When Kawhi Leonard became a Toronto Raptor for the first time in the summer of 2018, he looked shellshocked. 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. 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. 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).
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. 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.
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