TORONTO — This time a year ago, there was a sense that change was coming to the Toronto Raptors.
It wasn’t yet 100 per cent clear that the Masai Ujiri era was coming to an end after franchise-defining 13-year run where the Raptors won often and won big. The longtime executive was on the job in Chicago at the NBA pre-draft camp and represented the Raptors at the draft lottery, hoping they would jump from seventh to top four, and maybe all the way to No. 1 and be in position to draft Cooper Flagg.
Instead, the Raptors slipped to ninth and the Dallas Mavericks jumped from 12th to first and got Flagg. Soon after, Ujiri was sending signals privately that his time with the Raptors could be coming to a close, although publicly he pushed forward.
But the morning after the 2025 draft — only hours after Ujiri was on the phone congratulating Collin Murray-Boyles on joining the Raptors as the ninth-overall pick — Ujiri and the Raptors parted ways, ending a largely successful tenure and ushering a new era for a team that had been so closely associated with him as its public face.
There is much less uncertainly around the Raptors at this point in time. Continuity will be the order of the day.
It’s expected that both general manager Bobby Webster and head coach Darko Rajakovic will be offered contract extensions in the coming weeks, Sportsnet has learned. Each of them have another year left on their current deal.
As one well-placed source put it: “You don’t have your head coach and general manager head into the final year of their contracts as lame ducks, not after a playoff year.”
As another said: “It will happen when it happens,” referring specifically to Webster, “but it will happen.”
The timing, length and any other details related to an agreement with Webster are still to be determined as there have yet to be formal discussions with MLSE beyond a mutual understanding that there is a deal to be had. New terms with Rajakovic — who had a year added to his initial three-year deal in the second half of the 2024-25 season — will likely be Webster’s call.
But there is some urgency to the matter. With Ujiri being introduced on Tuesday as president’s job with the Dallas Mavericks, the NBA gossip sphere was abuzz with how, when and with whom he would fill out his front office.
At least one source speculated that he might try to hire Webster as his general manager in Dallas. Multiple sources I spoke with ruled that out almost instantly, on two grounds. One, now having had his own team to run, it’s unlikely stepping back to a supporting role would be something the current Raptors general manager would want to do, and two, the Raptors wouldn’t let Webster go.
“He [Webster] is the captain of his own ship here,” said one source.
But another possibility — maybe even likelihood — is that Ujiri could look to reunite with other members of the highly respected talent evaluation staff that he brought to Toronto and worked with for more than a decade.
Foremost among them is Raptors assistant general manager Dan Tolzman, the highly regarded player personnel expert whose relationship with Ujiri goes back to their days with the Denver Nuggets. Tolzman was one of Ujiri’s first hires — as director of scouting — when Ujiri left Denver to join the Raptors in 2013.
Tolzman helped lay the ground work for the Raptors acquiring Norm Powell (26th in 2015), Delon Wright (20th in 2015), Jakob Poeltl (ninth in 2016), Pascal Siakam (27th in 2016), Fred VanVleet (undrafted free agent in 2015) and OG Anunoby (23rd in 2017) as the foundation of the Raptors’ championship run. More recently, they can count Scottie Barnes (fourth in 2021), Ja’Kobe Walter (19th in 2024), Jamal Shead (45th in 2024) and Collin Murray-Boyles (ninth in 2025) among their success.
Since lateral moves between teams aren’t the norm in the NBA, were Tolzman to join the Mavericks it could well be as general manager. Beyond that, Patrick Engelbrecht and Curtis Crawford, the Raptors’ director of player personnel and global scouting, respectively, could also be targets given their track record and relationship with Ujiri.
That the broad strokes of a deal with Webster are still outstanding is largely circumstantial.
Pelley had signalled leading up to the NBA trade deadline that Webster was under no short-term urgency to prove himself, suggesting then that an extension was in the offing. Accordingly, Webster opted for a conservative approach, rather than spending the kind of draft capital required to pursue a big fish like Jaren Jackson Jr., the former Memphis Grizzlies big man who was very much on the Raptors’ radar before ultimately being traded to Utah.
