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Opting for continuity, Raptors expected to offer extensions to Webster, Rajakovic

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06.05.2026

TORONTO — This time a year ago, there was a sense that change was coming to the Toronto Raptors. 

There was uncertainty. 

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.........

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