A key contract extension is expected after the NBA trade deadline

With the NBA trade deadline approaching in less than a month, Toronto Raptors is expected to finalize a key contract extension within the franchise after the Feb. 5 deadline.

Sportsnet’s Michael Grange reported Monday that the Raptors and basketball team president Bobby Webster engaged in substantive conversations regarding a multi-year extension to his current contract, with negotiations expected to accelerate after the deadline.

“According to multiple sources, Webster and the Raptors have been in significant discussions about a multi-year extension to his current contract, and discussions are expected 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 developed during his first season overseeing basketball operations.

“There’s a really good atmosphere,” one source said. “Everybody’s comfortable with each other. Communication is good. It seems like there’s a big view of the whole thing. It’s kind of an (old-school) approach to doing business with management. There’s a lot of runway and there’s no rush. Everything has cooled (from 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 last summer.”

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

“It’s all about the long term,” the source said. “There was pressure early on with the proof of concept — could Scotty Barnes make the move? How would Brandon Ingram fit in? — but that’s in any business.”

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

Webster assumed the franchise’s top basketball role last summer after an executive search led by MLSE President and CEO Keith Pelley, who ultimately decided to retain Webster instead of bringing in an outside replacement for Ujiri. Although Webster did not receive a new title, he was entrusted with full oversight of basketball.

According to Grange, there was an initial period of evaluation as Webster settled into the role, but several factors helped build trust throughout the organization. That included Toronto’s performance in the Summer League, the Raptors 905’s strong performance in the G League and the Raptors’ overall play in the first half of the NBA season.

When asked directly if Webster’s contract status could factor into decisions before the trade deadline, Pelley dismissed the idea.

“There’s no pressure at the trade deadline or his contract,” Pelley said. “And he’s 100 percent aware of that. The team is moving in the right direction and I’m confident that Bobby will make the right moves, at the right time, to make us better. This team under Bobby’s leadership will compete for a championship.”

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