It was scarcely believable when rumours first emerged in mid-June that the Toronto Raptors may be on a collision course with Kawhi Leonard — the man who led the franchise to its first and only NBA title.
Leonard had made the unprecedented free agent decision of leaving the Raptors on the heels of winning a title and Finals MVP for the Los Angeles Clippers, only to now return after arguably the most intense investigation in league history and unquestionably the most severely punished illegal actions ever seen.
He was here for a good time back in 2018-19, but the “Fun Guy” has seen that the grass wasn’t greener on the other side and intends on sticking around for a long time now. It was announced on Wednesday that Leonard has committed to a two-year extension worth a reported $115 million, approximately $11 million less than the maximum he could have signed for.
“I think the biggest thing when we first agreed to the trade, speaking to Kawhi and his rep is, he didn’t want this to be a short-term thing,” Webster revealed. “He wanted to stay here for awhile and I think that’s probably what hopefully people took away from the extension.
“We want to have a window here whether it’s two, three, beyond that, where we’re able to compete, put together a team that is worthy of competing for a title.”
How the Raptors got Leonard back
Webster and the Raptors front office have made it part of their regular practice to keep tabs on players they feel can make a difference in taking this franchise to a championship level. Over the course of the last trade deadline and the early summer, Toronto was linked to the likes of Anthony Davis, Jaylen Brown and Jaren Jackson Jr.
The Clippers had started to go in a different direction last deadline, with a deal that sent veteran superstar James Harden to the Cleveland Cavaliers in exchange for 26-year-old Darius Garland. They also traded 2024-25 All-Defensive Team centre Ivica Zubac to the Indiana Pacers for 24-year-old Canadian Bennedict Mathurin — who since left in the summer.
Around the week of the draft, the Clippers reached out to the Raptors indicating that they were fully heading in a younger direction and were open to moving off Leonard’s $50.3 million contract for the 2026-27 as a result.
The Raptors GM and vice president was immediately excited by the potential opportunities, describing the “antennas” going up and ready to make something happen. Leonard was coming off a very healthy season, playing in 65 games and looked like one of the very best players in the game in averaging a career-high 27.9 points to go along with 6.4 rebounds, 3.6 assists, and 1.9 steals.
Despite Leonard’s injury concerns having played in just 60 percent of regular season over the course of his seven-year Clippers tenure, the Raptors had confidence in his habits because of what they had seen in person as Leonard helped bring home a championship in the ‘2018-19 season.
“He has a really high level of work ethic and excellence,” Webster said. “You can see that from afar, players can see that when he’s working, pre-game with his diligence, post-game with his recovery, I think that’s what sticks with me about what was unique about him back then.
“You don’t continue to play at the age of 35 if you’re not doing that. Those type of habits are probably what will rub off the most.”
Webster attributed getting a deal over the line just before free agency in early July to his strong relationship with Clippers general manager Trent Redden, who has since taken over as president due to the incumbent Lawrence Frank’s suspension.
There was the agreement on June 30, but then came the waiting.
The waiting game bears fruit for Raptors
The biggest source of criticism that came Webster’s way stemmed from the Raptors electing to pause the trade on July 9. The league had informed the team that any possible punishment for Leonard stemming from the investigation into the Clippers for salary cap circumvention would have to be served even if he were relocated to Toronto.
Surely, that was something Webster would have known before hand so what would give him reason to pause. Webster didn’t divulge much in that regard, insisting that no new information emerged and that it was more a matter of dotting “I’s” and crossing “T’s” and that as long as Leonard was able to report to training camp, the wait was immaterial.
Webster maintained that the Raptors always had confidence that the deal would get over the line, but he did say he didn’t have much of a feel for whether Leonard’s current contract would be voided — the most significant punishment a player can incur for salary cap circumvention — and that the possibility of that happening shifted one way or another at any point.
“In reality, we just needed to make it to the end of September when Kawhi is here,” Webster said. “Maybe as uncomfortable and uncertain as it was in July and August, in reality the investigation just needed to finish by September.”
Winning time is back in Toronto
OAKLAND, CA – JUNE 13: Fred VanVleet, Kyle Lowry, Kawhi Leonard and Serge Ibaka of the Toronto Raptors (pictured L-R) celebrate an NBA Championship at the conclusion of Toronto’s 114-110 win over the Golden State Warriors in Game 6 of the 2019 NBA Finals on June 13, 2019 at Oracle Arena in Oakland, CA. (Photo by Daniel Gluskoter/Icon Sportswire via Getty Images)
When an NBA team acquires a player of Leonard’s pedigree, winning a championship immediately comes to the forefront.
Every player, every coach, every medical staff member and front office executive is on notice to maximize this window that will feature Leonard for at least his age 35, 36 and 37 seasons.
Are the Raptors ready to contend for a title coming off a 46-win season and a first-round seven-game series exit? Leonard certainly makes them better but there will need to be leaps across the board in what looks like a very stacked Eastern Conference this year.
The New York Knicks come in as defending champions, the Philadelphia 76ers added LeBron James and Jaylen Brown, while the Boston Celtics and Indiana Pacers are welcoming back Jayson Tatum and Tyrese Haliburton, respectively, from Achilles ruptures. The Detroit Pistons were the East’s top seed last year while the Cavs got better, too. There will be no shortage of challenges.
Webster, well aware of that, sent his own warning to the league that the Raptors may have another big trick up their sleeve.
“I think we’re a million over the tax, similar to last year you can see how it goes,” Webster said. “You can get under if you need to, you can also add to it if you felt like the team was in position.
“That was a big one, was if we wanna go for it we still can go for it. I think that’s the distinction, this is sort of a swing but there’s definitely more left on the bone.”