Growing confidence Masai Ujiri will remain with Raptors?

Raptors president of basketball operations Masai Ujiri isn’t under contract with the franchise beyond the 2020-21 season, but there’s growing confidence that the two sides will be able to complete a new deal that extends Ujiri’s time in Toronto, says Michael Grange of Sportsnet.ca.

“Masai doesn’t share a lot; he’s very private and strategic in his own way,” a source close to Maple Leaf Sports and Entertainment, the Raptors’ ownership group, told Grange. “But if you were asking, ‘Are they going to sign Masai?’ I would put it at 95% yes.”

Grange cautions that the 95% estimate is just a prediction from one plugged-in insider, but says there have been other positive signals as of late. According to Grange, Ujiri – who has ceded some front-office responsibilities to general manager Bobby Webster – has seemed more involved, engaged and forward-looking in recent weeks. One source says Ujiri has been more active in communicating with players, both in person and via text.

“We talked about winning and winning another title with the Raptors,” one agent who recently met with Ujiri told Grange. "He seems like he’s in a really good place.”

Grange also notes that no front-office jobs in marquee markets such as Los Angeles and New York seem likely to open this offseason, considering how well those teams have performed. The Wizards have reportedly had interest in Ujiri in the past, but it’s unclear whether they’ll be looking to make any front-office changes this spring or if they’d be willing to outbid Toronto for the former Executive of the Year.

There has been some speculation around the league that Ujiri might eventually wind up in Seattle if the league approves a new franchise, as Marc Stein of the New York Times reported last month. Longtime sports executive Tim Leiweke, who hired Ujiri as Toronto’s executive vice president and GM in 2013, is involved in Seattle’s expansion efforts.

However, as Grange points out, while the NBA has seemed more open to expansion as of late, it still appears to be multiple years away, and it seems unlikely that Ujiri would take a hiatus while waiting for such an opportunity. Even if running an expansion franchise is something that appeals to him, he and the Raptors might end up working out a shorter-term contract that gives him some flexibility, Grange writes.

“They’re going to try to sign him for as long as they reasonably can, (but) if they have to sign him for less, they’ll sign him for less,” the source close to MLSE told Sportsnet. “They don’t have a lot of leverage. They want him. If he wants (a shorter deal) what are they going to say, no?”