrangement as a “no-show job”; none of the employees — nor Torre — found any evidence of social-media posts, photographs or appearances promoting Aspiration, as stipulated in the deal.

“He didn’t have to do anything,” the former finance department employee said.

Leonard’s agent did not respond to multiple requests for comment, including a detailed list of questions.

According to The Athletic, the NBA conducted a formal investigation of the Clippers in 2019, following complaints that Leonard’s uncle, Dennis Robertson, had requested “improper benefits” — including guaranteed endorsement money that would break the league’s collective-bargaining agreement — during the free agency process that saw Leonard sign with Los Angeles. Sources told The Athletic’s Sam Amick at the time that no evidence was found indicating that the Clippers had granted any of the requests but that the league would re-open its investigation should relevant evidence surface in the future.

A more complex timeline emerges from two years later, according to internal emails, bank statements, contracts and pitch decks obtained over the last seven months by Torre, in addition to interviews with seven former Aspiration employees:

• August 12, 2021: Clippers announce Leonard’s four-year, $176.3 million contract extension. (According to The Ringer: “This middle path surprised many NBA insiders, who had anticipated that Leonard, after declining his player option for next season, would either go short or go long on his next deal.”)

• September 14, 2021: Ballmer’s personal LLC agrees to wire $50 million investment in Aspiration, according to internal emails and a signed contract.

• September 27, 2021: Clippers announce Aspiration’s 23-year, $300 million partnership, with sponsorship plans for the team’s jersey patch and throughout Intuit Dome. (“There is a responsibility associated with building the best arena in the world,” Ballmer says in a statement.)

• October 27, 2021: Aspiration co-founder Joe Sanberg defends internal criticism. (“What you’re implying is that Ballmer’s investment was a sweetener and impure,” Sanberg emails a business partner.)

• November 22, 2021: Leonard registers company “KL2 ASPIRE LLC” with the state of California.

• April 1, 2022: Leonard’s four-year, $28 million endorsement deal with Aspiration to take effect.

By 2022, according to financial documents and the seven former employees, Aspiration was traveling quickly down the road toward bankruptcy.

Even as Aspiration’s business collapsed, said the former employee in the finance department, “Uncle Dennis demanded payment. It was priority one. It was something that had to be done, and it was crucial to our relationships with Ballmer and the Clippers.”

Robertson, who was listed as Leonard’s “designated representative” on the signed contract, did not respond to multiple requests for comment.

Echoing concerns from what multiple former Aspiration colleagues alleged could constitute “a round trip” for Ballmer’s investment, the finance department employee continued: “Why is Steve Ballmer backing a huge, historic raise for Aspiration? Like, why? Also: What was the main motivation for such a large raise? Because from inside Aspiration, we see like the glitz and the glam of the celebrities that are posting, but from the finance side, accounts receivable were wild. Like, the actual amount of money that needed to be coming in, in order for our revenue to count towards real revenue, was astronomical in comparison to what was actually being received.”

The Clippers’ statement to Torre’s show continued: “The team ended its relationship with Aspiration years ago, during the 2022-23 season, when Aspiration defaulted on its obligations. Neither the Clippers nor Mr. Ballmer was aware of any improper activity by Aspiration or its co-founder until after the government instituted its investigation. The team and Mr. Ballmer stand ready to assist law enforcement in any way they can.”

Sanberg, the Aspiration co-founder, declined to comment through an attorney. He pled guilty two weeks ago to defrauding investors of more than $248 million. “This is a case about greed and abuse of trust,” an FBI assistant director said of the charges. The Securities and Exchange Commission announced parallel charges: “The SEC’s investigation is ongoing.”

This summary, by the way, leaves out like a dozen other things I made sure to report in the show — many of which involve the Democratic Party.

And the (other) co-founder whose autograph, on a key document, abuts Kawhi’s.

Apple Time, Apple Time,

Pablo

P.S. I’m gonna do a video chat that’s for Paid Subscribers, only, this month. Think of it like a closed-door shareholder meeting, of sorts, where I’ll get into our how sausage is made. Which people (understandably) have questions about. Date TBD!

P.P.S. There will be a lot to talk about.