The reacquisition of Kawhi Leonard brings back memories of the 2018-19 season for the Toronto Raptors and their fans.
That déjà vu was on full display Tuesday night when Leonard made his first appearance as a Raptor in more than seven years and scored an effortless 21 points in a blowout win over the New York Knicks.
But according to general manager Bobby Webster, there aren’t many similarities between the trade that first brought him to Toronto in 2018 and the deal that went down this past summer to bring him back.
“I do think it’s different. I think there’s going to be so many comparisons to 2019 and for obvious reasons. I think for a couple of important reasons, it’s a little different is he signed the extension,” Webster told TSN’s Kate Beirness in a wide-ranging interview posted to TSN.ca Wednesday.
“We all knew last time coming in, it was in many ways a one-shot deal. And I think this time is, we feel like we have a bit of a bigger window.”
By the end of the 2018 season, the Raptors has made the playoffs five years in a row but were eliminated by LeBron James and the Cleveland Cavaliers in three straight seasons. It was clear they needed a piece to get over the hump, which Leonard proved to be when he won Finals MVP for delivering the Raptors their first ever title.
This time, the Raptors are a team on the rise, having taken a massive leap forward in 2025-26 by returning to the playoffs for the first time in four years. With a two-year contract extension already signed, Webster sees Leonard as more of a long-term fixture and someone the team’s young core can grow alongside.
“At the same time, and people will talk to Kawhi and get, you know, he’s matured. And so, I think he has a different perspective, and I think he’s coming in with a, ‘I want to help and integrate into what we’ve already established here.’”
Webster said taking care of Leonard’s future beyond this season was “huge” and factored heavily into the decision to bring him back.
“To get him locked up, but also to understand his mindset, which is I want to come here. I want to finish my career here. I want to help the young players, the city, the fans, the country meant a lot to me. And so, I think that was all part of the package.”
Webster revealed that he and the Raps had kept tabs on Leonard’s availability during his time in Los Angeles that past few years and received a call from the Clippers just before the June 23 NBA Draft indicating they might be open to a trade.
Webster said he and the Raptors did their due diligence on Leonard, who at the time was under investigation alongside the Clippers by the NBA for possible salary cap circumvention resulting from an investigation from journalist Pablo Torre. And while the deal between Toronto and L.A. sat in limbo for months after it was agreed to, Webster said he was pretty sure things would ultimately work out.
“You know, I was confident. I wouldn’t have sort of engaged as much with the Clippers if I didn’t feel like we could get to the finish line.”
But that didn’t mean he was certain.
“There’s always concern, right? Life isn’t black and white, and I think you have to live in these gray areas a bit, and I think that’s the risk you have to take in any part of this business. And so, of course, there’s probably some concern at some point over the summer. But I always come back to we were confident that the end result would be this,” he said.
The Clippers and owner Steve Ballmer were heavily punished as a result of the investigation, but Leonard only received a modest $700,000 fine in comparison to his $56.1 million salary for 2026-27. Nearly two weeks after the punishment was announced, the deal sending Leonard back to Toronto in exchange for Brandon Ingram, Gradey Dick, two first-round picks, two second-rounders and a pick swap became official.
Leonard said at media day last month he wanted to put the saga behind him and focus on the season. Part of how things go this year will depend on his health.
The Raptors kept Leonard healthy through the 2018-19 season, which played a huge part in their run through the playoffs en route to the title. Webster said keeping Leonard – now 35 – healthy remains a delicate process.
“We honestly will take it day-by-day, and then we’ll take it week-by-week, and then we’ll figure out over the course of the season. I think that’s the only way to sort of proceed, sort of intelligently, but also not create expectations for him. Not create expectations publicly, but keep that really secure and have him trust the staff.”
Leonard played 65 games last season with the Clippers while averaging a career-best 27.9 points per game.