The Toronto Raptors officially tip off on the 2026-27 season Wednesday night against the Chicago Bulls, and the excitement around the team is palpable following the addition of Kawhi Leonard to a talented young core.
After making their way back to the playoffs last year for the first time since tearing down the remaining pieces from the 2019 championship team, the Raptors pushed the Cleveland Cavaliers to the brink in a hard-fought first-round series before running out of gas in the second half of Game 7.
Over the off-season, Raptors general manager Bobby Webster took advantage of a precarious situation brewing between the NBA and the Los Angeles Clippers to bring Leonard back to Toronto, reuniting the two for the first time since their championship triumph in 2019.
Despite carrying an extensive injury history and coming off a cap circumvention scandal that sent shockwaves through the league, Leonard’s presence north of the border has immediately vaulted the team back into the conversation as contenders in what is expected to be a highly-competitive Eastern Conference this season.
“After seven years, we all grow up and gain perspective,” Webster said of Leonard in a Wednesday morning appearance on TSN1050’s First Up. “I think for those who have kids, he had a child born in Toronto so there’s probably all of that. And then there’s obviously good feelings and good vibes, I’m sure, from memories of being here.
“This time, the circumstances around him arriving in Toronto were much different, the circumstances around him wanting to stay here were different. I think that speaks to his perspective and his growth.”
The trade over the summer marked the second time that Webster has pulled off a deal to bring Leonard to Toronto after he and then-president of basketball operations Masai Ujiri did so ahead of the 2019 season in an attempt to shake up the roster and finally get over the hump in the playoffs.
Immediately following the deal, rumours began to surface over Leonard’s lack of interest in playing for the Raptors. The Los Angeles native was set for free agency the following summer and offered no guarantees that he would even consider signing an extension in Toronto.
With all of the speculation surrounding his future, Leonard would make the the most of his time in Toronto with an All-Star nod, an All-NBA second team selection, a Larry O’Brien Trophy, and an NBA Finals MVP for one of the most dominant postseason performances in recent memory.
Following the championship festivities, Leonard would bolt back home to team up with Paul George on the Clippers. Since then, both he and the Raptors have never gotten back to the heights they reached together seven years ago.
He now returns to a Toronto team with Scottie Barnes as their star and Darko Rajakovic as head coach, but with the same fanbase holding aspirations of competing for a championship – something Leonard is no stranger to.
“We know this is a completely different team, there’s not even one player from that team on the current one,” Webster said. “So you want to sort of balance the line between having nostalgia for the past but also pushing forward, and this group of guys with Scottie [Barnes], [Immanuel] Quickley, RJ [Barrett] and the whole starting group there with Jakob [Poeltl] - they’re going to push in their own way.
“They all want to win and they all want to prove themselves in this league.”
In his lone season with the Raptors, Leonard routinely sat out back-to-backs and played in just 60 games during the regular season in a deliberate effort by the team’s training staff, led by vice president of player health and performance Alex McKechnie, to keep their star player healthy for the eventual playoff run.
Leonard has not eclipsed the 68-game mark in over a decade, and is now seven years older than he was when he first arrived in Toronto. So what can the Raptors expect to get out of him this time around?
“I think it’s different,” Webster said. “28 vs. 35, everybody’s bodies feel different. On the positive side of things, last time we acquired him he was coming off a season where he was injured and he played nine games.
“This year, he’s coming off of a healthy season, so I think we’re starting from a good point. The summer was, as we all know, a little bit uneven with the uncertainty around the trade, but he’s fully healthy going into the season, and knock on wood we keep him that way.”
With Leonard in Toronto for at least the next two seasons to pair with Barnes, the Raptors now boast one of the more formidable duos in the Association.
There are a number of similarities between the lengthy two-way wings, and Webster is hoping that Leonard’s championship DNA can rub off on him during their time together in Toronto.
“We want to compete every night, but now we want to win every night. I think Kawhi, over the course of his 14-year career, he’s been able to do that. So for Scottie, I think that growth, his game – the Cleveland series showed two-way basketball – when he’s really locked in, he can be dominant on both ends, so now let’s do that every night.
Let’s learn how to win in the clutch, let’s learn how to win down the stretch and it’s something that Kawhi will definitely help him with.”
The Raptors open their season with a home date against the Bulls, before hitting the road for meetings against the new-look Washington Wizards and the Minnesota Timberwolves to close out the first week of the year.