Los Angeles Clippers owner Steve Ballmer has repeatedly insisted his organization did nothing wrong regarding the Kawhi Leonard-Aspiration scandal. He has publicly stated, “I feel quite confident that we abided by the rules,” and told the Sports Business Journal’s Drive event that “this too shall pass” while welcoming the NBA inquiry. His defense hinges on being a victim of fraud, claiming he was “conned” by Aspiration’s founders. The NBA reopened the investigation after reporting showed Aspiration paid Kawhi Leonard a controversial four-year, $28 million endorsement deal, and Aspiration co-founder Joe Sanberg later pleaded guilty to defrauding investors.
This stance of innocent victimhood is now facing its most serious challenge. Until now, the obstacles in that defense had come in the form of controversial paperwork from Pablo Torre that hinted at a very concerning chronology of events that suggest Ballmer and the Clippers knew exactly what they were doing. Now, a new investigative report has surfaced, containing what many are calling a “smoking gun” that directly contradicts Ballmer’s narrative of being a duped investor.
That update once again came from Pablo Torre and his recent episode. It dug through court filings and interviews on being insisted by Mark Cuban. And then aired a series of jaw dropping revelations. As Torre put in the report “We should point out here that there’s another glaring revelation in these documents … 90% 90% of Interprivate shareholders effectively bailed on the premise of aspiration. They redeemed their shares at roughly $10 10 cents per share, tanking the company”. An anonymous Aspiration employee told Torre “Ballmer invested $10 million more at a $23 share price. Over 23, just over $23. So more than double what he invested in as a share price in 2021”. As sports commentator Dan Le Batard said on the podcast “This is lunacy. It really it really is”.
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The latest report effectively lays out that if in truth Ballmer was an “unsuspecting investor” in the company, the investment was itself a peculiar financial decision. Why will the Clippers owner, whose net worth is over $150 billion, make such an investment in a tanking comany at such exorbitant rates? The former Microsoft CEO purchased the Clippers for $2 billion back in 2014 and the franchise is now worth $5.5 billion. His portfolio is littered with such investments that obviously contributed to his net worth.
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The timing that Torre laid out is striking and specific. And mapping it into a clear timeline raises even more questions. Steve Ballmer first invested $50 million in Aspiration on September 14, 2021, and the Clippers announced Aspiration as a major sponsor later that month. On April 1, 2022 the Clippers wired $3 million for carbon credits and on April 4, 2022 they wired another $32 million, the same day Leonard signed his Aspiration deal.
On June 17, 2022 another $21 million went to Aspiration. Leonard got a $1.75 million payment on July 6, 2022. In December 2022 Clippers minority owner Dennis Wong invested $1.99 million on December 6 and Leonard then received $1.75 million on December 15. Then on March 9, 2023 Steve Ballmer pumped in almost $10 million even though Aspiration’s troubles were already public. Those links make the transactions look less like coincidence and more like rescue moves.
Commissioner Adam Silver has said the league will only act with evidence and not on appearances. Telling reporters “I would be reluctant to act if there was a mere appearance of impropriety. I think the goal of a full investigation is to find out if there really was impropriety”. Still the NBA has broad powers under the collective bargaining rules to fine teams, seize draft picks, void contracts and require repayment if it finds unauthorized agreements or circumvention.
The league hired the law firm Wachtell Lipton to probe the matter, the same firm that has handled prior major investigations, and the Minnesota Timberwolves precedent from 2000 shows the penalties can be severe when the league finds secret payments. With mounting documentation and a whistleblower testimony, the pressure on Silver to deliver a meaningful ruling is only increasing.
If the new reporting holds up, the consequences for Kawhi Leonard could be dramatic even though he is the player at the center of a business deal that was run outside team payroll. ESPN and others have already reported the Clippers are shifting away from building around Leonard, and a former team staffer put it bluntly “They’re done building around [Kawhi],” he said. Adding “They know that and he knows that”. That organizational pivot makes any league punishment easier to impose without upending a franchise strategy.
The emerging picture of Steve Ballmer doubling down with a nearly $10 million investment when Aspiration’s troubles were public makes a defense of ignorance much harder to sustain. The next phase is legal and procedural, and it will determine whether Kawhi Leonard pays a personal price for an owner’s risky decisions.
Setting the Example: Why Leonard Must Pay the Price
Commissioner Adam Silver faces a defining moment for the league’s integrity. His public declaration that salary cap circumvention is a “cardinal sin” means the punishment must be severe enough to deter any owner from ever attempting a similar scheme. Historical precedent, namely the 2000 Minnesota Timberwolves case where Joe Smith was punished for a secret deal, demands that the player involved also faces consequences. The rules are designed to maintain competitive balance, and allowing Leonard to escape penalty would signal that players can profit from such arrangements.
The NBA’s Collective Bargaining Agreement provides Silver with a full range of options. For a violation of this scale, the maximum penalties include voiding Leonard’s current contract with the Clippers, fining him up to $350,000, and even requiring him to return the money received from Aspiration. Voiding the contract would be the nuclear option, preventing him from re-signing with the Clippers and creating a massive, unprecedented shakeup in the league’s power structure. This is the level of deterrent needed.
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The argument for including Leonard in the punishment is strengthened by the sheer scale of the alleged scheme. The $28 million deal dwarfed Aspiration’s agreements with other celebrities and involved clauses that allowed Leonard to refuse any work “not consistent with his beliefs,” which he apparently did. He never publicly promoted the company. Failing to punish the player who received such a clear, massive advantage outside the salary cap would render the entire system meaningless and invite chaos.
Ultimately, Silver’s legacy as a commissioner who upholds fairness is on the line. The other 29 team owners are watching closely. If a player of Kawhi Leonard’s stature is not held accountable for his role in this, it would embolden every other team and star to seek their own creative loopholes, destroying the competitive parity the cap is designed to protect. For the health of the league, the punishment must be comprehensive, impacting both the reckless owner and the superstar who benefited.