The dust has settled, folks, and it’s official: the Toronto Raptors have appointed their new head honcho to succeed the revered Masai Ujiri.
As many anticipated, this is an internal promotion, with General Manager Bobby Webster stepping up as “the team’s head of basketball operations,” as ESPN NBA Insider Shams Charania broke the news on X. In the process, Webster has also been able to reach a new long-term contract to keep him in Toronto.
While some might assume Webster’s new title is President of the Raptors, it has been clarified that he will simply remain GM, though he remains the team’s top decision-maker alongside MLSE ownership.
Raptors promote Bobby Webster, but can he learn from Masai Ujiri's slip-ups?
For the die-hard Raptors fans, seeing a familiar face they've come to know — and who many expected to eventually surpass Masai Ujiri — is likely a positive sign. Having that person step into the top position of Toronto's basketball operations has to feel like a good thing ... right?
Well, I won't be the one to tell Raptors Nation otherwise, but what I will say is that, even though I firmly believe Webster can establish his own sense of flair, culture, and influence as this new gig takes shape, there's a lingering thought (perhaps even a grave concern) that Bobby Webster might simply pick up right where Ujiri left off, especially in how he approaches building the roster and managing the team's finances.
It's no secret that while Ujiri had his ride-or-die supporters within the Raptors fanbase (the saying didn't go "In Masai We Trust" for nothing), he was also known for making some unconventional basketball decisions. In his later years with the franchise, he gained a reputation for sometimes going all-in on trading for mid-tier talent (something an ESPN list highlighted as the Raptors' biggest mistake of the 2020s) or for extending many unproven players to costly contracts. These choices have largely contributed to the current challenging salary cap situation the team faces.
I previously highlighted how this strategy — one that largely defies the new NBA trend of cautious spending and careful talent management — could potentially haunt the Raptors for years to come. But that's just playing devil's advocate to some extent. I wouldn't say the Raptors have no bright spots ahead. While some other basketball pundits and fans might see this internal promotion as a sign that the team isn't making a huge leap forward, that would overlook Bobby Webster's potential to thrive in a higher role.
I fully expect Webster to take this position very seriously, and I don't believe he's clueless—he's well aware of the ups and downs within the Raptors' current structure. I have faith that Webster will gradually shift toward a more cost-efficient strategy as a franchise leader, emphasizing effective team-building and making necessary cuts where sacrifices are warranted. This new era of Raptors basketball cannot be defined by the same mistakes left behind by Masai Ujiri.
I'm not expecting Webster will be perfect — heck, I can't even say he'll immediately reach Ujiri's level — but his ability to adapt and compromise will largely shape his tenure.