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LAS VEGAS — As Kawhi Leonard watched a Toronto Raptors game courtside at Thomas & Mack Arena Monday night, he sat several seats down from the franchise’s general manager and its former governor. He is a former Raptors star and seemingly a future one, but for now he remains in limbo. As the NBA’s probe into Leonard’s no-work sponsorship deal with a formerly little-known environmental company enters its 11th month, it has brought the player and team in the middle of it to a standstill.

While the LA Clippers, Leonard and now the Raptors all wait for a conclusion, the investigation has grown in scope since it began, according to multiple sources who spoke to The Athletic on the condition of anonymity in order to speak freely. Not only has Wachtell Lipton, the league’s go-to law firm hired to conduct the inquiry, inspected if the Clippers circumvented the NBA salary cap by facilitating a sponsorship deal for Leonard with Aspiration, it has also looked into whether the Clippers improperly covered expenses for Leonard but were not reimbursed for them, those sources said. And the firm has examined if Leonard had a previously unreported endorsement deal with another company, those sources said.

The investigation has been a source of intrigue and frustration around the NBA this season. Last week, Toronto paused a trade to bring Leonard back after the league informed the Raptors they would bear the risk of any punishment resulting from the investigation if they acquire Leonard. While a team source denied that the delay is an implication that Toronto fears or expects some penalty, it does show how the probe is already creating consequences even as it continues to examine possible cap circumvention by the Clippers.

Although NBA commissioner Adam Silver said last month that he hoped the investigation would wrap up soon, he could offer some answers at his Board of Governors news conference Tuesday but the league has offered no inkling of where the investigation is headed. Some team executives around the league have increasingly come to expect that the league will punish the Clippers.

The Clippers and owner Steve Ballmer have vehemently denied any wrongdoing. Ballmer has said he was the victim of fraud and one of many who lost money in a company that went bankrupt and saw its co-founder plead guilty to federal fraud charges.

“W​​e don’t think that there’s a ‘there’ there,” National Basketball Players Association executive director David Kelly said. “It should not take this long in order for something to get wrapped up.”

The origin of the investigation remains Leonard’s contract with Aspiration, for which he was to be paid $28 million until the company ran into financial issues and ultimately filed for bankruptcy. Leonard never publicly promoted the company. The “Pablo Torre Finds Out” podcast was the first to report its existence in September. As the NBA tries to wrap up its investigation, former Aspiration employees — who have spoken anonymously with The Athletic over the last 10 months to ensure their candor during an open investigation — still do not know definitively if the deal was intended to bypass the cap, though they have their opinions.

Several believe only Aspiration co-founder Joe Sanberg knows for certain. Some say that Aspiration made authentic attempts to market Leonard but failed, in part, because the NBA star was such a poor choice as a spokesman. This spring, Sanberg was sentenced to 14 years in federal prison after he pleaded guilty to two counts of wire fraud, but has spoken to the NBA’s investigators.

Others have come to believe that cap circumvention was at play.

“The conclusions that people seem to be drawing don’t seem unreasonable to me,” one former high-ranking executive said. “No person knowledgeable about the Aspiration customer would think it was a good idea to invest in Kawhi Leonard that amount of money.”

The Clippers, a representative for Leonard and an attorney for Sanberg did not respond to questions and requests for comment from The Athletic by publication time. The NBA declined to comment for this story.

Key questions remain, including why Aspiration signed Leonard to a lucrative sponsorship deal in the spring of 2022 in the first place. Leonard’s contract gave him broad discretion to deny work for the company and he did not appear in any public marketing campaigns for Aspiration.

Leonard’s deal became a point of confusion for Aspiration executives who spoke to The Athletic. They did not see Leonard as a natural spokesman for the company because of his detached public profile, limited social media presence and what they believed was a lack of fit to market the product.

Aspiration did discuss using Leonard in a marketing campaign, multiple former employees told The Athletic. Executives exchanged emails with members of the Creative Artists Agency on potential concepts. And members of Aspiration’s marketing department were told they could use Leonard to promote the company and to try to find a way to do so, one person with knowledge of Aspiration’s marketing strategy said.

Leonard was, that person said, difficult to build a campaign around. Despite his basketball accomplishments, his wider public profile was small and, in the eyes of Aspiration’s marketing employees, he lacked the notoriety of other NBA stars. That made the naturally introverted Leonard a difficult muse. Some in the department heard that Leonard was into comic books and superheroes, so that was floated as a concept. The efforts went so far as to create images, reviewed by The Athletic, of Leonard as an offshoot of Marvel’s Groot – Aspiration’s purpose was a promise to plant trees to offset carbon footprints.

But after weeks of trying to work with the Marvel concept and brainstorm other ideas, the creative team was told to quit, according to multiple former Aspiration marketing employees.

“Stop thinking about Kawhi,” the person said they were told. “This feels like a dead end.”

The team had been unable to come up with anything worth pursuing.

“Nothing ever came from it,” another former Aspiration employee said. “I’m not sure why it died, whether it was on our end or his end or if we couldn’t figure out a concept.”

Despite the inactivity, Leonard and the Clippers were considered a vital part of Aspiration’s portfolio. The team and its star were priorities for the company, those people said, though their understanding of the reasons differ.

One person recalls Sanberg saying that the Leonard deal came with an understanding the team and the company would work on more deals together, and that the two were linked, though not as an explicit quid pro quo. The Clippers, this former executive said, wanted Aspiration to do the deal with Leonard.

“I didn’t think of it so much as a quid pro quo but as a ‘you scratch my back, I scratch yours,’” the person explained. “I know there’s a fine line but it doesn’t seem one was tied to the other.”

