Raptors Mailbag: Masai Ujiri's Future, Trade Options, and Schedule Talk for Toronto

The Toronto Raptors have one of the league's toughest schedules to start the year and there appear to be some big pivot points on the horizon for the organization

Jun 13, 2023; Toronto, Ontario, Canada; Toronto Raptors new head coach Darko Rajakovic, right, and team president Masai Ujiri pose for a photo after an introductory media conference at Scotiabank Arena. Mandatory Credit: Dan Hamilton-USA TODAY Sports / Dan Hamilton-USA TODAY Sports

We're a little over a month away from the start of training camp for the Toronto Raptors and there's not much going on these days. The roster is virtually set with one guaranteed contract up for grabs and I'm not expecting anything big to happen before the start of the season.

It seems we've moved past jersey talk, but there are still plenty of questions as we head into next season. As always, feel free to direct message me on Instagram or respond to my Instagram stories @aaronbenrose if you have a question for a mailbag article.

Why we always have the worst luck in draft lottery? - @the_avengerf4n

I wanted to address this one because it's not really true. Yes, losing the pick this year was unlucky if you choose to view it as such, but don't forget Toronto did move up to land Scottie Barnes. The Raptors were seventh on lottery night and had a 33.9% chance to land the No. 8 pick where Franz Wagner eventually went to the Orlando Magic.

Other than that, Toronto hasn't had many years in the lottery. It's only been since 2021 that lottery odds have been evened out and the Raptors did, of course, win the 2006 NBA Draft despite being sixth in lottery odds.

Should Jakob Poeltl be on this squad heading into this season or better to trade him away? - @yadhav7

He's going to be on the squad heading into the season at this point. If the goal is to compete to start the season while evaluating the core, keeping Poeltl around makes sense. That seems to be what the Raptors want to do entering the year.

That said, I see the argument for moving him. He's not part of the young core and his inability to space the floor restricts roster construction. Moving him would certainly thrust Toronto into the Cooper Flagg conversation too which wouldn't hurt. It just seems like the Raptors don't have an appetite for a full tank this season.

Isn't a tougher schedule great? High pick (coop) & our current 3 might not be enough for a title - @darshan_199999

I don't necessarily disagree. Toronto has a ridiculously tough start to the season and that might help to evaluate what this core looks like. If the Raptors look good against the league's best teams, maybe it shows us that Toronto is ready to take a step forward next year. Conversely, if the team struggles to start the year, the Raptors can pivot ahead of the trade deadline and make trades accordingly.

Getting that information early when Toronto and the competition are more likely to be at full strength is certainly going to be helpful. That said, if the goal is to compete next year, a bad start to the season could really derail the year.

In your opinion should the Raptors trade for Walker Kessler at the deadline? - @ali.beyoun24

Theoretically, the Raptors are either going to be buyers at the trade deadline because Jakob Poeltl has played well or they'll be sellers at the trade deadline in which case giving up future assets for Walker Kessler doesn't make a ton of sense.

Utah is going to be looking for future picks or young players in a deal for Kessler and I don't think the Raptors should be giving up either of those things in trades this season.

Is there a Masai departure in the near future? - @del101

Masai Ujiri's contract reportedly runs through the end of the 2026 season, according to Sportsnet's Michael Grange who has done some great reporting on the future of MLSE. Without getting too into the weeds, there's a sense that MLSE chairman Larry Tanenbaum plans to take a step back from the organization in 2026. Without Tanenbaum around, Ujiri's future with the organization may become more complicated. As the Toronto Star reported, Tanenbaum fought to keep Ujiri during his last contract negotiations with the organization.

We'll have to see how the next couple of seasons go and what Ujiri wants to do with his future, but there appears to be a potential pivot point on the horizon for him, MLSE, and the Raptors.

How would you compare the Raptors bench to the rest of the NBA? - @1m_jo3_k1ng

Toronto certainly has some interesting players on its bench this year, but it's a pretty young and undersized second unit without much firepower. If the Raptors bump Gradey Dick into the starting unit, the bench rotation probably looks like Kelly Olynyk, Davion Mitchell, Ja'Kobe Walter, and Bruce Brown. That's three guards who don't bring a ton offensively, at least not yet in Walter's case, and a veteran backup center who can't defend much at all.

Ochai Abgaji hasn't shown much offensive growth since joining the Raptors, Chris Boucher will likely start the year out of the rotation, and Toronto's second-round picks Jamal Shead and Jonathan Mogbo still need developmental opportunities.

Toronto has a lot of work to do before its depth is good enough to really compete among the Eastern Conference's best.