RealGM Basketball Wiretap

15 September 2025

• Former Aspiration CEO Defends Kawhi Leonard Deal Structure

  Internal emails revealed Aspiration executives expressed concerns about Kawhi Leonard's endorsement contract, which required minimal promotional work while allowing the Clippers star significant control over his obligations, according to documents obtained by The Athletic.

  The deal specified Leonard would participate in one eight-hour production day, one four-hour PR session, two community service events, and weekly five-minute conversations with Ty Lue during his 2021-22 injury recovery. Leonard also agreed to provide "five organic comments/likes/RTs as requested by Aspiration" and participate in three off-court projects.

  However, the contract included provisions allowing Leonard to refuse requests "not consistent with his beliefs" and gave him sign-off authority on all activities. Aspiration could terminate the agreement if Leonard was no longer playing for the Clippers or for cause.

  Aspiration marketing executives expressed frustration with the contract structure in internal communications. One executive noted the deal had "pretty big flags" and complained that Leonard's limited social media presence would "significantly hamper" the company's promotional efforts.

  The executives initially considered marketing campaigns involving Leonard alongside Drake, a celebrity client and endorser. However, they ultimately decided against using Leonard as a spokesperson, with one executive believing the famously quiet star did not fit that role.

  Andrei Cherny, Aspiration's co-founder and CEO until 2022, disputed characterizations of the Leonard deal as problematic when contacted by The Athletic. He emphasized that celebrity endorsement contracts commonly include beliefs clauses and termination options for non-performance.

  "In the months of discussion among our executives before signing the sponsorship, I don't remember conversations about the NBA salary cap," Cherny said. "I signed the contract shortly before I submitted my resignation, but before I left there were numerous internal conversations about the various things Aspiration was planning to do with Leonard once the 2022-23 season began, including emails from the marketing team about their plans in just the week before my last day."

  Three former Aspiration executives issued a joint statement responding to Cherny's comments, claiming the Leonard contract was delivered already completed without proper review. The former chief legal officer, chief technology officer, and chief financial officer said they raised concerns about the deal's cost and strategic value.

  "The team expressed concerns at the time regarding the high cost of the agreement and its lack of alignment with Aspiration's brand and business strategy," the executives stated to The Athletic. "While subsequent marketing efforts were undertaken, they were ultimately discontinued and should not be interpreted as support for the deal itself."

  The Leonard contract reportedly exceeded Aspiration's agreements with other celebrity endorsers. Leonardo DiCaprio and Robert Downey Jr. received less than $2 million in equity, while Drake invested $4 million but also received carbon offsets, according to a former executive.

  Leonard never publicly promoted Aspiration during the contract period, despite the company's initial marketing plans.

• Steve Ballmer Invested Another $10M In Aspiration In March 2023

  Steve Ballmer invested nearly $10 million into Aspiration in March 2023, which followed his initial $50 million investment 18 months earlier, according to legal filings reviewed by The Athletic and corroborated by a former executive with the company. Ballmer's $10 million investment came as Aspiration was quickly losing cash, laying off employees and struggling to raise funds.

  The March 2023 investment by Ballmer followed a December 2022 investment of $1.99 from Los Angeles Clippers minority owner Dennis Wong. Wong is Ballmer's college roommate and vice chairman of the Clippers.

  A $1.75 million payment by Aspiration was made to Kawhi Leonard shortly after Wong's investment.

  The March 2023 round of fundraising had a target of $75 million, but they came up nearly $9 million short. Nearly all of the investors had previously invested into the company.

  Leonard and the Clippers are under investigation for possible salary cap circumvention. Leonard received a no-show endorsement deal with Aspiration worth $28 million over four years. Leonard also received $20 million in stock.

  Aspiration co-founder Joe Sanberg introduced the deal to the company, but it received scrutiny from executives as they believed it held little value.

  "I am personally contributing stock to Kawhi to make this partnership possible," Sanberg wrote members of his leadership team in a May 2022 email obtained by The Athletic. "Aspiration's CEO judged the deal to be not worth doing. For avoidance of doubt, any and all benefit to Aspiration from the Kawhi deal is being subsidized by my contributing my equity to make this happen."

  Aspiration employees said that Sanberg built and maintained a relationship with Ballmer to convince him to invest in the company.

