Sometimes, you can just see something coming from a mile away. Despite one's best efforts to keep things secret, there are always eager beavers who can decipher it right from the start. Movies, sports, even within your own circle of friends and family; this sentiment seems to resonate across a wide range of situations. Heck, sometimes even the folks who are supposed to be keeping everyone on their toes just aren’t the best at keeping things under wraps.
I believe many people — not just within Raptors Nation but across the wider basketball community of pundits and analysts — were already seeing the open vacancy at the top of the Raptors' basketball operations as a perfect fit, seemingly waiting for Bobby Webster to step into the role.
And they had every reason to think so, given that Webster had largely been Masai Ujiri's right-hand man throughout his tenure and gradually began to take on more prominence in press scrums, conferences, and other media appearances, representing the Raptors organization.
In the latest from NBA insider Jake Fischer, he sheds more light on the Raptors' strategy leading up to the Webster promotion, revealing that some in the NBA world were taken aback by Toronto’s approach. The team’s creation of ambiguity around their open job vacancy process could've been done to surprise the rest of the league.
Raptors tried to keep rest of NBA on edge prior to Bobby Webster news
Here's an excerpt from Fischer's Bleacher Report livestream on YouTube from August 20:
"And this is kind of what the league was anticipating [referring to Bobby Webster's promotion]. In fact, when the Raptors put out a formal statement about parting ways with Masai Ujiri, there was written language in that statement that the Raptors were now "beginning a search for their new head of basketball operations."And there was someone I consult with who is involved in, you know, search firm stuff about executives and whatnot, who was taken aback by the fact that was even put out publicly. He just kind of was taking it and the league was taking it as just a foregone conclusion that Bobby Webster was going to be running the show here. "Jake Fischer, Aug 20, 2025
I have no doubt that Webster was at the top of the Raptors organization’s list, but I also believe the franchise likely explored other options before settling on Bobby Webster. Last month, I mentioned that rumors suggested the Raptors were in discussions with names like Dwane Casey, Pacers president Kevin Pritchard, Bob Myers, and even some older whispers linking Giannis Antetokounmpo's agent, Alex Saratsis, to the process.
Like I mentioned in the caption of this piece, who doesn’t enjoy a touch of suspense and intrigue en route to an announcement everyone knew was coming? It's likely the Raptors, viewing things from a business perspective and considering their position within the broader NBA landscape, preferred to keep the league guessing rather than simply confirming, “Yeah, Bobby Webster is our guy,” right from the start.
And in the end, Webster still got the position, so it all worked out. Though, some Raptors fans remain a bit suspicious of the MLSE ownership and how they managed the whole situation.