Kawhi Leonard is a championship-caliber player capable of changing the fortunes of a team single-handedly, and there was no better example than the 2018–19 season. Traded to the Toronto Raptors, he immediately led them to an NBA Championship. It felt like the dawn of a potential new dynasty, but Leonard had no interest in staying a moment longer.
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Leonard, in the free agency following the Raptors’ victory over the Warriors in the Finals, was tempted to move back to California, especially Los Angeles. Ultimately, he signed with the Clippers, setting off a chain reaction that saw the ambitious franchise make the (in hindsight) disastrous decision to sign Paul George.
Raptors fans, meanwhile, felt slighted by Kawhi not re-signing with the team at the time. But his former teammate in Toronto, Fred VanVleet, recently revealed that it was always going to be the outcome.
“He said it from day one, ‘I’m not staying here,’” VanVleet said on Hello and Welcome. “Toronto put their best bid in. The city bowed down like we’ve never seen before… But his mind was made up. Kawhi is Kawhi. I thank him eternally for helping us win a championship.”
Leonard ended up being a mercenary for the Raptors that season. He led the team in almost all major statistical categories and delivered clutch moments throughout the playoffs. It nearly changed his mind about wanting to leave.
“He (Kawhi) said it from day one… I’m not staying here.” – @FredVanVleet pic.twitter.com/zwK8oDehz6
— hello and welcome (@hellowelcomepod) December 15, 2025
In fact, Kawhi was very upfront about his approach to free agency that year, revealing that he came close to re-signing with Toronto.
“I was very close. Real close. But when [the Clippers] presented the opportunity of playing with Paul, it was easy, it was a yes. I said let’s get it going,” Leonard told Rachel Nichols at the time.
Kawhi on how close he was to choosing the Lakers or Raptors instead of the Clippers:
“I was very close. Real close. But when [the Clippers] presented the opportunity of playing with Paul, it was easy, it was a yes. I said let’s get it going.”— Rachel Nichols (@Rachel__Nichols) July 24, 2019
When George and Kawhi teamed up that offseason, many were excited to see what they could accomplish. However, both players struggled to stay on the court due to injuries, and they ultimately failed to achieve much together.
George was traded to Philadelphia in 2023, while the Clippers began relying on a new superstar in James Harden. Still, a championship continues to elude them.
What’s interesting, though, is that years later, Leonard was reportedly investigated for salary-cap circumvention related to his Clippers contract. He allegedly held a no-show job connected to the team, allowing him to receive additional money off the books. According to sources, Kawhi and his agent had demanded a similar arrangement from the Raptors at the time.
Ultimately, the asking price was too high for Toronto to agree to, and Leonard left for Los Angeles. Since then, the Raptors have made the playoffs only twice, though they did manage to return to the Eastern Conference Semifinals just one season after Kawhi’s departure.
