Masai Ujiri's rebuilding Raptors are at an inflection point

The Toronto Raptors were still dripping with champagne on the night of June 13, 2019, when ESPN published a report that the Washington Wizards were preparing a "staggering financial package" to try to lure Raptors president Masai Ujiri to the U.S. capital.

Aside from the awful optics of leaking an interest in a team's top executive at the very moment it was celebrating its first NBA title, the story was a cold bucket of water to the collective face of Raptors fans.

Ujiri had as golden a reputation as it was possible to have. He'd taken over a franchise best known as a place good players left at the first chance and built contending teams that won a title when he placed a high-risk bet on a disgruntled superstar.

Of course other teams would look to poach him. The only question was whether Toronto was big enough to keep Ujiri around. The Wizards' interest never materialized, possibly because they blew their chance with their ill-timed leak, but months later it was the New York Knicks who were said to be sniffing around. If few teams could offer a better market than Toronto, New York was definitely one of them.

Eventually, that passed, too. The Knicks hired player agent Leon Rose to run the team and Ujiri re-upped with the Raptors in 2021, with vice-chairman added to his title.

It seemed like a coup at the time. The Raptors held on to one of the NBA's most highly regarded executives, and the only one to build a consistent winner in the franchise's quarter-century of existence.

Whew.

But with the Raptors underway at training camp before a new season, it's hard to escape the sense that this could be an inflection point for Toronto and the most successful franchise steward the city has seen since Pat Gillick. Ownership changes at Maple Leaf Sports and Entertainment, the Raptors' corporate parent, will see Rogers Communications assume majority control when its purchase of Bell Media's stake eventually closes.

Ujiri recently said he has a fine working relationship with Rogers boss Ed Rogers, but it's been widely reported that the telecom executive was reluctant to sign off on the giant compensation package that was part of Ujiri's contract extension. With Rogers soon to be firmly in control, and minority owner and Ujiri ally Larry Tanenbaum somewhat marginalized, the Raptors front office is a more precarious place to work now than it was a month ago.

Perhaps more importantly than all that is the direction of the franchise. Ujiri's impeccable work in building the title-winner was followed by a robust championship defense even after Kawhi Leonard left, right up until the COVID pandemic blew everything up.

It's impossible to know what would have happened had the Raptors not ended up marooned in Tampa the following season, but there's no denying that the transition to a post-Kawhi, post-Kyle Lowry era didn't go as expected. Ujiri waited too long to rebuild and ending up having to jettison Pascal Siakam and OG Anunoby for trade packages that would have been better a year earlier. He also lost Fred VanVleet to free agency for nothing.

Mostly the Raptors succeeded in giving those three players, who were supposed to be cornerstones of the next contending Toronto team, the platform to sign new megadeals elsewhere.

And so now Ujiri has his next-gen Raptors, built around Scottie Barnes and Immanuel Quickley. Give him a couple of seasons, and it's possible to imagine the Raptors boss building another strong team, only because he's already proven he can do it against difficult odds. There was a time, after all, when it seemed likely that LeBron James would humiliate the Raptors every spring until the end of time. Then, all of a sudden, they were raising a championship banner.

But even an optimist has to think that days of possible contention are some way in the distance now. There are nine teams in the East - last year's playoff teams, plus Atlanta - expected to win significantly more games this season than the Raptors, who if they manage 30 victories will outperform their Vegas over/under total. This is the first season since Ujiri arrived in 2013 that his team is expected to be noncompetitive from the outset.

And it could easily be worse than that. The roster is long on youth and short on depth, and poor injury luck among any of the projected starters would be disastrous. Even if they stay healthy, the Raptors are likely to be on the wrong end of a lot of blowouts, and will have regular visits from Siakam and the Pacers, Anunoby and the Knicks, and Lowry (and Nick Nurse) with the Sixers to remind them how far they are from a playoff team. At least VanVleet and the Rockets will only come to town once.

How many wins do the Raptors need for Ujiri to keep his job? It's a question that can at least be asked. Not that long ago, it would have been unthinkable.

Scott Stinson is a contributing writer for theScore.