How worried should we be about Masai Ujiri leaving the Toronto Raptors?

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As a nervous people, we Raptors fans are never quite at peace with the state of the team. Part of this, of course, is natural to the concept of competition, the idea of never being satisfied, of always striving for the next thing, then the next, and so on. It’s how Raptors fans can find themselves coming off the greatest two-year run in franchise history — which included a championship victory and spirited defense — and still be a bit on edge. But as the adage goes: is it worse to be paranoid or to know you should be?

This brings us to today’s concern in Toronto. Last week, team president Masai Ujiri gave his annual end-of-season address, which continues to work as a review of the past season and a quasi-State of the Union speech for the Raptors. Owing to the extremely strange nature of the NBA’s 2019-20 year, Ujiri had to hold this press conference in mid-September — whereas he’d usually hold it in May or June before disappearing for summer vacation. (Or Summer League, but you get my point.) He also had to field questions about his contract situation, which, for the first time in a long time has been left unresolved.

Some quick history: Ujiri was signed to a five-year deal as the Raptors’ team president and general manager in the summer of 2013. He helped remake the team over the next couple of seasons, leading up to the consummation of a multi-year contract extension in 2016 after the Raptors made their first-ever appearance in the Eastern Conference Finals. It was clear in the summer of 2016 that MLSE and their spokesman Larry Tanenbaum were going to do what was needed to keep Ujiri happy. That extension, however, is on its way to running its course, with one more year on the books and Ujiri unsigned beyond the 2020-21 season. There has yet to be an official update from MLSE on the matter. Cue the panic in Toronto.

If we could zoom out for a moment, however, there are reasons to be optimistic for Ujiri’s return. First, is perhaps the most obvious: heading into this off-season for the Raptors, the team had to address the status of their head coach, Nick Nurse, and their GM, Bobby Webster. (Ujiri abdicated that title after his contract extension went through and previous GM Jeff Weltman departed for the Magic.) On the Nurse front, Toronto acted quickly, re-signing their reigning Coach of the Year to a hefty $8 million per year contract — making him the fourth highest paid coach in the league. This swift decision struck the appropriate note of seriousness from the Raptors.

But wait, that’s not all. Up second, as confirmed by Ujiri’s address, a deal with wunderkind Webster is apparently also in the works. “We’re close,” was how Masai defined the situation last week, suggesting his protege in the front office is close to returning as Toronto’s GM for the future. As far as dominoes go, for the Raptors to jump on the Nurse re-signing and then reveal they’re already hard at work trying to keep Webster in the fold suggests the next move will be to confirm the return of the biggest domino of all: Ujiri.

Now, the third positive here, which is admittedly harder to pin down, relates to where else Ujiri could possibly go. Usually when discussing free agent players, there’s always a regard given to the market forces at work. Toronto’s Fred VanVleet, for example, could command a high salary if there are enough teams in the market for a starting point guard. If there aren’t, well then his value may drop a bit, or he may find only the Raptors calling him to re-sign. A similar logic applies to Ujiri. We know the demand for Ujiri’s services is quite high — and it likely always will be given his track record — but are there any current positions open? With the front offices of perenially interested teams like the Knicks and Wizards now full, the answer may very well be: no. Though by next summer, perhaps that could change.

Which is how Raptors fans come to feel a bit nervous. When Ujiri was installed in his front office role, his stated goal was to win an NBA championship. He spent the next six seasons attempting to do just that — and then, he actually succeeded. When you consider the history of the NBA and how difficult it is to win a title — before even considering the specific history of the Raptors — this is an astounding achievement. And while credit goes to the players and coaches for actually playing the games, Ujiri has earned his due as the mastermind of the whole scene, the man who put all the gears in motion over all those long years to produce that ultimate golden moment in the summer of 2019. Given his starting point, it’s almost like Ujiri willed it into existence.

But like Alexander the Great before him, there may not be any more lands for Ujiri to conquer in Toronto. Is it possible he may move on in search of some greater challenge in the NBA, some new impossible dream to fulfil in time? Could he desire to move beyond basketball’s day-to-day grind to build his organization Giants of Africa and/or the basketball scene of that continent with an even greater and more intent focus? Is there a grander league office position within reach, or even some political post that could use a savvy mind like Ujiri’s? These are all just wild guesses at this point, but it’s fair question to ask. Just how high has Masai set his sights?

In that sentiment, perhaps we can find some comfort. While the timing may not be right for MLSE and Ujiri to work out an agreement, it’s clear that whatever Masai asks for will be earnestly entertained in negotiations. Maybe he’s holding out for more money or he wants an ownership stake in the Raptors. While no one man is more powerful than the combined corporate might of MLSE, no one man has been better at building the Raptors into the big-time brand it has become. Ujiri has made a semi-defunct basketball organization into a league powerhouse. This gives him tremendous leverage. And since we know how patient Masai can be in his standard NBA dealings with players and agents, we can understand why he would take his time here. Ujiri knows who he is and what he has.

With the summer of 2021 looming as the biggest free agent bonanza of the past decade, MLSE likely sees the role Ujiri still has to play for Toronto. While we ourselves have been willing the idea of “Giannis to the Raptors” into existence, it’s Masai who could be the key figure to actually make it happen. He’s already been planning for years with an eye towards that exact moment, after all. And while that’s just one possible outcome, MLSE must know this too.

So, sure, everything has a price. And, sure, maybe Webster or someone else could do Masai’s job with the Raptors just as well. But there are some things that bring a value beyond the dollar figure at the bottom of a contract. Ujiri’s presence in Toronto counts as one of those things. Now let’s see if both sides can agree on that.