With Raptors at crossroads, Masai Ujiri faces his biggest test yet

TORONTO — On his lengthy resume as one of the most accomplished executives in recent NBA history, there is only one area where Masai Ujiri has a gap. An area of expertise not yet established.

The one thing that Ujiri hasn’t done, mainly because he hasn't needed to?

Build something from the ground up.

Well, he’s got his chance, thanks to a series of decisions of his own making that came with some unintended consequences.

There’s no reason to think he can’t pull it off, but if Ujiri can’t there will be nowhere to hide.

This isn’t a case where he’s inheriting someone else’s problems and rolling up his sleeves to clear out their incompetence. Ujiri is in year 10 with the Raptors. The myriad successes are his, and the stumbles are too.

The trend of late is not positive. Two years ago the Raptors won 48 games, last season they won 41 and this season they are on pace to win 32 after they dropped a 116-110 decision to the visiting Chicago Bulls at Scotiabank Arena that saw Toronto fall to 16-26 on the season and the Bulls improve to 20-23. The Raptors went up by four with 4:15 when newcomer Bruce Brown (15 points on 7-of-10 shooting) scored a layup. But the Bulls closed with a 13-3 surge that included a late bucket and pair of free throws by former Raptor DeMar DeRozan.

DeRozan being in the building — not to mention Raptors legend Vince Carter, who was broadcasting the game for TNT — underlined how quickly and dramatically teams can change, and not always for the better.

A year ago the Raptors had a former all-star at point guard (Fred VanVleet), a two-time all-NBA player at one forward (Pascal Siakam), an all-NBA defender at the other (OG Anunoby) and the reigning rookie of the year doing a little bit of everything (Scottie Barnes).

Now? Only Barnes remains and for all his promise, it’s a lot to put the future of a franchise at the feet of a 22-year-old, even one capable of going off for 31 points, seven rebounds and six assists as Barnes did against Chicago, but the Raptors are doing it. They have no choice, honestly.

“I don’t know if he is ready for that responsibility, but we have to put him in position,” said Ujiri. “That’s our job. We have to put him in position to at least grow and start to see dividends of the work he is putting in… the hardest thing to do in this NBA is to find those kind of players… that has that basketball IQ, that has that size, that develops his shooting, has the charisma, has the character to become that player.”

The Raptors hoped that Siakam would become that kind of player and to be fair, the 29-year-old from Cameroon came pretty darn close. But the Raptors decided he couldn’t take them to where they wanted to go and didn’t want to pay him the contract he was asking for unless he could. For all the thoughts expressed on the issue, the reason the Raptors split with one of their franchise icons is as simple and complicated as that.

Did the Raptors have options? Did they wait too long? Did the trade saga that enveloped the franchise for the better part of a year need to be as long and drawn out, especially if at the end of it the return was fairly underwhelming?

To his credit, Ujiri allowed that his team is headed for some uncharted territory in his lengthy, wide-ranging press conference where he laid out some of the thinking behind the recent trades of franchise stalwarts Anunoby and — on Wednesday — Siakam, the last remaining core pieces of the championship legacy Ujiri shepherded into existence.

The next steps could take longer, and the path to success is by definition more uncertain.

“I don’t know if to call this a rebuild or a reset or however we want to put it,” Ujiri said. “But a normal rebuild with other teams takes five [or] six years. Do we have the patience for that? You know? Like do we have the patience for three-to-five years building of our team? Some way, somehow we are going to have to have patience.”

Ideally trading a player of Siakam’s calibre would provide a considerable kickstart in that process, but in this case, not really.

The Raptors walk away with two picks in the latter half of the 2024 draft which is projected to be historically weak. "Awful," was how one Eastern Conference general manager described it. Even Ujiri wasn’t trying to sugar-coat it. He may end up with three first-round picks this summer but acknowledges he’s likely not going to use them.

“I believe in our [front office] team and what we do, and I think we’re going to make best use of it,” said Ujiri. “Are we going to take three picks in that draft? I strongly doubt it. That’s not the plan for now, but I think we’ll make good use and scout it the best possible way we can.”