As some may have noticed, Pelley has had his hands full sorting through myriad of Toronto Maple Leafs issues over the past few months. The underachieving NHL team has been on the front burner for most of the winter. But with a new executive tandem in John Chayka and Mats Sundin in place as of Monday and a very successful draft lottery now in the rear view, attention will turn to the Raptors, which Pelley held up as a model organization at the start of his Maple Leafs press conference on Monday.
Webster and Rajakovic will have a strong base to negotiate from, especially after a 46-win regular season, a fifth-place finish in the Eastern Conference and an impressive showing against the heavily favoured Cleveland Cavaliers in a first-round series that was pushed all the way to seven games — a collection of results that were at the peak of even the most optimistic projections coming out of training camp.
There was a sense that the 2025-26 season was almost an extended job interview for Webster and his basketball operations team, almost entirely holdovers from the Ujiri era.
“It was almost like, here’s your chance, let’s see how you handle it,” said one source.
Webster was in an odd position where most of the significant moves the Raptors have made — even dating back to the Kawhi Leonard deal that he was heavily involved in — were done under Ujiri’s umbrella. Even the decision to sign Poeltl to a three-year $84 million extension — the first major move the team undertook after Ujiri was let go — was well in the works before Webster was in charge.
But after a season that, at the very least, exceeded expectations internally and externally and with a young roster, a budding superstar in Barnes along with a full cachet of draft capital to work with, the Raptors are very much Webster’s team from here on in.
Three-point Grange — Webster post-season media availability edition:
RJ Barrett, a Raptor now and into the future. Maybe?
Barrett is coming off a career-best season and was arguably the Raptors second-best player in the playoff series against the Cavaliers, averaging 24.1 points, seven rebounds and four assists with an effective field goal percentage of 54.2, all improvements on his regular season totals.
Barrett is entering the final year of his contract, will earn $29.7 million next season, is extension eligible. As well, the 25-year-old Mississauga, Ont., resident made clear that his overwhelming preference was to re-sign with the Raptors and play the rest of his career in his hometown.
It all seems like a slam dunk to re-sign Barrett, but nothing with the Raptors is as clear as that given the team’s long-term salary commitments to Immanuel Quickley, Poeltl and — to a lesser extent — Brandon Ingram, who has one more year and a playoff option left on his deal. In that mix, Barrett’s deal might be the Raptors most useful trade asset.
When asked about Barrett’s status going forward, Webster kept in vague. Read into that what you will: “I think you always knew that [Barrett] was going to play a big, physical style of basketball. That was in full display, him getting to the paint, him getting to the rim. He had a little bit of a tough stretch going through some injuries. But I think he got back to full health and you saw that in the playoffs.”
And as for a new contract?
“We’re gonna keep all those conversations private. Spoke to RJ at the end of the season and spoke to him throughout the season. I think the best part is he is under contract, so that decision can also be at the end of [next] season.”
Big moves, little moves, no moves?
Webster said that, at the trade deadline, he didn’t feel like the time was right to cash any of its seven future first-round picks in a ‘win-now’ type move. It didn’t sound like the Raptors’ playoff run had moved him too far from that opinion as the off-season approaches: “Listen, our philosophy here has always been getting two-way players. I think I said this summer we’re in talent-acquisition [mode]. We still need more better players. There will be a time where it feels like, OK, this specific piece is what puts us over the top. But no, I think this summer will — whether it’s the draft or free agency or trades — just be looking at, the best two-way players available.”
The most significant pending Raptors free agent is big man Sandro Mamukelashvili who played well enough in his first opportunity as an NBA rotation player to easily exceed the value of his $2.8-million player option. His shooting off the bench (38.9 per cent from three) and easy locker-room fit have made him someone the Raptors would love to keep, but as their payroll stands now they are probably limited to something in the $6 million range without tipping over into the luxury tax. That might not be enough given his potential market, unless of course the Raptors did some roster juggling.
“We’ve been looking for that stretch big for a number of years, and so to see it with the bench, but also, I think sometimes with the starters, was nice to see. And then this summer? Listen, we’ll talk to his reps. We’ll talk to Mamu, who I think he obviously wants to be here. There’s probably financial realities of the NBA (but) we’ll do everything we can to retain him.”