• Rival Execs Argue 'Circumstantial Evidence', Above 'Fair Market Value' Terms Implicate Clippers

  For those within the NBA who believe the Los Angeles Clippers should be punished for an alleged salary cap circumvention with Kawhi Leonard, they are citing that there is enough circumstantial evidence already established to do so, reports Jake Fischer.

  On Page 341 of the league's newest Collective Bargaining Agreement under Article XIII titled "Circumvention," punishment can be issued against a team or player if a violation of unauthorized agreements can "be proven by direct OR circumstantial evidence."

  The NBA has opened an investigation into the Clippers and while Pablo Torre's reporting has yet to find a directive from anyone associated with the team to pay Leonard via Aspiration, there is ample circumstantial evidence in the eyes of rival team executives.

  Further adding to the circumstantial evidence argument is Leonard had a "no-show" endorsement contract and numerous sources tell Fischer that the $7 million annual salary is well above "fair market value." According to Torre, the endorsement deal was above what he made in his shoe deal with New Balance.

  One agent Fischer spoke to, however, suggested that Aspiration's combination of being an illegitimate business not familiar with the sports industry, could have plausibly led them to make a bad deal directly with Leonard's camp. For example, Aspiration offered the Clippers a $300 million jersey sponsorship deal over 23 years, which was a far longer structure than any other team.

  The Clippers maintain that Dennis Robertson was the one who sought and negotiated the deal with Aspiration.

  During Adam Silver's press conference on Wednesday, he suggested that the "burden" of proof is on the NBA's investigation to prove the Clippers were directly involved in order for a punishment to be given to the franchise rather than strictly circumstantial evidence.

• Adam Silver Asked Owners To 'Withhold Judgment' On Clippers Until Investigation Wraps

  After Wednesday's NBA Board of Governors meeting, Adam Silver was asked to characterize the feedback he has received from other owners in response to allegations that the Los Angeles Clippers may have circumvented the salary cap with Kawhi Leonard's $28 million endorsement deal with Aspiration.

  Silver suggested that he limited the discussion of the topic amongst the governors as he wants to let an independent law firm, Wachtell, Lipton, Rosen & Katz,

  "At least what's being said to me is a reservation of judgment," said Silver. "I think people recognize that that's what you have a league office for. That's what you have a commissioner for, someone who is independent of the teams. On one hand, of course, I work collectively for the 30 governors. But I have an independent obligation to be the steward of the brand and the integrity of this league.

  "At least what those governors have said directly to me, to the extent we have had discussions, they've been limited. We communicated to them that we engaged Wachtell, as I said earlier, to do this investigation. And maybe I cut off any further conversations and said, let's all withhold judgment, let's do this investigation and then we will come back to you in terms of our findings."

• Kawhi Leonard Received Aspiration Payment Days After Clippers Minority Owner Investment

  Los Angeles Clippers minority owner Dennis J. Wong made a nearly $2 million investment in Aspiration in December 2022 just days before the company paid Kawhi Leonard $1.75 million as required through his endorsement contract, according to a new episode of Pablo Torre Finds Out. The payment was made on December 15th, which was the same day the company laid off 20 percent of its employees.

  "It is beyond shocking, and I will tell you, I knew that the board (of directors at Aspiration) had put (in) money in December to make payroll and make rent... (so) it is not a rational investment that someone (Wong) would make," one of two anonymous former Aspiration employees said on the podcast. "So it is very shocking to me that $2 million was made as an investment by Dennis Wong, who in my texts is identified as... Steve Ballmer's partner a week before $1.75 million was paid to Kawhi."

  "There's multiple things that are conspicuous," said a second anonymous former Aspiration official. "One, we're broke. We're broke. So to invest in a broke company is beyond me.... And then the other thing is the amount that's being invested, that's such a nominal amount if we're talking pure investment, especially in a late-stage startup that's... already raised a year earlier $300 million (sic), what does $2 million buy you?"

  According to Torre, Wong made a a confidential stock purchase agreement from Aspiration dated Dec. 9, 2022, in which his limited partnership DEA 88 Investments bought 0.072 percent of the environmental firm.

  "In all fairness to Uncle Dennis (Robertson), he's not the only one who's calling trying to get paid," one of the former Aspiration employees said on the podcast. "There's a huge freeze because there's no money to be spent. So from the finance team's perspective, we feel like we're on the other end of collections calls. People are constantly coming in asking for their money.