The 2026 pick they got from the Pacers could be more useful, but most likely projects to be in the middle of the first round at best. The player they’ll be taking is in Grade 11 right now, so likely of no help any time soon.

Missing is the kind of tentpole young talent that everyone can point to and say, 'see it was worth it!'

Certainly Brown — who was mostly included for salary-matching purposes — has a lot of fans around the league. One Western Conference source suggested the versatile wing could yield a protected first-round pick from a team eager to round out their depth for a playoff run.

And for all that’s happened in the past few weeks, Ujiri was clear: With three weeks to the trade deadline, he’s not done.

“Definitely,” he said when asked if he expected to be making more trades. “You look at this and that's why we have created flexibility and next three weeks is, there are all of these windows, whether it's now, whether it's the draft, whether it's free agency, that's why we've created flexibility to make this team grow and continue to be bigger and better and exciting for our fans because I think there's upside here.”

But if the question is could the Raptors have done better had they started their rebuild last season at this time or in the summer? The consensus elsewhere seems to be yes, they could have.

“They should have done this last year,” said one league executive. “They kept it together to be what, a 45-win team at best?”

Not even, turns out.

Ujiri says that when he compares what he could have had in trade in the summer or last year at the trade deadline “it balances out.” But it seems hard to imagine that somewhere along the way there wasn’t a chance to add a high-end young talent when dealing a two-time all-NBA player in his prime. We may never know.

But what’s done is done, at this stage. The question is what is coming next. Ujiri’s done a lot of things in his career, but rebuilding a bad team isn’t one of them. The team he took over in Denver in 2010-11 was coming off a 53-win season. Ujiri had to cut his teeth by trading then Denver Nuggets star Carmelo Anthony in his first season on the job, but ended up pulling off a deal that was widely praised. Three years later his last team in Denver won 57 games.

When Ujiri joined the Raptors in 2013-14 he thought he was going to be rebuilding. He famously had a trade worked out to send Kyle Lowry to the Knicks in November of 2013 but the Knicks reneged. It’s arguably the best thing that ever happened to Ujiri and the Raptors. Lowry spearheaded the longest run of success the Raptors have ever had and may ever have: seven straight playoff appearances, a trip to the Conference Finals in 2015-16, a 59-win season in 2017-18, the championship in 2018-19 and the NBA’s second-best record in 2019-20.

But the returns since have been less-than-encouraging. The centrepiece of the Lowry trade was Precious Achiuwa, an experiment that ran its course in Toronto and is getting even less traction now that Achiuwa is in New York. VanVleet left as a free agent for no return. The Anunoby trade looks like a solid bit of business, yielding Immanuel Quickley and RJ Barrett, but there have been misses in the trade market and at the draft table. How much different would things be in Toronto if the Raptors had drafted budding all-star guard Desmond Bane with the 29th pick in 2020, rather than since departed Malachi Flynn?

No executive bats 1.000, but Ujiri’s success rate has taken a bit of a hit lately and even the personal touch with which he conducts his business seemed to go missing throughout the past year with Siakam. Ujiri went so far as to acknowledge that keeping Siakam at arm’s length throughout most of the process rather than potentially working collaboratively when it was clear that coming to an agreement on a new contract was going to be problematic was a regret now that the deal is finally done.

Siakam wanted to remain a Raptor — albeit not necessarily at the price point Toronto had in mind — and was described by those who know him as heartbroken at the fact that the Raptors didn’t seem to value him even after emerging as one of the franchise’s ultimate success stories: From the 27th pick in the 2016 draft to all-NBA in the space of four seasons.

“I think the lines of communication in the summer were not that great. Like, just because sometimes I don't have answers,” said Ujiri. “ …but based on my relationship, you know, like Pascal deserves [better] …even [to have] over communication, which I didn't, and I apologized to him for it. I apologized to him before the season started and I apologized to him again recently. Yeah, that part I'm not particularly proud of…”

Ujiri has plenty to be proud of in his decade running the Raptors. On the whole it’s hard to imagine an executive having a better run with the franchise. But after some lean years the team he’s run so well is at a crossroads, and it’s up to Ujiri to pick the right direction and light the path accordingly.

For all the success he’s had, it may be his biggest test yet.