In an NBA offseason dominated by LeBron James and unrelated Lakers drama, Kawhi Leonard received a surprising amount of attention. With Leonard, the Los Angeles Clippers and team owner Steve Ballmer still the subject of a league investigation, a sudden June trade of Leonard to the Toronto Raptors brought that situation back to the forefront.
Was the NBA’s investigation still active? And would the league step in, with Leonard now on his way to a different team?
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Those questions were both answered with a resounding “yes.” The trade was officially put on hold after both teams confirmed the NBA was still looking into the situation.
Given that it’s been nearly a year since the NBA launched its current investigation, it’s worth remembering why Ballmer, Leonard and the Clippers are under investigation in the first place.
Below is a full timeline of the events leading up to the NBA’s investigation and every significant development since the league announced it would look into Leonard’s original agreement with the Clippers.
July 6, 2019: Kawhi Leonard signs with the Clippers
Fresh off a championship run with the Raptors, Leonard — a free agent — decided to leave Toronto to sign with the Clippers. He originally joined the team on a three-year, $103 million deal. That same offseason, the Clippers traded for Paul George. That influx of talent was supposed to make the Clippers a premier contender in the Western Conference.
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Dec. 23, 2019: Reports suggest NBA investigated Clippers over Leonard signing
A few months after Leonard signed, a report from The Athletic detailed the superstar’s free agency, which resulted in an NBA investigation. According to that report, one member of Leonard’s camp — Dennis Robertson — reportedly asked teams for impermissible benefits if they wanted to sign Leonard. Robertson is also known as “Uncle Dennis,” and is Leonard’s actual uncle.
This was the key portion of The Athletic’s report:
Sources say the league was told that Robertson asked team officials for part ownership of the team, a private plane that would be available at all times, a house and — last but certainly not least — a guaranteed amount of off-court endorsement money that they could expect if Leonard played for their team. All of those items, to be clear, would fall well outside the confines of the league’s collective bargaining agreement.
It was believed Robertson made those requests to both the Raptors and the Los Angeles Lakers.
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The NBA looked into whether the Clippers granted any of those requests, but an investigation found no evidence that was the case.
Months earlier, the NBA revamped its tampering and free-agent rules, perhaps as a response to the rumors surrounding Leonard’s free agency.
Sept. 3, 2025: Pablo Torre prompts NBA to open another investigation into Clippers
Between December 2019 and August 2025, things are mostly quiet on the Leonard front. While he remained an elite player on the court, Leonard missed time here and there with injuries with the Clippers. Despite his original contract running out, Leonard continued to re-sign with the club, eventually landing on a deal that kept him under contract through the 2026-27 NBA season.
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The Leonard-George pairing didn’t work out as well as intended, with the Clippers failing to win a title with the two stars. George eventually left for the Philadelphia 76ers, and Leonard was set to open the 2025-26 NBA season with hopes of keeping the Clippers in contention in a tough Western Conference.
But a little over a month before the 2025-26 NBA season, journalist Pablo Torre released an episode of his podcast “Pablo Torre Finds Out” that accused the Clippers of using a sponsor to pay Leonard for “no-show jobs” as a way to circumvent the NBA salary cap.
That company — named Aspiration — was funded by Ballmer. During the show, Torre argued that Aspiration paid Leonard $28 million to essentially do nothing. Leonard would only be paid if he remained a member of the Clippers, per Torre. If Ballmer was aware of that arrangement, or encouraged it, that could constitute the Clippers circumventing the NBA salary cap, a significant violation. One former employee of Aspiration, which has since gone bankrupt, said they were told the agreement with Leonard was a way for the team to “circumvent the salary cap.”
That same day, the Clippers released a statement denying all accusations made by Torre. The team said it was not unusual for team sponsors to reach agreements with players and that Ballmer and the team had no oversight of Leonard’s agreement with Aspiration.
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Given all the evidence revealed in Torre’s program, the NBA announced it would launch an investigation into the situation.
