Key Raptors contract extension expected after NBA trade deadline

As the NBA trade deadline approaches in less than a month, the Toronto Raptors are expected to finalize a key contract extension within the franchise following the Feb. 5 deadline.

Michael Grange of Sportsnet reported Monday that the Raptors and team president of basketball operations Bobby Webster have engaged in substantive talks regarding a multi-year extension to his current deal, with negotiations anticipated to accelerate after the deadline.

“According to multiple sources, Webster and the Raptors have had meaningful discussions on a multi-year extension to his current deal with talks expected to pick up after the trade deadline,” Grange reported.

Grange added that while several sources declined to speak on the record, there was consistency in how the relationship between Webster and the organization has developed during his first season overseeing basketball operations.

“There’s a really good vibe,” said one source. “Everyone is comfortable with each other. The communication is good. It seems like there is a big-picture view of the whole thing. It’s kind of (an) old-school approach to dealing with management. There’s a lot of runway, and no rush. Everything has cooled off (since the decision to part ways with former Raptors president Masai Ujiri last June). They’ve really come a long way, considering there was an executive search this past summer.”

Another source cited a long-term focus that has guided the organization through the transition.

“Everything is with a view to the long term,” the source said. “There was some pressure early on regarding proof-of-concept — Could Scottie Barnes take a step? How would Brandon Ingram fit? — but that’s there in every job.”

Bobby Webster’s trust with Raptors paves way for contract extension

Webster assumed the franchise’s top basketball role last summer following an executive search led by MLSE president and CEO Keith Pelley, who ultimately opted to retain Webster rather than bring in an external replacement for Ujiri. Although Webster did not receive a new title, he was entrusted with full basketball oversight.

According to Grange, there was an initial evaluation period as Webster settled into the role, but several factors helped solidify confidence across the organization. Those included Toronto’s performance at Summer League, a strong showing by Raptors 905 in the G League, and the Raptors’ overall play through the first half of the NBA season.

When asked directly whether Webster’s contract status could influence decisions ahead of the trade deadline, Pelley dismissed that notion.

“There is no pressure regarding the trade deadline or his contract,” Pelley said. “And he is 100 per cent aware of that. The team is moving in the right direction and I’m convinced that Bobby will make the right moves, at the right time, to make us better. This team under Bobby’s direction, will contend for championships.”

On the court, Toronto sits at 25–19, holding fourth place in the Eastern Conference despite a recent two-game losing streak that includes a 110–93 loss to the Los Angeles Lakers on Sunday night. The Raptors continue their five-game road trip Tuesday against the Golden State Warriors (25–19) at 10:00 p.m. ET, with Golden State recently losing Jimmy Butler III to a torn ACL suffered during a win over the Miami Heat.

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