Another former executive disputed the notion that the Leonard deal was seen as a way to ensure more business with the Clippers. “Paying Kawhi was important,” they said, but so were the relationships with the franchise and Ballmer in general. The Clippers relationship was understood to be a high priority.

Former Aspiration CEO Andrei Cherny signed off on the contract with Leonard, though Sanberg brought the Clippers star in, multiple sources said. The sponsorship deal, sources said, was worth significantly more than the endorsement deals Aspiration reached with the musician Drake, who invested $4 million and received carbon credits, and actor Robert Downey Jr., who received less than $2 million in equity. Sanberg also gave Leonard $20 million in equity in the company, The Athletic reported in September.

“It was viewed as a sinkhole,” a former C-suite member of Aspiration said.

Sanberg approved other small gratuities to Leonard. He agreed that Aspiration would pay Leonard’s $17,181 in legal fees associated with the deal, according to emails reviewed by The Athletic, after a conversation with Dennis Robertson – Leonard’s uncle and business adviser.

When the company’s top lawyer refused to pay after the deal closed because it veered from business norms, Leonard’s then-agent Mitch Frankel emailed Sanberg directly, and reminded him of the agreement with Robertson. The company ultimately agreed to pay, though the lawyer emailed Frankel that “Aspiration was unaware of the arrangement Joe made” but said he wanted a “great relationship” with Leonard.

“It’s false that Aspiration was unaware of the arrangement,” Sanberg responded in an email, with his two lawyers read in. “I verbally informed Aspiration’s CEO of the legal fee reimbursement part of the deal when I agreed that the Aspiration stock that Kawhi would get would be from my personal stock rather than the company.”

Sanberg could be, according to people who know him, capricious and occasionally hot-headed.

“You didn’t know which version of him you were going to get,” said one person who did business with Sanberg and did not work at Aspiration. Sanberg, he added, “was combustible.” Aspiration employees were not spared.

Sanberg, former employees said, could often act imperiously. They sometimes scrambled to catch up.

Sanberg, according to former Aspiration executives, was one of the few who knew how the deal originated. While he was not an executive, he was a board member who wielded influence inside Aspiration.

The deal with the Clippers and a relationship with Ballmer was driven by Sanberg, sources said. Ballmer had “a great relationship with Joe,” one former Aspiration executive said, beyond just sharing a dais together during a 2021 news conference that announced Aspiration as a jersey patch partner for the Clippers.

The Ballmer Group, the philanthropic organization the former Microsoft CEO ran with his wife, had made grants to Sanberg’s foundation, Golden State Opportunity, for years. The first was for $500,000 in 2017, GSO president Amy Everitt said, then a $1 million grant that was appropriated over two payments beginning in May 2019, a $1.5 million grant in 2021, and, finally, as first reported by “The Pablo Torre Finds Out podcast,” a $1.875 million grant in 2024.

By the time of the last grant, Ballmer had already put $60 million into Aspiration and the company had burned through most of it. The company had dropped into a free fall a year earlier, when it was hemorrhaging money and laying off employees. Ballmer made a second investment in March 2023 for $10 million but it did not stabilize Aspiration. But the company kept paying Leonard. Aspiration was also a key partner for the Clippers as it launched the Intuit Dome in 2021 and its jersey sponsorship deal was worth more than $300 million. The Clippers also paid Aspiration for carbon credits, sources said.

Ballmer has repeatedly denied that he did anything wrong, as have the Clippers.

“We did not funnel money to Kawhi Leonard through Aspiration,” the Clippers said in a statement last week. “Like many sophisticated investors, financial institutions, and business partners, we were victims of a fraud initiated by Sanberg… We remain confident that, when the facts are evaluated fairly and thoroughly, the NBA will confirm exactly what we have said from the beginning: We have not done what we are accused of doing.”

The closest Ballmer has come to a full accounting was in a letter this spring to the federal judge who oversaw Sanberg’s sentencing after he pleaded guilty to fraud charges. Federal prosecutors said that, beginning in 2020, Sanberg stole $6.65 million from investors and that he caused $248 million in total losses for those he had defrauded. He has been sued in New York state court by lenders who say that he took out $145 million in loans under false pretenses, and the SEC has accused Sanberg of falsifying tens of million dollars in revenue for Aspiration to lure in investors. The letter, written by Ballmer’s lawyer, said Ballmer had incurred reputational damage as a result of Sanberg and asked the judge to “impose a sentence that accounts for those harms.”

It is not clear what Sanberg knows or what his motive might have been to bring Leonard in as an Aspiration endorser. Sanberg spoke to Wachtell as part of its investigation, its lead attorney, David Anders, told the judge who oversaw his federal case. Anders said that Sanberg had given them information that was “consistent with our review of contemporaneous documents and other evidence” and that he had “substantially” helped their work.

David N. Kelley, Ballmer’s attorney, however, told the judge that Sanberg had ignored their attempts to speak and believed the “reliability of Sanberg’s information is suspect.” Other former high-ranking Aspiration executives have also spoken with Wachtell lawyers as part of the investigation, sources briefed on the investigation confirmed. Leonard and his uncle, Robertson, have also been interviewed, sources said. ESPN was the first to report that the star and his uncle had interviews, along with Ballmer.

What Sanberg told Wachtell investigators could go a long way in trying to understand how the Leonard deal came together. Though, as the NBA now examines if Leonard had another endorsement deal, his may not be the only company that matters.

Even after the investigation ends, the path forward may not be simple. The NBA will need an arbitrator designated by the NBPA and the league to rule that a violation of the collective bargaining agreement has occurred. The NBA could avoid that route if it reaches a settlement with the team and Ballmer.

For now, questions remain as the NBA and Wachtell complete their work, and the rest of the league waits for answers.