Toronto Raptors GM Bobby Webster speaks at a press conference.
Toronto Raptors GM Bobby Webster speaks at a press conference. Toronto Raptors/X
Rarely is a general manager’s season-opening media conference almost entirely centred around one player — but Kawhi Leonard isn’t just any player.
All but a handful of questions sent Bobby Webster’s way Thursday were about the slow-moving trade to bring the man who delivered a championship to Toronto back, or how much he still has left in the tank or how Leonard can change the fortunes of the current group.
Webster had long made it clear that the Raptors were looking to add an elite player to a roster led by all-world defender Scottie Barnes and when the Los Angeles Clippers called around the draft in June saying they were ready to talk, negotiations began.
While reminding several times that this isn’t the exact same situation as when Leonard first arrived in 2018-19 and attempting to temper expectations a bit, Webster made it clear everyone is thrilled to have him back.
“We were excited. We all have good memories and good feelings from 2018-19. But at the same time, you have to be honest with yourself about whether it makes sense at this point in time, at this juncture for this team and the development of this team,” Webster said. “But yeah, your antennae go up and you want to hear more.”
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So the two sides talked and, even when the Clippers and Leonard faced legal and NBA-issued penalties due to the cap circumvention scandal, leading the Raptors to pause the trade, there was still a sense from Toronto all along that it would eventually get done.
What did Webster say about the Clippers investigation?
“We did our due diligence. We had the conversations that we needed to have. We felt comfortable enough to proceed as much as you could with the deal. This was a really unique situation from all sides,” Webster understated.
“Do I know everything that happened? No, not from a factual standpoint. There are a lot of different parties involved, but we had confidence … We had to be incredibly patient. There were lots of twists and turns, but we wouldn’t have agreed to the deal if we didn’t have a level of confidence that we could get it done.”
And as we suggested back when the penalties against the Clippers and Leonard came down, there was no thought to re-opening the parameters of the deal, perhaps trying to hold the Clippers hostage. That’s just not how pro sports generally works.
“No. It gets back to the question about how this is a small industry that we all live in. You have your reputation, and I think that’s really important,” Webster said. “Putting aside what happened from June 30 onward, I think that felt secure to me and I think neither side would want to feel like the other side was doing something different.
“When you agree to a deal, you agree to the deal. That’s important — not just in this industry, but in any industry.”
Webster said the pause was fine as long as things were wrapped up by September, when the season neared. It was “risk tolerance” during the summer.
He said the NBA’s eventual settlement with the union (resulting in a $700,000 US fine for Leonard and the banning of his advisor and agent) “was probably what gave us assurance (that Leonard wouldn’t face further penalties).”
On Kawhi’s health and wealth
We asked Webster about how still having director of sports science Alex McKechnie, who spear-headed the infamous ‘load management’ campaign around Leonard during his previous time with the team, helped reassure him in bringing the two-time NBA Finals MVP back and give him a contract extension that will take him into his late 30s, despite his shaky health history.
“I think the familiarity that Kawhi had with the organization and the city, and the good feelings he’s had towards it, helps. Kawhi’s health, like any player’s, is going to require an extra eye and an extra hand in looking after him. Alex is huge in that respect, but the entire medical group is really important,” Webster said.
Leonard has played in at least 65 games in two of the past three seasons and was one of the eight best players in the league in 2025-26, which is different from the initial acquisition, when he only had played in nine games and it was unclear if he’d be able to get all the way back to full health.
“I think there’s going to be so many times where we’re going to be tempted to compare this to 2019. I think we probably need to focus mainly on moving forward,” Webster said. “I think the biggest thing is he’s coming off a healthy season.”
Webster also vouched for Leonard’s character, saying “From a person and a player, we’re really comfortable. There’s obviously curiosity to know what has happened since then, but we had those conversations and we felt comfortable. That gave us a lot of confidence to move forward with the deal.”
In it for long haul
At no point in 2018-19 did Leonard show any indication he was going to stick around longer than that season. That’s not the case now.
“The biggest thing when we first agreed to the trade, speaking to Kawhi and his rep, is that he didn’t want this to be a short-term thing,” Webster said. “He wanted to stay here for a while.
“I think that’s probably what people hopefully took away from the extension — we want to have a window here, whether it’s two, three years, or beyond that, where we’re able to compete and put together a team worthy of competing for a title. That’s the goal.”
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