Raptors, Ujiri find themselves at crossroads ahead of trade deadline

TORONTO – When Masai Ujiri took the job atop the Raptors’ front office nearly a decade ago he came in with a plan.

His first couple moves of note were designed to clear the deck. He traded away Andrea Bargnani and Rudy Gay, a pair of high-priced veterans brought in by the previous regime, and Kyle Lowry was supposed to be next. The rebuild was on, until the unintended aftermath of those deals – and the Lowry trade that never was – forced Toronto’s newly minted general manager to pivot in a different direction.

At the time, the team was mired in a franchise record five-year playoff drought, and with the exception of the anomaly 2020-21 campaign in Tampa, it’s made the postseason every year since.

Now president and vice chairman, and one of the most well regarded executives in professional sports, Ujiri remains in the driver’s seat as the Raptors reach another crossroads.

The extent to which they’ve underachieved this season is up for debate. It’s not like they were ever meant to contend, as currently constructed. But coming off a promising year in which they made strides and ultimately finished with a 48-34 record, the expectation was that they would continue to show growth. Instead, they’re 25-30 and tied for 10th place in the Eastern Conference with one game left to play before Thursday’s NBA trade deadline, hence the dilemma.

Not only are Ujiri and GM Bobby Webster tasked with figuring out how to navigate the remainder of the season – do they push forward or take a strategic step back? – but they also have to determine where the franchise goes from here.

The former shouldn’t be causing them too much stress. It may end up resolving itself over time. Barring a late-season turnaround, they could always opt to rest their vets down the stretch in the event that they prioritize lottery balls over a spot in the play-in tournament. The ‘soft tank’ bared fruit once before.

But charting a path for the future? Those are the decisions that keep execs up at night. With that in mind, it’s impossible to overstate the importance of this week.

“Of course [it’s important],” said head coach Nick Nurse, whose team just returned home from an up and down but generally successful 4-3 West Coast road trip. “I think this is always a big week for the franchise, as is draft night, as [are] final cuts at training camp. Anytime there is a window, whether it’s large or small, to improve your team in any way, I think that is always important for the franchise.”

Ujiri and Webster were ever-present on the trip, but you’ve got to hand it to them, their poker faces are elite. We’re less than 48 hours from the deadline and rival execs are still wondering how the Raptors will approach it. Are they selling and, if so, to what degree? Will they be looking to add pieces that will help them now, next season or several years down the road? At least for now, it remains anybody’s guess.

That’s not to say they don’t have a plan. They likely have several of them. What’s made Ujiri successful in his role, perhaps above all else, is his ability and willingness to adapt on the fly, be flexible and call an audible when the situation calls for it. The mild-mannered, even-keeled Webster is the perfect complement.

They rarely box themselves into a corner. Even when they choose a path, it’s never definitive. They always leave themselves room to change course, if necessary. They’ve balanced the present and the future without one coming at the expense of the other.

At least to this point, they’ve resisted the urge to go all-in – Ujiri has never parted with multiple first-round picks in a trade – or, on the other end of the spectrum, completely hit the reset button. It’s why the people who want to see them to fully embrace one extreme or the other continue to be disappointed, and may be again this week.

No team has gotten more league-wide attention in the lead up to the deadline than the Raptors. Few players have heard their names come up in the rumour mill more than O.G. Anunoby, Fred VanVleet, Gary Trent Jr. and even Pascal Siakam. There’s always noise out there at this time of year, but given the circumstances around this club, it’s noisier than ever.

“I think it’s so noisy that it almost defeats the purpose,” Nurse said. “There’s so much noise it’s ridiculous and you can’t even pay attention to any of it… It’s so far-fetched that you don’t even have to react to it.”

“I’m at a point in my career where it really doesn’t matter unless I feel like there’s something going on,” said Siakam. “I’ve seen people go. I’ve seen people get here. So, nothing surprises me. I don’t look for anything until my phone actually rings.”

It’s not hard to get caught up in the sheer volume of reports. The rumours, the speculation, the mock trades – it’s a lot, and the Raptors have been at the centre of it for weeks. That’s what happens when you’ve underperformed and the top of your roster is made up of guys that other teams want. But if you’re anticipating the team moving on from three or four of its five best and most important players before 3 p.m. ET this Thursday, best to recalibrate your expectations. Taking their 10-year track record into account, that isn’t how this front office operates.

But even after a decade at the helm, in some ways, this is uncharted territory for Ujiri. For one, this is the most scrutiny he’s faced during his tenure. In a season like this, there’s plenty of blame to go around – players, coaches, management; they all share in it. Still, Ujiri has to take accountability for the failings of a roster that lacks shooting, rim protection and playmaking, among other things. With that comes the pressure to get them back on track.

These aren’t easy decisions that he has to make. What makes them even more difficult is how connected he is to the team and the individuals in play. It’s worth noting that the outbound players and people in almost all of his signature moves were guys he inherited with the job.

Bargnani and Gay were either drafted or acquired by his predecessor Bryan Colangelo. Terrence Ross and Jonas Valanciunas, who were each traded for key pieces of the 2019 championship team, were also Colangelo draft picks. While Ujiri considers trading DeMar DeRozan and firing Dwane Casey among the toughest things he’s ever done, they too predated him in Toronto.

Dealing Siakam, VanVleet or Anunoby would almost certainly hit different. All three are home grown – players that Ujiri and his front office drafted or signed straight out of college, developed and watch blossom into stars. How he feels about those guys is no secret; you can see the emotion on his face and hear it in his voice when he speaks of them. It sounds silly given the nature of the business, but he’s likened them to family.

There’s a reason why the asking price for those three is said to be substantial, bordering on unrealistic, and it’s not just because Ujiri is a shrewd negotiator. It’s because he values them more than most would.

This is a big week for the Raptors’ primary decision maker. It may also end up being one of his toughest yet.