Masai Ujiri leads the Raptors’ delicate dance: Can they be good without being too good?

Welcome to the 30th Raptors season, in which team president Masai Ujiri will attempt to do a delicate dance around a potentially vicious circle.
In one moment during Monday’s media day, Ujiri talked about the coming 82 games as a rebuilding project. And in the face of a potentially league-changing draft class in 2025, led by Duke uber-freshman Cooper Flagg, putting in another losing season, after last year’s 57-loss campaign, might well be in the franchise’s best interest.
Not that it’s simple. In the next breath, Ujiri stressed how important it is that his current core continue learning how to win under second-year coach Darko Rajakovic. Which also makes sense, since the list of the NBA’s obviously tanking teams is already long, and the Raptors, led by 23-year-old all-star Scottie Barnes, might be a little too good to truly compete in the NBA’s race to the bottom.
“I don’t want (the players) to talk about rebuilding. That’s me,” Ujiri said. “They do their jobs, we do our jobs.”
Indeed, there are real dangers to developing high-priced players in an organization bent on losing. And with an ownership change afoot at Maple Leaf Sports & Entertainment, Ujiri, now more than five years removed from the championship halo, could use a public reminder that he actually knows what he’s doing.
So as much as there’s a case to be made for floundering for Flagg, there’s an internal argument to be made for pushing for every win, even if that might mean the Raptors top out as a play-in tournament participant, and even if that might not be the best outcome for the organization’s long-term future.
“We’re going to play to win, but it is a rebuilding team,” Ujiri said. “I think everybody sees that loud and clear.”
If everybody sees it, anyone with a brain also sees the inherent contradictions. And if everybody sees it, you don’t get the sense everybody is particularly excited about it. Vince Carter’s divisive jersey retirement Nov. 2 figures to be Exhibit A in a 30th-anniversary season of nostalgia, revisionist or otherwise, that will be there to provide a potential distraction if the on-court product underwhelms. Which is more than possible.
This is a sophisticated basketball market with relatively recent experience in watching the assemblage of a championship roster. And as much as it’s fun to dream, it’s still a reach to see a team built around Barnes, Immanuel Quickley and R.J. Barrett as heirs to title-winning royalty like Kawhi Leonard, Kyle Lowry and Pascal Siakam.
“We have a clear path now going forward,” Ujiri hazarded on Monday.
From a lot of angles, the path is as clear as mud. And the questions are many. Can Barnes, fresh off signing a max contract, make the competitive jump toward being the kind of NBA alpha you can build around? There’s optimistic talk within the franchise that Barnes spent the summer showing he’s matured into a serious pro who’s more focused than ever on fully unlocking his obvious potential. If he does, Barnes, more than anyone, can single-handedly raise the organizational ceiling.
Can Quickley, he of the five-year contract extension worth $175 million (U.S.), justify his new money while establishing himself as Barnes’ chief complement (and raising last year’s dismal 45 per cent make rate on two-point field goals)? Can Barrett shed his reputation as a defensive liability while diversifying an offensive arsenal that’s sometimes too heavy on tunnel-vision beelines into coverage? And can the slumping Raptors’ developmental department turn one of its young players – 2024 first-round pick Ja’Kobe Walter tops the list – into a starter-level asset?
If that answer to most of those questions is yes, maybe the path is as clear as Ujiri claims. Maybe Barnes, Quickley and Barrett — rounded out by an improving Gradey Dick, veteran glue guy Jakob Poeltl, and some younger pieces — can be the makings of a winning program.
And if the answers shade toward no or the injuries pile up – well, a late-season shift into reverse, a la the 2021 Tampa tank that produced the No. 4 draft pick that procured Barnes, would arguably be this season’s best-possible outcome. The Raptors need more talent in their midst, full stop. On this, there’s no argument.
That’s what makes the task of simultaneously rebuilding and winning so difficult. That’s why Ujiri has a lot of work to do to get fans believing in the upside of this team more strongly than they believe in the merits of an uptick in Toronto’s draft-lottery odds.
For all that, the situation is further complicated by the shifting sands of MLSE ownership. With the wheels in motion for Edward Rogers to become the czar of Toronto’s pro sports scene, it’s easy enough to portray Ujiri and Rogers as boardroom enemies, given Rogers’ public attempt to kibosh Ujiri’s pricey 2021 contract extension.
Ujiri did his best to smooth over that rough patch Monday, insisting the episode was the ho-hum stuff of a tough contract negotiation, and that all’s been copacetic since. Still, Edward Rogers is a cutthroat businessman who is about to hold unprecedented sway over the Raptors and everything else under the MLSE umbrella. Anytime there’s a new boss in town is a good time to be winning.
“I know I’m going to be judged on the way I do this job. That’s the way we’re going to be judged – on what happens on the basketball court,” Ujiri acknowledged.
That’s probably true, unless what happens on the basketball court somehow shows the inherent potential of Ujiri’s current squad while also landing the Raptors a top pick in a tantalizing 2025 draft. It’ll be a difficult needle to thread, to be sure. But as Edward Rogers would be the first to point out, Ujiri is making an awful lot of money. If anyone can make a delicate dance look doable, it ought to be him.