TodayTuesday, September 08, 2026

Kawhi Leonard Cleared the NBA’s Biggest Hurdle. The Raptors Are Now Expected to Extend Him.

Shams Charania reports both sides are moving forward after Wednesday's ruling, and that a Leonard extension in Toronto is now expected to come.
September 8, 2026
3 mins read
Kawhi Leonard during his time with the Los Angeles Clippers before his trade to the Toronto Raptors
Kawhi Leonard, whose contract survived the NBA's cap circumvention investigation, is now expected to sign an extension with the Toronto Raptors. [Image Source: Getty Images / Bleacher Report]

TORONTO — The Toronto Raptors spent the summer doing something unusual for a franchise that had just agreed to one of the blockbuster trades of the offseason: almost nothing. While other teams signed players, adjusted rosters, and prepared for training camp, Toronto waited for a league ruling that could either deliver them one of the NBA’s best two-way players or leave them with nothing but their own picks back and a summer of lost opportunity.

The ruling came Wednesday. And then on Thursday, ESPN’s Shams Charania appeared on The Pat McAfee Show and said what Toronto had been waiting months to hear. The Kawhi Leonard trade is moving forward. Both the Clippers and the Raptors have spoken. The expectation, Charania said, is that an extension will follow.

That confirmation changes what the 2026-27 Raptors look like. It changes what the rest of Kawhi Leonard’s career looks like. And it begins, finally, to close the longest chapter in one of the NBA’s most complicated player-franchise stories.

The ruling that cleared the path was far from gentle on the Clippers. The NBA stripped the franchise of five first-round draft picks, fined owner Steve Ballmer $30 million and suspended him for one year, and levied a $700,000 fine on Leonard for his role in the salary cap circumvention scheme. Los Angeles has said it “vehemently rejects” the findings and will challenge the penalties. What the Clippers could not challenge, and what the Raptors were watching most closely, was whether the league would void Kawhi’s contract entirely, as it did to Joe Smith’s agreement with the Minnesota Timberwolves in 2000. It did not.

The difference between the two cases mattered. Smith’s arrangement with Minnesota was a secret side deal, a verbal promise of future contract terms made outside official league channels. Leonard’s deal was his actual contract. CBS Sports reported that the NBA’s investigators found violations in how the Clippers structured income he received off the court, not in the contract itself, a distinction that was enough to fine him without voiding the agreement. Kawhi received a $700,000 fine and no suspension. His contract, which runs through the 2026-27 season, is intact. The league found no proof, Charania noted, that Leonard had knowledge of the circumvention scheme.

So is the trade.

Kawhi Leonard of the Los Angeles Clippers whose contract was upheld by the NBA's cap circumvention investigation
The NBA’s investigation cleared Kawhi Leonard of knowingly participating in the Clippers’ cap circumvention scheme, leaving his contract intact for the Toronto trade. [Image Source: Getty Images / CBS Sports]
Toronto agreed to acquire Leonard from Los Angeles in early July, sending Brandon Ingram, Gradey Dick, unprotected first-round picks in 2031 and 2033, and additional future assets in a deal that drew sharply divided grades when it was announced. When the NBA’s nine-month investigation into the Clippers paused the trade, Toronto stopped moving. The freeze reportedly cost the Raptors any chance to pursue a DeMar DeRozan reunion and limited their flexibility heading into the offseason. Every other personnel decision filtered through one question: does this deal close or not?

Thursday’s report from Charania says it does. More than that, it says the extension is expected. Leonard’s current deal expires after next season, making the extension window the central question about how seriously Toronto plans to build around him. He hired a new agent in July specifically to handle those negotiations. Bleacher Report confirmed that Charania’s language on The Pat McAfee Show was specific: “The expectation is there will be an extension here to come with Kawhi Leonard.” An extension, if finalized, would lock him in through at least 2028-29, pairing him with Scottie Barnes across what could be the most consequential years of the 24-year-old’s development.

“As I return to Toronto, I am focused on what I can control, closing this chapter, and moving forward with a clean slate,” Leonard said in a statement when the trade was first announced. The phrase landed with particular weight for a player whose exits from San Antonio and Los Angeles had both left unresolved questions behind them.

Leonard turns 35 next month. He has played more than 68 games in a season only twice in the past eight years. The 65 games he played last season, combined with career-best scoring numbers, gave the Raptors the clearest argument for his durability they could have asked for, at a moment when the investigation could have made the whole arrangement pointless. Whether that holds through another deep playoff run, through a contract worth at least two more seasons at his age and his medical history, is what any extension will be gambling on.

Scottie Barnes, the 24-year-old the Raptors have built their post-rebuild era around, is why the gamble makes sense even under those conditions. An extended Leonard gives Barnes a co-star with two championship rings and a lifetime of defensive instincts to develop alongside during what should be the prime contract years of his career. Without the extension, Toronto would face a 2027 offseason in which one of the more interesting young players in the league enters free agency and the team loses the player they paid two unprotected first-round picks to bring back.

The specific terms, the length, the value, the structure, were not part of Charania’s Thursday report. What he named was the expectation, not the numbers, and there is real distance between those two things when one party is coming off an NBA investigation and the other is a franchise that spent the summer in salary-cap suspension. Those details, when they arrive, will either justify the months Toronto endured or raise fresh questions about the cost of endurance.

For now, the Raptors have what they spent months hoping for: Kawhi Leonard headed to Toronto, his contract standing, and an extension expected to follow. The chapter closed. The next one has not started yet.

Jennifer Hicks

Jennifer Hicks

Jennifer Hicks is a columnist and political commentator writing on a large range of topics.

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