Bobby Webster didn’t speak the quiet part out loud, but he spoke volumes, regardless.
In his first extended comments since reacquiring Kawhi Leonard, the Toronto Raptors general manager avoided any ‘championship or bust’ proclamations, but with training camp about to open, he acknowledged that the bar for the current roster is considerably higher than it was a year ago.
“If I think back to last year, I sat here and I said, ‘the most important thing for this group (is) can we compete every night? Will we compete for 48 minutes?” Webster said at a media conference at the Raptors practice facility Thursday morning. “And I felt comfortable (that) group had a lot of fight, and I think that's probably what you saw play out over the course of the season.”
It worked out better than most expected as the Raptors jumped from 30 wins in 2024-25 to 46 wins and a fifth seed in the East in 2025-26 before falling to the favoured Cleveland Cavaliers in seven games in the first round of the playoffs.
But then this past summer Webster acquired Leonard, a 35-year-old coming off an all-NBA season and a player who will forever be recognized in Toronto as the driving force behind the team’s 2019 NBA championship.
Webster didn’t want to put a specific label on the goals or expectations for a team whose most accomplished player is now in his mid-30s and whose projected starting lineup takes up 105 per cent of the salary cap. But he allowed that yes, they are considerably higher, as they should be.
“I think the expectation this year is, you know, can we win every night? Does this group go into every night thinking that we're the better team? (That) we have a chance to win this game,” Webster said. “And so I think that's sort of how I view this group, which is they're going to be competitive, they're going to fight, and now they have the belief that they'll win.”
He added that if the Raptors need to bolster their lineup even further, that’s an option as well.
“I think we have a first-round pick in each of the next four years. That's probably important to note … if we want to go for it, we still can go for it,” Webster said. “Maybe that's the distinction — (this was) just a bit of a swing — but there's definitely more left on the bone."
But Webster cautioned against a straight-line comparison to the last time Leonard joined the Raptors, when he was acquired from the San Antonio Spurs.
That move was risky because Leonard had only played nine games due to injury the season before and had a clear preference to return to Southern California as soon as possible. There were concerns about whether Leonard would even report to Toronto. There was a one-and-done feel to the entire undertaking.
But everything worked out perfectly as Leonard was the ideal piece to add to a veteran, perennial playoff team trying to get over the hump. He played some of the best basketball of his career; the Raptors were able to hold a championship parade and then — as expected — Leonard signed with the Los Angeles Clippers in free agency.
Seven years later, there are similarities — mainly that Webster pulled off a somewhat risky trade to bring Leonard to Toronto, this time from the Clippers — but also significant differences.
This version of the Raptors is still a relatively young team early on its upward trajectory. And now Leonard is coming here by choice, rather than against his wishes, and perhaps happy to escape the Clippers after his seven seasons there ended in unmet expectations and controversy.
And while he just turned 35 and is starting his 15th season, the plan is that the Raptors with Leonard in the fold will get more than one chance to see how far he can take them, with Raptors two-time all-star Scottie Barnes doing his share of the heavy lifting as well.
“I think the biggest thing when we first agreed to the trade, in speaking to Kawhi's rep, is he didn't want this to be a short-term thing,” Webster said of Leonard signing a two-year, $115 million extension Wednesday that takes him through the 2028-29 season. “He wanted to stay here for a while, and I think that's probably what people hopefully took away from the extension was we want to have a window here, whether it's two years, three years or beyond that, where we're able to compete (and) put together a team that is worthy of competing for a title, and I think that's sort of the goal.”
A lot of things will have to go right for that even to be a possibility. Perhaps the biggest variable among them is Leonard’s health. The veteran has missed 44 per cent of his team’s games over the last nine seasons due to injury. But he’s coming off a 65-game season, and Webster is hopeful that’s a trend, rather than an exception.
Leonard had played just nine games the season before the Raptors acquired him in 2018, but with a careful protocol of rest and recovery — which became known as ‘load management’ — Leonard played 60 games in the regular season for Toronto and led the NBA in minutes played during the post-season.
Even though Leonard is eight years older now, Webster believes his injury risk can be properly managed, though he didn’t want to speculate on whether or not ‘load management’ was going to be part of Leonard’s protocol this time around.
Webster allowed that the continued presence of Alex McKechnie, the Raptors vice-president of player health and performance, should be an advantage the Raptors have, given that he was instrumental in keeping Leonard healthy in 2018-19.
“I think there's going to be so many times where we're going to be tempted to sort of compare this to 2019,” Webster said. “I think probably we need to focus mainly on moving forward, but I do think it’s an interesting distinction: by and large, (Leonard) was healthy last year. Obviously, the goal is to keep him healthy, but it's also only September 24th, so I think as we move forward, we'll have a better sense. But I think the biggest thing is he's coming off a healthy season.
“… I think Kawhi's health — like any player — we're going to have an extra eye, an extra hand in looking after him, and so Alex is huge in that respect.”
Leonard’s health may be the biggest single variable in whether the efforts made to trade for him a second time pay off or not.
But even if Webster tried to shy away from any talk of banners or specific goals he has for a newly configured team that has thrust itself into conversation as a contender in the Eastern Conference, the conclusions are self-evident: Last season the Raptors were expected to be competitive. This year they are expected to win.
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