Masai Ujiri's future with Raptors front and center after trade deadline

The Toronto Raptors finally snapped their nine-game losing streak on Wednesday at home against the Denver Nuggets. Kyle Lowry was a career-high plus-42 in the win, gesturing at the camera after the game as he walked to the locker room and then holding a 22-minute session with the media. It felt like a farewell to the greatest Raptor of all-time. And then the trade deadline passed the next day, and he stayed.

Toronto did take a step towards building for the future by trading Norman Powell to Portland and recouping some draft capital in separate trades that sent Matt Thomas to Utah and Terence Davis to Sacramento. But the decision not to trade Lowry as he heads into free agency this summer left a lot of fans scratching their heads.

The post-trade deadline Raptors lost two more games to wrap up the week against Phoenix on Friday and last night to Powell and the Trail Blazers. They haven’t addressed their glaring hole at center or improved the team’s depth, and with 26 games left in the season, this team is getting increasingly close to just playing for a draft lottery position.

Here are three questions about the Raptors heading into the offseason after a somewhat confusing trade deadline:

Will Masai Ujiri be leading the Raptors into their most important offseason in years?

Masai Ujiri was asked directly to address his uncertain future with the team when he met the media after Thursday’s trade deadline. He laughed and gave a non-answer, essentially punting the question to the summer, when his contract will be up. If anyone is trying to parse every word Ujiri said in his presser, then a pessimist would point to the fact the Raptors president reassured everyone that the franchise would be in good shape with or without him.

Has he made up his mind on leaving for another opportunity after this season? Is Ujiri going to make a decision when the season is over? Will he even work for an NBA team next season or pursue goals outside of the sport? The questions surrounding Ujiri’s future have lingered since Toronto won a championship two years ago and no long-term extension was agreed upon with MLSE.

We’ll finally get an answer this summer. As Ujiri’s contract is up, and you would imagine before the team heads into the offseason, they’ll first need to address whether Bobby Webster will take over running the front office or if their president is returning.

The patience, or stubbornness, of the Raptors’ refusal to trade Lowry at the deadline was very much in line with how Ujiri has operated with the team. We’ll find out in a few months whether he’ll still be here to help the franchise transition into a new era.

Did the Raptors miss an opportunity to get a return for Kyle Lowry?

Two schools of thought have emerged from Toronto’s refusal to simply take the best offer on the table at the trade deadline for their franchise cornerstone. On the one hand, teams are bewildered at the Raptors’ asking price for a 35-year-old point guard who would either be a short-term rental or an aging player commanding a salary in the range of $25 million annually this summer. On the flip side, plenty of Raptors fans believe there was no offer appealing enough for Lowry, who would have raised the ceiling for any team he joined.

Another team with a different relationship with their point guard would have simply taken the best offer at 3 p.m. on Thursday. Still, the Raptors weren’t enamored with Philadelphia’s refusal to include the draft compensation and young talent they were looking for, or the Heat’s package without Tyler Herro and the Lakers’ last-ditch attempt at trading for Lowry while holding on to Talen-Horton Tucker. The Raptors have a close working relationship with Lowry, and the two sides can likely come together on a sign-and-trade if he wants to land somewhere else this summer. If that’s the case, Toronto could get a similar package to what they were offered at the deadline.

The disastrous scenario would be watching Lowry leave this summer and sign with another team without getting anything in return. The team would have watched Kawhi Leonard, Danny Green, Serge Ibaka, Marc Gasol and Lowry leave over the course of three summers without replenishing their roster with assets in return.

Of course, there’s also a third scenario. Lowry surveys the offseason landscape, and no team can provide both the winning environment and annual salary he’s looking for, and he agrees to return to the Raptors once more. We’ll find out this offseason whether the Raptors made a mistake at the trade deadline.

Which direction will the team want to go next season?

Here’s the most likely path for the Raptors this summer. They figure out Ujiri and Lowry’s future, replenish the roster through the draft, re-sign restricted free agent Gary Trent Jr. to a contract that will be less expensive than what they were expecting Powell to get, and use their remaining cap room to fill out the roster, specifically at the center position but also for a bench that requires a complete makeover. With or without Lowry, this path would get the Raptors back to a team that would likely win around 45-48 games next season and be right back in contention for a top-four seed in the East.

But there is another path the Raptors could take. They can look at the roster and decide if they want to build around Fred VanVleet, OG Anunoby and Pascal Siakam. That is the current core of the team moving forward. Could we see Siakam be made available in trade talks? Would the team consider taking several more steps back to assemble the best team in, say, five years? Right now, a full teardown of the roster seems unlikely this summer, but it is a decision the Raptors have to make. For everyone who has advocated for the team to tank and lose games the rest of the way for a higher lottery pick, this is the route you would be pushing for because one draft pick isn’t going to change this team’s trajectory next year.

Either way, many important decisions are coming this summer, and one thing is for sure: the roster and perhaps even the front office will look a lot different when the 2021-22 season starts.

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