Sept. 5, 2025: Steve Ballmer says he was conned by Aspiration
In his first interview since Torre’s podcast, Ballmer claimed he was the victim of fraud by Aspiration co-founder Joseph Sanberg.
“These are guys who committed fraud. Look, they conned me. I made an investment in these guys thinking it was on the up and up. And they conned me. At this stage, I have no ability to predict why they might have done anything they did.”
Ballmer also reiterated that the Clippers introduced Leonard to Aspiration, which is not against NBA rules. From that point, Ballmer said the team was not involved in Leonard’s negotiations with the company.
Sept. 10, 2025: Adam Silver addresses NBA investigation into Clippers, Leonard
Following a Board of Governors meeting in September, NBA commissioner Adam Silver publicly addressed the Leonard investigation for the first time. He didn’t get into specifics, merely saying the NBA would need clear evidence suggesting the Clippers tried to circumvent the NBA salary cap.
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Silver said the “mere appearance of impropriety” would not be enough to force the league to act.
Sept. 11, 2025: Torre unearths more evidence suggesting Clippers funded payments to Leonard
Torre, meanwhile, kept releasing episodes providing more suspicious evidence suggesting the Clippers may have known about and funded Leonard’s deal with Aspiration.
Torre’s next episode into the matter focused on Clippers co-owner Dennis Wong, who reportedly invested a hefty amount of money into the failing business just days before Leonard was set to be paid. It provided more evidence suggesting the Clippers were aware of the agreement between Leonard and Aspiration.
Steve Ballmer has owned the Clippers since 2014.
(Allen Berezovsky via Getty Images)
Sept. 16, 2025: Ballmer says he’s confident he’ll be cleared in NBA investigation
During an appearance at Sports Business Journal’s Drive event, Ballmer said he welcomed the NBA investigation and remained steadfast that the team did not violate any rules when signing Leonard.
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Sept. 18, 2025: Ballmer reportedly sent payments to Aspiration around time Leonard was due to be paid
Torre put out yet another episode of his program, this one focusing on payments Ballmer made to Aspiration just before Leonard was set to be paid. Torre found multiple instances in which the team or a member of the team made significant payments to Aspiration just days before Aspiration sent a large payment to Leonard.
There was still no smoking gun directly confirming Ballmer paid Leonard extra money through Aspiration, but enough evidence had been uncovered by Torre that the NBA couldn’t look away.
Sept. 19, 2025-May 3, 2026: NBA goes silent, Torre keeps posting
After acknowledging a new investigation was launched, the NBA mostly went silent on all things involving the Clippers and Leonard. Torre, meanwhile, continued to post episodes with more evidence casting suspicion on the team and its actions. Torre posted one more video in September, and then a seven-and-a-half-hour compilation of every single episode on the topic in December.
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In January, Torre started posting new videos on the Leonard situation. He posted a new video roughly every month between January and June, providing more evidence and going in depth on questionable agreements involving Leonard, Ballmer, the Clippers and the team’s sponsors.
May 4, 2026: Torre wins Pulitzer Prize for unearthing Leonard situation
Torre received one of journalism’s highest honors in May, when it was announced his show won a Pulitzer Prize for audio reporting. Torre won the award thanks to the program’s deep dive into the Leonard situation.
June 1, 2026: Aspiration co-founder sentenced to 14 months in prison
Aspiration co-founder Joseph Sanberg was sentenced to 14 months in federal prison after pleading guilty to two charges of wire fraud.
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Two months earlier, Ballmer had his attorneys send a letter to the judge presiding over Sanberg’s case. That letter outlined all the ways in which Ballmer believed he was defrauded by Sanberg and Aspiration.
June 30, 2026: Clippers trade Leonard to the Raptors
With the investigation still ongoing, the Clippers decided to trade Leonard to the Raptors. From a basketball perspective, the move made sense. The Clippers failed to make the playoffs despite Leonard posting excellent numbers last season. With the 35-year-old entering the final year of his contract, the Clippers had legitimate reasons for trading away the aging star.
