It took longer than anticipated, but Bobby Webster always believed Kawhi Leonard would be reunited with the Toronto Raptors.
Toronto acquired Leonard from the Los Angeles Clippers in June. But the deal wasn’t finalized until earlier this month after the NBA investigated Leonard and the Clippers for salary-cap circumvention.
On Wednesday, Leonard signed a two-year extension with Toronto, returning to the franchise he helped win its only NBA title in 2019.
“Listen, with any deal — free agent, trade — you have to do a ton of due diligence (and) we did our due diligence, we had the conversations we needed to have,” Webster, Toronto’s general manager and executive vice-president, told reporters Thursday at the OVO Athletic Centre. “We had confidence, I think that’s probably the biggest thing, we had confidence that eventually the deal would go through.
“We had to be incredibly patient and there were a lot 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.”
As per team policy, the financial details of the deal were not disclosed Wednesday. However, several media outlets reported Leonard and the Raptors had agreed to a two-year, US$115-million contract extension.
The extension reportedly includes a player option for the 2028-29 season. But it comes in under the maximum $126.6 million Leonard was eligible for.
Leonard, 35, will complete a three-year, $149.5-million deal this season. Then the extension will kick in.
The six-foot-six, 225-pound Leonard averaged 27.9 points, 6.3 rebounds, 3.6 assists, 1.9 steals and 0.4 blocks over 65 regular-season games last year with the Clippers. He has averaged 20.7 points, 6.4 rebounds, 3.1 assists, 1.7 steals, and 31.8 minutes over 14 NBA seasons with the San Antonio Spurs (2011-18), Toronto (2018-19) and Clippers (2019-26).
Toronto sent all-star forward Brandon Ingram, guard Gradey Dick, unprotected first-round selections in 2031 and 2033, a 2027 first-round pick swap and two second-round picks to LA. But Leonard, a two-time NBA champion, is a seven-time league all-star, a seven-time All-NBA selection and a seven-time All-Defensive Team honouree.
Leonard has been named both an NBA Finals MVP and NBA Defensive Player of the Year on two occasions.
Toronto first acquired Leonard on July 18, 2018, from San Antonio after he played just nine games with the Spurs the year before. But Leonard played 60 regular-season contests with the Raptors before guiding the franchise to its first — and so far only — NBA title.
On July 10, 2019, Leonard signed with the hometown Clippers as a free agent.
But unlike 2018 when there were health concerns surrounding Leonard, Webster said no such worries exist this time around.
“I think there’s going to be so many times that we’re going to be tempted to, sort of, compare this to ’19,” Webster said. “I think we probably need to focus mainly on moving forward.
“Obviously the goal is to keep him healthy. But it’s also Sept. 24 and 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.”
Kyle Lowry, right, speaks with Kawhi Leonard after a press conference in which Lowry signed a one-day contract to retire as a Toronto Raptor, in Toronto, on Tuesday, July 7, 2026.THE CANADIAN PRESS/Chris Young
Toronto finished 46-36 last season, the same as Atlanta, but secured the Eastern Conference’s fifth seed after having swept the Hawks 4-0. The Raptors earned their first playoff berth since the 2021-22 season but lost their opening-round series to the Cleveland Cavaliers in seven games.
“We’re not going to get into expectations,” Webster said. “If I think back to last year, I sat here and said probably the most important thing for this group was, ‘Can we compete every night? Will we compete for 48 minutes,’ and I felt comfortable saying that.
“I think the expectation this year is that, ‘Can we win every night? Does this group go into every night thinking that we’re the better team? We have a chance to win this game.’ 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 the belief that they’ll win.”
Webster said Leonard’s extension won’t prevent Toronto from making future moves to strengthen another championship run. It also won’t handcuff the Raptors from keeping their own.
And that would include Canadian RJ Barrett, who’s entering the final year of his contract. The six-foot-six, 214-pound Barrett made 57 starts with Toronto last season, averaging 19.3 points, 5.3 rebounds and 3.3 assists per game.
“Ownership has been incredibly supportive,” Webster said. “So any time financially we want to make a go-for, they’re very supportive.”
Webster said there are many ways Leonard will help the Raptors this season.
“He has a really, really high level of work ethic and excellence,” he said. “I think you don’t continue to play at the age of 35 if you’re not doing that.
“Those type of habits, I think, are probably what will rub off the most.”
This report by The Canadian Press was first published Sept. 24, 2026.
By Dan Ralph | Copyright 2026, The Canadian Press. All rights reserved.