Kawhi Leonard completes a complicated return to the Toronto Raptors
Kawhi Leonard returned to the Toronto Raptors in mid-September in a trade that was followed by a two-year, $115m extension, a reunion reported on 19 October 2026. The move reunited Leonard with the franchise he led to an NBA title in 2019 and prompted renewed debate over his career and legacy.
When Leonard first arrived in Toronto in 2018 he presented himself as guarded, saying: “There’s just more questions you have to ask me in order for me to tell you about myself.” He had fallen out with the San Antonio Spurs amid a dispute over an injury that limited him to nine games in the 2017-18 season, and the Raptors acquired him in a swap that sent DeMar DeRozan elsewhere. Leonard produced a historic postseason, averaging 30.5 points, 9.1 rebounds, 3.9 assists and 1.7 steals en route to the franchise’s maiden championship and won his second finals MVP, adding to the award he claimed with the Spurs in 2014. At the 2018 press conference the team’s president, Masai Ujiri, said: “The narrative of not wanting to come to this city is gone,” addressing a fanbase that had seen American stars such as Vince Carter, Tracy McGrady, and Chris Bosh leave since the franchise opened in 1995.
Leonard left Toronto in 2019 after a protracted free agency overseen by his uncle, Dennis Robertson, opting to sign with the Los Angeles Clippers rather than remain with the reigning champions. Bruce Arthur said: “There wasn’t as much anger in 2019 as there was with Vince Carter or some of the other guys who left,” and reporting later revealed the Clippers arranged endorsement deals worth over $50m that violated NBA rules. Robertson was suspended for five years and Clippers owner Steve Ballmer received punishments including the loss of five first-round draft picks and a year-long suspension, while Leonard was fined $700,000 and the article notes he has earned $375m in salary so far in his career.
Arthur also reported Leonard was present when Robertson sought an ownership stake in the Toronto Maple Leafs and at least $10m per year in no-show sponsorships in 2019, a sequence Arthur summed up as: “So, perfect heist-type stuff from Kawhi.” The piece says Leonard has left fractured relationships at each franchise he has played for, with Spurs supporters still upset over the 2017-18 injury handling and Clippers fans “distraught about being left holding the bag without even a genuine apology from Leonard.”
Reactions among Raptors observers are conflicted. William Lou said: “There was a sense of defiance, especially the first year after Kawhi left [when the Raptors lost to the Boston Celtics in Game 7 of the Eastern Conference semi-finals] ... and there was a great deal of pride that went into that.” Arthur added: “I think the bottom line isn’t necessarily about a lack of moral reckoning by Raptors fans as much as: this guy’s so good that you forgive him, right?” The article recalls the public celebration following the 2019 title—“Two and a half million people on the streets of Toronto for the parade.”
The Raptors’ front office decided to pursue Leonard despite lingering frustration over his previous departure, the report says, noting the team had not won a playoff series since 2020 and endured three seasons of 30 wins or fewer. Last season the franchise improved significantly thanks to Scottie Barnes and a string of trades and draft picks, but the article describes the roster as a “relatively expensive, middle-of-the-pack team” until Leonard became available and pushed for a return. Leonard’s comment in the team-owned documentary Open Gym after the trade was: “This city took a liking to my family, and I took a liking to this city,” and he added: “Hopefully they embrace me back and [I] give them my all again, and we can make something special happen once again.” The Raptors acquired Leonard in mid-September in a deal that sent Brandon Ingram, Gradey Dick, two first-round picks, two second-round picks and a pick-swap to his former club.
The report notes extenuating circumstances surrounding the move—Leonard and the Clippers are under investigation by the Justice Department—and that Leonard chose Toronto over other offers from Miami, Minnesota, and Detroit. Lou said: “He deserves to have his jersey retired somewhere,” and added: “But due to the circumstances of his career, he kind of was a player without a home.” The article states that leading the Raptors back toward contention would “ensure him a jersey retirement ceremony, a first-ballot Hall of Fame induction, and Canadian sports immortality.” Diehard Raptors fan Imman Adan said: “It’s a little surreal having this guy who leaves after a championship, and you think the story’s done there, and then he becomes the biggest scandal in the NBA, and then somehow forces his way to the Raptors,” and added: “But I definitely think him coming back cements Toronto’s legacy.”
No matter how Leonard’s second tenure in Toronto plays out, his return is a stamp of approval — one that many Raptors fans have been waiting for since the franchise began.