Kawhi Leonard’s seven-year run with the Los Angeles Clippers has reached a controversial conclusion. Leonard joined the Clippers in 2019 after leading the Toronto Raptors to their first NBA championship and winning Finals MVP. His arrival also changed the franchise’s direction as Los Angeles moved aggressively to build a championship contender around him.
Leonard produced strong individual numbers during his Clippers tenure, averaging 25.1 points, 6.4 rebounds, 4.1 assists, and 1.7 steals. He also averaged a career-high 27.9 points while playing 65 games in the 2025-26 season.
The Clippers, however, never reached the NBA Finals with Leonard. Their run also ended with a major league investigation into salary-cap circumvention involving Leonard and the organization. The NBA fined the Clippers $30 million and stripped them of five first-round picks, while Leonard was fined $700,000.
Rich Eisen Delivers Brutal Verdict on Kawhi Leonard’s Clippers Acquisition
On The Rich Eisen Show, Rich Eisen delivered a harsh assessment of Leonard’s acquisition by the Clippers.
“Kawhi Leonard, his acquisition by the Los Angeles Clippers is now on the Mount Rushmore of the worst acquisitions in the history of professional sports on planet Earth. I don’t even know what could compare to this,” Eisen said.
Chris Brockman responded, “I mean, it knocks Herschel Walker off the top.”
Eisen then pointed to the chain of decisions that followed Leonard’s arrival in Los Angeles.
Leonard wanted Paul George alongside him, and the Clippers completed the blockbuster trade with the Oklahoma City Thunder. The deal sent Shai Gilgeous-Alexander and significant draft capital to Oklahoma City.
The Thunder eventually used that capital and players to build a contender, while the Clippers failed to reach the Finals.
Los Angeles reached the Western Conference Finals in 2021, but Leonard was sidelined after suffering an ACL injury during that playoff run.
The Clippers also struggled to keep their stars healthy. Leonard played at least 65 games only twice during his Clippers tenure and missed the entire 2021-22 season.
Eisen also referenced the NBA investigation into the Clippers’ dealings with Leonard. The league found multiple salary-cap violations and imposed significant penalties on the organization.
The Clippers must forfeit first-round picks in 2029, 2030, 2031, 2032 and 2033. Owner Steve Ballmer was suspended for one year, Gillian Zucker for one year, and Lawrence Frank for six months.
The Clippers rejected the NBA’s findings and said they would challenge the penalties through arbitration.
From the cost of Leonard’s Clippers tenure to what comes next, the NBA ruling has also cleared the path for his next chapter.
Kawhi Leonard Expected to Return to Toronto With Extension Looming
“The expectation is there will be an extension here to come with Kawhi Leonard”
While the NBA announced significant penalties for the Los Angeles Clippers and Kawhi Leonard on Wednesday, the Clippers and Toronto Raptors are still moving forward with plans for Leonard’s trade to Toronto.
“As of right now, both sides—the Clippers and Raptors—are moving forward as if the trade is going to happen,” ESPN’s Shams Charania said Thursday on The Pat McAfee Show. “Both sides have already spoken Wednesday night and have the intention of moving forward here with this trade.”
Charania also said, “The expectation is there will be an extension here to come with Kawhi Leonard.”
Leonard also addressed his return to Toronto following the NBA’s announcement, writing, “As I return to Toronto, I am focused on what I can control, closing this chapter, and moving forward with a clean slate.”
The 35-year-old Leonard would return to the Raptors after previously spending the 2018-19 season with the franchise. He led Toronto to its first NBA championship that season and won Finals MVP before leaving for the Clippers.
The trade to Toronto was initially paused while the NBA investigated the Clippers’ dealings with Leonard. The original framework sent Leonard to the Raptors for Brandon Ingram, Gradey Dick, multiple draft picks and additional draft considerations.
Leonard’s current contract is set to enter its final season in 2026-27, making an extension an important part of Toronto’s plans if the trade is completed.
The move would also give the Clippers draft capital following the NBA’s decision to strip the organization of five first-round picks as part of its penalties for salary-cap circumvention. Leonard was fined $700,000, while the Clippers were fined $30 million.
Clippers governor Steve Ballmer was also suspended for one year from all league and team activities.
The Clippers have rejected the NBA’s findings and said they plan to challenge the penalties through arbitration.
Kawhi Leonard Signing Ripped as One of the Worst Moves in Sports History