Masai Ujiri's biggest question isn't his own future, it's the future of the Raptors

·NBA reporter
·7 min read

Only the Toronto Raptors, with their painful history of retaining talent, could replicate the anxiety of player free agency but with an executive. 

Raptors president Masai Ujiri remains unsigned despite two years of speculation over his future. After the disaster in Tampa, the 50-year-old champion made a brief stop in Toronto to address the media, only to duck more questions about his contract, before capping his press conference by teasing Canadian Prime Minister Justin Trudeau to bring the Raptors home. A week later, Ujiri re-emerged in Kigali to take in the Basketball Africa League while rubbing elbows with Rwanda president Paul Kagame and French president Emmanuel Macron. By the looks of it, Ujiri may be closer to negotiating world peace than his own deal.

To be clear, Ujiri did not invite the fanfare even though he is more than worth it. Ujiri did what a great leader does, which is to take care of his team with general manager Bobby Webster and head coach Nick Nurse having secured lucrative extensions. His own status may be unknown, and even his wishes remain vague, but that's what you would expect from someone whose literal job is to negotiate. The famed executive who turned Andrea Bargnani into a lottery pick that was then conveyed in the Kawhi Leonard trade is now bargaining for himself with all the leverage, so you have to imagine the struggle that MLSE is in having to negotiate against the man they're paying to negotiate on their behalf. 

Odds still favor the Raptors despite the clock running out on Ujiri's contract. An MLSE source told Michael Grange of Sportsnet that they're "95 percent" confident that Ujiri will be retained, and even looking past the bravado, there is good reason for optimism. There isn't another opportunity in basketball that clearly trumps the Raptors' position. The noise around New York quieted substantially since their comeuppance this season, fringe hopes of expansion in Seattle is at least a few years away, and the biggest competitor likely remains Washington where the first order of business will be to shop Bradley Beal at the outset of a lengthy rebuilding project. So as long as MLSE meets the money, and shows the same ambition as Ujiri to continue growing the sport of basketball in Canada and globally, there is common ground to be found.

But the biggest question this summer isn't Ujiri's future, it's the future of the Raptors as whole. The granular decisions are on key free agents Kyle Lowry, Gary Trent Jr., and Khem Birch, and who the Raptors will select with their coveted lottery pick, but what's the bigger picture? What is the short and long-term direction of the team as it looks to navigate towards another championship? It was first to retain Kawhi Leonard who left, then the plan pivoted towards attracting Giannis Antetokounmpo who stayed, and now the Raptors are wrapping up a lost campaign where they finished 18 games under .500. There is confidence that retaining their current pieces, a return home and a clean bill of health will get the Raptors back into the playoff picture, but to borrow from Ujiri's own phrasing, playoffs for what?

The East is gaining strength. Brooklyn's superstar assembly should be favoured for the championship this season and beyond. Milwaukee locked in their core with Antetokounmpo, Khris Middleton, and Jrue Holiday. Philadelphia remains hugely formidable especially since Joel Embiid mastered the midrange, and now Atlanta is rising to the challenge led by Trae Young and a deep core that is entirely under 30. So even if the Raptors maintain, they will still be firmly in the second tier of the East, and that too will be competitive since Miami and Boston both feature two All-Stars level players in a down year. Things change quickly in basketball since this team game tilts so much on individual players, but who is that game-changer, how do the Raptors acquire him, and can they do so without compromising the rest of the roster?

It doesn't sound sexy but the most likely outcome is for the Raptors to build through the middle, meaning to remain competitive without bottoming out entirely for lottery picks, to collect talent as it becomes available (such as in the case of swapping out Norman Powell for Trent Jr.) and most importantly, to develop and improve the players on their current roster. Examples of building through the the middle include Milwaukee, Utah, Phoenix, and Denver, where none of them outright tanked for extended seasons, nor did they clean the books for superstar free agents to sign, and instead used shrewd drafting and advantageous trading to piece together their rosters. Better yet, the best recent example is the Raptors' championship team in 2019, which was assembled without any tanking or any blockbuster signings. Sure, it took a once-in-a-generation opportunity to buy low on Leonard, but the Raptors put in the work of developing, acquiring, and being courageous to pounce on the opportunity ahead of the rest of the league. The banner speaks for itself.

The key is to remain flexible, and the Raptors have all of their options open. There are no bad contracts on the Raptors' books, and even though this difficult season revealed more limitations for Pascal Siakam and Fred VanVleet than it did for their potential, both players would still be coveted pieces should the Raptors ever wish to move them. OG Anunoby made a leap in his game and even without any more changes, he would be a bargain on his current deal. Trent Jr. is restricted free agent, but so long as the Raptors keep him in the neighbourhood of $12 to $15 million, he is also a nice player with upside having averaged 15 points on 38 percent shooting from three as a 22-year-old. Add in Malachi Flynn's emergence in the second half of the season, a lottery pick next month, and holding all of their own selections moving forward, the Raptors have young talent with the ability to be competitive, to be developed, or to be moved if the right trade comes along.

Lowry is the one name that doesn't neatly fit this strategy. The 35-year-old guard is looking for a stable and competitive situation where he is paid accordingly for his continued excellence. The Raptors could meet all three stipulations on paper, but the one issue is flexibility. One of Lowry's stated wishes is that he wants to be somewhere where his teenage kids can be settled, and so the idea of re-signing Lowry only to move him a year or two into the deal isn't fair. Bringing back Lowry also means real sacrifices like VanVleet playing out of position as a smaller shooting guard (which he is capable and is willing), pushing Trent Jr. to the second unit where he is less successful, and sharply limiting Flynn's time. For those reasons, pursuing a sign-and-trade deal with Lowry would likely be the best outcome for the Raptors.

But other paths are also valid. A case could be made that the Raptors should retain Lowry and look to move some other pieces to sustain another playoff run. On the flip side, if next season also goes south, it would make sense to pivot towards the lottery at the trade deadline as the Raptors did this year. If the current core of Siakam, VanVleet and Anunoby show signs of levelling out, they may be pushed into trades that fit a longer or shorter term goal. If their lottery pick is a home run, it would make sense to shift the timeline younger. To build through the middle is to constantly revisit these scenarios. 

All of this will take vision to execute, and there are no guarantees in sports. The first question Ujiri needs to answer is if he will oversee the next phase for the Raptors, because there are no doubts about him or his staff. But once he does, the more difficult question will be on the future of the Raptors.

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