  "Between those months when all of this is missing - so September, October, November, and leading up to December, the actual certainty of the company even existing is up for grabs. At that point, are we gonna get paid as employees? Why does Uncle Dennis keep calling us? We have such bigger concerns that we're thinking about, which is our own salaries. Are we gonna have to go through layoffs? Where is the money gonna come from?

  "But lo and behold. Uncle Dennis gets paid."

  Adam Silver weighed in on the NBA's investigation into possible salary cap circumvention committed by the Clippers and said the "burden" is on the league to prove the team actually committed wrongdoing in order for them to be punished.

• Kawhi Leonard's Camp Asked Lakers For Endorsement Promise Without No-Show Clause

  Dennis Robertson, uncle of Kawhi Leonard, did not request a no-show endorsement deal with the Los Angeles Lakers during their 2019 free agency discussions, sources tell Sam Amick of The Athletic. However, Robertson did ask for a specific amount of off-court endorsement compensation that could be promised in advance of Leonard signing with the Lakers.

  According to a report from Bruce Arthur of The Toronto Star, Robertson asked the Toronto Raptors for at least $10 million per year in additional no-show sponsorship income.

  The Los Angeles Clippers are under investigation following Pablo Torre's report that Leonard had a $7 million per year no-show endorsement deal with team sponsor Aspiration.

• Adam Silver Confirms 'Burden' Of Proof On NBA In Kawhi Leonard Probe

  NBA Commissioner Adam Silver emphasized the league bears the burden of proof in its investigation of the Los Angeles Clippers' potential salary cap circumvention involving Kawhi Leonard's $28 million Aspiration endorsement deal. Aspiration had a $300 million sponsorship deal with the Clippers and touted Steve Ballmer as an investor.

  The commissioner made clear that fundamental fairness requires the NBA to prove any wrongdoing rather than forcing teams or players to prove their innocence. Silver confirmed an external investigation is underway while outlining the league's extensive disciplinary powers.

  Silver stressed the importance of placing investigative burden on the accusing party. The commissioner explained this standard ensures due process for all parties involved in league disciplinary matters.

  "Number one, the burden is on the league if we're going to discipline a team, an owner, a player or any constituent members of the league," Silver said. "I think as with any process that requires a fundamental sense of fairness, the burden should be on the party that is, in essence, bringing those charges."

  The commissioner emphasized his commitment to treating all parties fairly throughout the investigation process. Silver referenced public perception and the potential for false conclusions in high-profile situations.

  "I'd want anybody else in the situation Mr. Ballmer is in now, or Kawhi Leonard for that matter, to be treated the same way I would want to be treated if people were making allegations against me," Silver said.

  Circumstantial Evidence Standards Detailed
  Silver clarified the league's approach to evaluating evidence beyond direct proof. The commissioner used a smoking gun analogy to explain how circumstantial evidence factors into investigations.

  "Then in terms of your specific question about circumstantial evidence, I was only quasi-joking with someone earlier that when people talk about a smoking gun, that's obviously circumstantial. It means the gun is still smoking; it must have recently fired," Silver explained.

  The NBA examines the totality of evidence when making determinations. Silver expressed reluctance to act based solely on appearances without substantial evidence supporting allegations.

  "I'd say in the case of the league, we and our investigators look at the totality of the evidence," Silver said. "I think whether mere appearance, just by the way those words read, I think as a matter of fundamental fairness, I would be reluctant to act if there was sort of a mere appearance of impropriety."

  Silver emphasized the goal of thorough investigation over rushed judgment. The commissioner noted public conclusions in high-profile cases often prove incorrect.

  "I think that the goal of a full investigation is to find out if there really was impropriety. Also in a public-facing sport, the public at times reaches conclusions that later turn out to be completely false," Silver said.

  Silver revealed he was unaware of the allegations until a recent Pablo Torre Finds Out podcast surfaced the information. The commissioner said he had never heard of Aspiration or any endorsement arrangement between Leonard and the company.

  "Well, when the podcast came out, it was news to me," Silver said. "I'd frankly never heard of the company Aspiration before, and I'd never heard a whiff of anything around an endorsement deal with Kawhi or anything around engagement with the Los Angeles Clippers."

