Kawhi Leonard turned 35 last month coming off the best scoring season of his career, and for a few days it looked like he would spend his 36th year back where he became a champion. Instead, the trade sending him from the Los Angeles Clippers to the Toronto Raptors is parked in limbo, and it will stay there until the NBA finishes digging into how the Clippers have paid him.
The Raptors made it official on Thursday, saying the deal cannot close while the league investigates the Clippers. The teams agreed on the framework on June 30, with Toronto sending Brandon Ingram, Gradey Dick, two first-round picks, two second-round picks and pick swaps to Los Angeles for Leonard, a move that would have reunited him with the franchise he carried to its only championship in 2019. Nine days later, that agreement is on ice.
The Raptors were direct about why. The league office told the team it would assume the risk of any outcome from the Clippers investigation if the trade went through with Leonard still under its cloud, so Toronto chose to wait. The Raptors said in a statement that they remain eager to bring Leonard back and want a swift resolution for their players, their organization and their fans.
What the NBA Is Investigating
The league opened its probe in September into a $28 million endorsement contract between Leonard and Aspiration Fund Adviser LLC, a sustainability-focused company that filed for bankruptcy in 2025, after journalist Pablo Torre reported on the arrangement. The case tightened last month when Aspiration co-founder Joseph Sanberg was sentenced to 14 years in federal prison for defrauding investors and lenders of more than $248 million, a conviction that has nothing to do with Leonard directly but sits at the center of the NBA’s questions about whether the Clippers used the company to funnel him money outside the salary cap.
The investigation is being carried out by outside counsel at Wachtell Lipton, and the league has not set a deadline. A spokesman said only that the firm is expected to finish its work in the coming weeks. Commissioner Adam Silver addressed the pace of the probe last month at the NBA Finals, saying his instruction to investigators is that they cannot investigate forever and need to wrap it up, while adding that getting the conclusion right matters more than getting it done fast.
The Clippers have pushed back hard on the premise. In a statement Thursday, the team said Sanberg and Aspiration are at the heart of the investigation and denied ever funneling money to Leonard through the company, framing the Clippers as victims of Sanberg’s fraud rather than participants in it. The team said it remains confident the league will ultimately confirm it did nothing wrong.
Why the Wait Could Cost the Clippers
The NBA has only handed down one true salary-cap-circumvention penalty of this scale, and it is the benchmark every front office measures a case like this against. When the league found in 2000 that the Minnesota Timberwolves had a secret side agreement with Joe Smith worth as much as $86 million over seven years, hidden behind a one-year, cap-friendly contract, commissioner David Stern stripped Minnesota of five first-round draft picks, fined the franchise $3.5 million and suspended both general manager Kevin McHale and owner Glen Taylor for a year. Two of those five picks were later returned, but the punishment remains the harshest cap penalty in league history, the shadow hanging over the Clippers while Wachtell Lipton works through Leonard’s Aspiration deal.
The Toronto History at Stake
The player at the center of it all is coming off a season that argues he still has plenty left. Leonard averaged a career-high 27.9 points for the Clippers in 65 games this past season, adding to a resume that already includes seven All-Star nods, seven All-NBA selections and Finals MVP honors with two different franchises. His lone season in Toronto in 2018-19 remains the standard: 26.6 points, 7.3 rebounds and 3.3 assists in 60 games, then 28.5 points, 9.8 rebounds and 4.2 assists through the playoffs on the way to the Raptors’ only title, the run that made him a folk hero in a city he is now trying to get back to.
For now, none of that history moves the deal forward. The trade Toronto and Los Angeles shook hands on stays frozen until the league’s outside investigators decide whether the Clippers broke the rules to keep him, and both franchises are left waiting on a timeline nobody controls. For more on how this offseason has unfolded across the league, browse Playbook Wire’s full basketball coverage as the situation develops.
