Kawhi Leonard Returns to Toronto: A New Era for the Raptors

Fred VanVleet has seen Toronto at its peak. He helped build it. So when he looks at Kawhi Leonard walking back through the Raptors’ doors, he doesn’t see nostalgia. He sees danger for the rest of the Eastern Conference.

At Kyle Lowry’s block party, amid the music and memories, VanVleet didn’t bother dressing it up.

“I mean, listen, they didn’t get worse,” said the former Raptors guard, now with the Houston Rockets. “It didn’t get worse.

“I’m excited for the city. I’m excited for the organization. It’s good to see [Kawhi Leonard] back and yeah, they’ll be a damn good team, especially in the East. They’re going to be a tough out.”

For a man who lived through the most transformative year in Raptors history, that carries weight.

The Return of the Reluctant Superstar

Leonard’s relationship with Toronto has always been complicated, and that’s putting it kindly. VanVleet has never hidden the truth about that 2018–19 season: Kawhi did not arrive as a willing savior.

“He said it from day one, I’m not staying here,” VanVleet recalled on the Hello and Welcome podcast. “So, from day one, he said, ‘I don’t know why they traded for me. I don’t want to be here. I’m not staying here.’”

Toronto tried everything. The franchise rolled out its best pitch. The city wrapped its arms around him.

“Now, Toronto put their best bid in, man. The city bowed down as we’ve never seen before, man,” VanVleet said. “And so yes, as for us regular people, we can look at it and say, man, how could you leave that? But his mind was made up, man. Kawhi is Kawhi.”

And still, with one foot mentally out the door, Leonard delivered the greatest season the franchise has ever seen. He treated that year like a business trip and left with a championship briefcase.

VanVleet has long credited that run with changing lives in that locker room — his included. The title cemented his reputation, helped launch the major contracts that followed, and permanently altered the trajectory of his career.

Raptors Go All-In Again

Now Toronto has gone back to the well.

To pry Leonard away from the Los Angeles Clippers, the Raptors paid a steep, unmistakably win-now price: Brandon Ingram, guard Gradey Dick, two unprotected first-round picks in 2031 and 2033, a 2027 pick swap, and two future second-rounders.

That is not a nostalgia trade. That is a franchise betting that a 35-year-old, two-time Finals MVP can still tilt a conference.

Leonard returns to a very different Raptors team. The old core is gone. In its place stands a retooled, younger group built around rising star Scottie Barnes. The dynamic is new. The stakes feel familiar.

VanVleet, watching from afar, clearly believes Leonard still changes the math in the East. “They’ll be a damn good team,” he said. “They’re going to be a tough out.” It’s the kind of line that sounds like cliché until you remember who’s saying it and what he’s seen.

Inside the Championship Locker Room

VanVleet’s respect for Leonard runs deeper than rings and banners. It comes from the day-to-day grind, the private moments that rarely leave a locker room.

“Kawhi [Leonard] changed my view on a lot of shi*t,” VanVleet admitted on the podcast.

Then he shared one story that stopped him in his tracks.

“There was one thing in particular that I overheard and he didn’t say it to me, I just overheard it and it was a conversation that was being had. And the sentiment of the conversation, because I ain’t going to quote nobody, but the sentiment of the conversation was when we won the championship about all that sh*t is like, ‘I’m better than Kobe.’”

VanVleet’s reaction was instant.

“Right? I had the same reaction because Kobe is my man. Kobe, that’s it for me. That’s as good as it gets for me as a little kid up into a man, my eyes, what I seen.”

It’s a startling sentiment, even framed as overheard locker-room talk. But it underlines the level of self-belief that fueled Leonard’s historic postseason. Two titles. Two Finals MVPs. Two different franchises. The résumé gives him the right to at least enter that kind of conversation, even if most fans will never accept it.

For VanVleet, that mindset was an education. Leonard didn’t just bring a superstar’s game to Toronto. He brought a superstar’s conviction.

Now he brings it back to a city that once “bowed down” for him and a franchise that has again pushed its chips to the middle of the table. Leonard is older. The roster is younger. The East is deeper.

But if Kawhi is still Kawhi, how many teams are really ready to see Toronto in a seven-game series?