The Toronto Raptors may see a massive hurdle in their acquisition of Kawhi Leonard from the LA Clippers.
According to ESPN’s NBA insider Brian Windhorst, the Raptors may not acquire Leonard via trade with the Clippers if the league denies the trade due to Leonard being a detriment to Toronto due to the ongoing league investigation about an alleged salary circumvention between him and the Clippers.
The issue stems from the Clippers’ use of a third-party green banking startup called Aspiration to funnel under-the-table money to Leonard, circumventing the NBA’s salary cap rules.
“Adam Silver, 26 days ago, announced that it was time for the investigation to end. We have no results of the investigation,” Windhorst said in ESPN’s Get Up. “However, the league would not approve a trade involving Kawhi Leonard if they thought they would be detrimental to the team acquiring him. That’s number one.”
NBA’s Aspiration Investigation Has Taken An Extended Period Of Time
GettyINGLEWOOD, CALIFORNIA – MARCH 25: Kawhi Leonard #2 of the Los Angeles Clippers controls the ball against the Toronto Raptors in the second half at Intuit Dome on March 25, 2026 in Inglewood, California. (Photo by Ronald Martinez/Getty Images)
As revealed by journalist Pablo Torre, Clippers owner Steve Ballmer made a substantial investment in Aspiration in 2021, while the Clippers signed a 23-year, $300 million sponsorship deal with the company.
In 2022, Aspiration signed star Kawhi Leonard to a separate $28 million endorsement contract, which is believed to be a “no-show” agreement to bypass the NBA salary cap.
Aspiration then filed for bankruptcy. Both Steve Ballmer and Leonard have repeatedly denied any wrongdoing.
While the NBA was doing its investigation, Leonard, who is 34 years old, had an impressive season, where he averaged 27.9 points, 6.4 rebounds, and 3.6 assists across 65 regular-season games to be named in the All-NBA Second Team.
The Clippers finished with a 42-40 record and were eliminated by the Golden State Warriors in the play-in tournament.
A trade to the Raptors would reunite him with the franchise he led to the 2019 NBA championship before signing with the Clippers, just a month after winning the title.
Adam Silver Talks About Kawhi Leonard, LA Clippers Investigation
GettyLAS VEGAS, NEVADA – DECEMBER 16: NBA Commissioner Adam Silver speaks during a news conference before the championship game of the Emirates NBA Cup between the San Antonio Spurs and the New York Knicks at T-Mobile Arena on December 16, 2025 in Las Vegas, Nevada. The Knicks defeated the Spurs 124-113. (Photo by Ethan Miller/Getty Images)
The NBA’s investigation of the Aspiration scandal has taken more than 10 months already, with no resolution so far.
Adam Silver talked about the league’s investigation during the NBA Finals last month.
“The most important thing is that we get it right. I certainly hear many things all the time about the perception of what really happened or didn’t happen here. I wouldn’t be doing my job if, ultimately, I issue (his) determination based on perception. My job is to follow the facts,” Silver said.
“The team has to understand what situation they are going to be operating under, and so do the 29 other teams… We can’t be investigating forever.”
Without a resolution in sight, the league could find themselves on the crossroads of a potential Leonard deal amid the NBA investigations.
Leonard is in the final guaranteed year of his contract with the Clippers, which will earn him $50.3 million for the 2026-27 season.
In the latest report from ESPN’s Shams Charania, Leonard is willing to sign a long-term contract extension with the Raptors if he is let go by the Clippers.
Toronto Raptors Hit With Bad News On Potential Kawhi Leonard Trade With LA Clippers