  The NBA quickly determined the matter required investigation by an outside party. Wachtell Lipton, a New York law firm previously used by the league for similar investigations, is overseeing the probe.

  "We spoke internally. Rick Buchanan, our general counsel who oversees any investigations," Silver explained. "Rick had a conversation with Steve Ballmer, and we quickly concluded this was something that rose to the level that necessitates an investigation, and in fact one that's done outside of our office."

  When asked about potential penalties, Silver confirmed his authority extends across multiple areas. The commissioner can impose financial penalties, remove draft picks, and issue suspensions among other disciplinary measures.

  "My powers are very broad," Silver stated. "Full range of financial penalties - draft picks, suspensions, et cetera. I have very broad powers in these situations."

  Silver acknowledged the NBA operates differently than a court of law while maintaining the burden of proof standard. The league maintains broad authority to review all information and weigh evidence accordingly in disciplinary proceedings.

  "The answer is we're not a court of law at the end of the day, either, that we have broad authority to look at all information and to weigh it accordingly," Silver concluded.

  The commissioner emphasized his belief in due process throughout the investigation. Silver stressed the importance of allowing the external investigation to run its course before reaching conclusions.

  "Again, I would also say I've been around the league long enough in different permutations of allegations and accusations that I'm a big believer in due process and fairness, and we need to now let the investigation run its course," Silver said.

• Kawhi Leonard's Camp Asked Raptors For No-Show Endorsement Deal, Equity

  During Kawhi Leonard's 2019 free agency, his uncle Dennis Robertson made demands to the Toronto Raptors that line up almost perfectly with the terms of the star player's endorsement deal with Aspiration, sources tell Bruce Arthur of The Toronto Star. Robertson reportedly requested that the Raptors trade for Paul George plus give them an ownership stake in the Toronto Maple Leafs.

  Robertson also asked the Raptors for ownership stakes in outside companies associated with MLSE. The Raptors were also told they needed to match at least $10 million per year in additional sonship income. NBA teams are allowed to introduce players to team sponsors, but collective bargaining agreement rules prohibit them to negotiate those deals.

  It was also communicated that Leonard didn't "want to do anything" as part of the endorsement deal.

  MLSE realized that Leonard's camp wasn't asking for traditional sponsorship introductions, but no-show jobs instead. MLSE rejected those proposals.

  Leonard's $7 million per year deal with Aspiration began in April 2022, which was a few months after he signed a contract extension with the Clippers. Both Steve Ballmer and the Clippers have denied any involvement in the deal beyond the initial introduction.

• Aspiration Bid More Than Double Intuit For Clippers' Arena Naming Rights

  The Los Angeles Clippers received a bid from Aspiration for naming rights to their new arena worth nearly double that Intuit eventually paid, which was $550 million over 23 years. The Clippers decided to move forward with the offer from Intuit as they were the most established company.

  Aspiration instead executed a jersey patch sponsorship with the Clippers and other promotional activations.

  Aspiration has come into attention this year as they have gone bankrupt with one of its co-founders pleading guilty to framing investors. Aspiration also had a $28 million endorsement deal with Kawhi Leonard that the NBA is currently investigating amid allegations of potential salary cap circumvention on the part of the Clippers.

  Both the Clippers and Steve Ballmer have denied any violations of the NBA's collective bargaining agreement.

• NBA Hires Law Firm To Investigate Kawhi Leonard Endorsement Deal

  The NBA hired New York-based law firm Wachtell, Lipton, Rosen & Katz to investigate allegations that Kawhi Leonard's endorsement deal with a tree-planting company called Aspiration was made to circumvent the Los Angeles Clippers salary cap, sources told The Athletic.

  Pablo Torre originally reported that Leonard signed a four-year, $28 million deal with Aspiration that contractually required no services. Leonard also had a separate deal to receive $20 million in company stock.

  Steve Ballmer said he introduced Aspiration to Leonard, though had no knowledge of any endorsement deal. Ballmer then added that he was "conned" by the company.

  In addition to the law firm, the NBA will also have its own investigators to consult on the investigation.

  Wachtell Lipton is the same law firm that NBA used to investigate misconduct from Donald Sterling and Robert Sarver. Ownership of both the Clippers and Suns would change hands, with owners voting to remove Sterling and Sarver selling the Suns after getting suspended for one year.

  Ballmer is the richest owner in the league with a personal worth of $153 billion.