The optics, however, were questionable at best. And given the investigation was still underway, it was unclear whether the NBA would be forced to address the issue now that Leonard was involved in a significant offseason transaction.
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July 9, 2026: Clippers, Raptors say Leonard deal on hold for now
The NBA did address the trade, though not publicly. Both the Clippers and Raptors confirmed the Leonard deal was on hold until the NBA completed its investigation into the matter.
The Clippers used the opportunity to again reiterate that they did not funnel money to Leonard through Aspiration. The team added that it expects the trade to eventually be completed.
“On June 30, we reached an agreement in principle to trade Kawhi Leonard to the Toronto Raptors,” the team said. “We have since been informed that the trade can only be finalized if the Raptors’ ownership group assumes the risk of penalties related to Kawhi’s contract that could theoretically result from the ongoing investigation. The investigation is ongoing, and we expect the trade to be finalized following its conclusion.”
The Raptors said they were told they “would assume the risk of any potential outcome of the investigation impacting Kawhi” if they allowed the trade to go through now. With that uncertainty lingering, the team said it would wait until the league’s investigation was complete before moving forward with the deal.
NBA Commissioner Adam Silver addressed the Kawhi Leonard investigation in July.
(Anadolu via Getty Images)
July 15, 2026: Silver publicly addresses Leonard trade, investigation
At the Summer League, Silver addressed both the Leonard trade and the status of the league’s investigation. Silver said the league did not pause the Leonard deal, instead saying both the Clippers and Raptors made that decision.
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Regarding the actual investigation, Silver said he hoped to have things resolved over the summer, before the start of the 2026-27 NBA regular season.
That same day, it was reported that the NBA was looking into a separate endorsement deal Leonard had with a different company.
July 29, 2026: Reports emerge suggesting Leonard investigation could continue into 2027
While Silver said he hoped the NBA’s investigation would cease before the start of the 2026-27 NBA season, reports emerged suggesting it could extend into 2027.
An ESPN report claimed the issue could get pushed to next year, depending on whether all parties agreed with the findings of law firm Wachtell Lipton, which the NBA hired to perform its investigation. That report seemed to suggest the league’s investigation was over … or at least close to being concluded.
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Aug. 7, 2026: Torre reports on another questionable Leonard deal
Torre dropped another bombshell in August, reporting on a deal Leonard signed with the company Daktronics. Despite seemingly not doing any endorsement work for the company, Leonard reportedly received millions from Daktronics.
Torre claimed that some people who worked on the Intuit Dome were “openly” joking about the deal as being “1,000% a way to circumvent the salary cap.”
Aug. 17, 2026: ESPN reports NBA has no evidence Ballmer funneled money to Leonard
The NBA’s investigation into Leonard, the Clippers and Ballmer reportedly found no evidence Ballmer funneled money to Leonard, ESPN reported.
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Despite that, the NBA was still looking into other potential violations by the team, with ESPN reporting “both sides have been negotiating a resolution to the investigation.”
Shortly after that report emerged, the NBA said there were inaccuracies in ESPN’s reporting. ESPN stood by its article.
In response to that piece, the Clippers once again released a statement claiming they did not funnel money to Leonard. The team also reiterated that introducing players to sponsors is not against NBA rules.
ESPN also reported that any punishment from the league would likely be taken to arbitration by Ballmer and/or the NBPA, which wouldn’t look kindly on a player being punished for working with a team sponsor.
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Oct. 20, 2026: Opening night of the 2026-27 NBA season
The 2026-27 NBA regular season is set to begin Oct. 20. Three games will occur that day, none of which will feature either the Clippers or Raptors. Those teams will play their first games the following day, Oct. 21.
It’s unclear whether Leonard will be eligible to play in that contest … or which team he’ll be on when the regular season begins.
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