When Kawhi Leonard became a Toronto Raptor for the first time in the summer of 2018, he looked shellshocked. “There’s just more questions you have to ask me in order for me to tell you about myself,” he said, introducing himself to an organization and city he reportedly had no interest in joining.

Leonard had fallen out with his former team, the San Antonio Spurs – one of the most respected franchises in professional sports – due to differences in opinion about an injury that had limited him to just nine games in the 2017-18 season. The Los Angeles native had hoped to end up in southern California, but instead the Raptors risked it all by swapping franchise cornerstone DeMar DeRozan for one year of an injured, malcontent Leonard. It worked: Leonard led the Raptors to their maiden championship on the back of a historic playoff run, averaging 30.5 points, 9.1 rebounds, 3.9 assists and 1.7 steals en route. Leonard won his second finals MVP to go alongside the one he had claimed with the Spurs when he helped them to the title in 2014.

“The narrative of not wanting to come to this city is gone,” the team’s president, Masai Ujiri, said at that 2018 press conference, speaking to insecure Raptors fans who had watched American players like Vince Carter, Tracy McGrady, and Chris Bosh leave Toronto since the franchise opened its doors in 1995. “We should move past that. Believe in this city. Believe in yourselves … We are proud of who we are.”

But even a historic season wasn’t enough to convince Leonard to stay north of the border. After a long and contentious free-agency period managed by his uncle, Dennis Robertson, Leonard spurned the reigning champions in favor of his hometown Los Angeles Clippers. “There wasn’t as much anger in 2019 as there was with Vince Carter or some of the other guys who left,” says Bruce Arthur, who has covered Leonard since 2018 for the Toronto Star. “I think he was given a little bit of special dispensation because he was going home, because he had delivered a title, and because I never felt like there was ever a connection outside of Kawhi the basketball player, with Toronto.”

Raptors fans’ anger was instead directed towards the Clippers, who not only showed up to almost every Raptors game during the championship season, but who also, we now know, went under the table to ensure Leonard signed lucrative endorsement deals totaling over $50m – violating the NBA’s salary cap rules.

Robertson was suspended for five years and Clippers owner Steve Ballmer was handed the harshest punishment in NBA history, including the loss of five first-round draft picks and a year-long suspension. However, thanks to a side-deal between the NBA and its Players Association executed to avoid arbitration, Leonard was given a relatively light $700,000 fine (he has earned $375m in salary so far in his career).

“Kawhi’s … gotten away really clean from what is obviously out-of-bounds behavior,” says Arthur, who reported that Leonard – as much as he pleads ignorance to all this – was in the room when Robertson asked the Raptors for an ownership stake in the Toronto Maple Leafs and at least $10m per year in no-show sponsorship deals in 2019. “So, perfect heist-type stuff from Kawhi.”

Despite being one of the greatest players of his generation, the 35-year-old has burned bridges on his way out of every franchise he’s played for. Spurs fans are still upset by the way his injury was handled in 2017-18, while Clippers fans are distraught about being left holding the bag without even a genuine apology from Leonard. But Raptors fans have much more complicated feelings towards the seven-time All-Star – arguably the best player in franchise history.

On the one hand, “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,” says William Lou, the host and creator of the Hello and Welcome podcast. But as time went on, “The Clippers were humbled in a basketball sense. They never could get that version of Kawhi … that Toronto got in their one year, and so it’s hard to be too mad.”

Arthur says Raptors fans will always associate Leonard with the championship win. “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?” says Arthur. “The [championship] was the greatest moment in franchise history by galaxies. Two and a half million people on the streets of Toronto for the parade. That was one of the best days Toronto’s ever had.”

The sentiment was seemingly shared by the organization. Despite being frustrated by the way his previous free agency unfolded, the Raptors front office couldn’t pass up the opportunity to grab the lifeline Leonard represented – even in his mid 30s. The Raptors have failed to win a playoff series since 2020, a stretch that includes three grim seasons of 30 wins or fewer. Last season, the franchise pulled itself out of the dregs of the league thanks to a star leap from 25-year-old Scottie Barnes and a handful of smart trades and draft picks, but the Raptors looked like a relatively expensive, middle-of-the-pack team with a difficult path towards contention until Leonard not only became available, but pushed his way towards Toronto.

“This city took a liking to my family, and I took a liking to this city,” Leonard said in the team-owned documentary series Open Gym after the Raptors traded Brandon Ingram, Gradey Dick, two first-round picks, two second-round picks and a pick-swap for him in mid-September. “Hopefully they embrace me back and [I] give them my all again, and we can make something special happen once again.”

Although there were extenuating circumstances leading to Leonard’s return – he and the Clippers are under investigation by the Justice Department – it is meaningful that he chose the Raptors over big-market championship contenders like Miami, Minnesota, and Detroit. It’s also important that he proclaimed his desire to retire a Raptor before signing a two-year, $115m extension with the franchise. “He deserves to have his jersey retired somewhere,” says Lou. “But due to the circumstances of his career, he kind of was a player without a home.”

Leonard now has a chance to rewrite his complicated legacy with a familiar franchise. Leading the Raptors back to anywhere near the promised land would ensure him a jersey retirement ceremony, a first-ballot Hall of Fame induction, and Canadian sports immortality.

The Raptors, meanwhile, aren’t just getting an upgrade at the wing position; they are getting an all-time great coming off one of the best seasons of his career – an American superstar who experienced all the small cultural discomforts of playing in Toronto and still had such positive memories of the fans, organization, and city that he chose to return to.

“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,” says diehard Raptors fan Imman Adan. “But I definitely think him coming back cements Toronto’s legacy.”

It’s complicated, of course. It always will be so long as the Raptors are the lone NBA franchise outside of the United States. But 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.