Raptors mailbag: Masai Ujiri’s replacement? Are they a playoff team?

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The NBA draft is over, free agency is underway and Summer League tips in less than a week as the page turns to the 2025-26 season.

Which means it’s a good time for a Raptors and NBA mailbag. Wasn’t surprised to see a lot of questions about the departure of Masai Ujiri and his possible successor.

Thanks as always for the queries. Here’s Part 1:

Pierro @Oliaros2: “Are we, for the foreseeable future, going to be Washington Wizards bad? Or are we going to be in hateful NBA purgatory: too good to get a high lotto pick that pushes the team forward, not good enough to contend for the playoffs.”

RW: It’s amusing to ponder this in the wake of Masai’s exit since he was adamant the middle was no place to be in the NBA (an accurate statement). He was always dead-set against the Raptors lurking there. I believe in the near term the team will indeed be too good to get a high lottery pick (assuming the key players stay healthy), but I’m more optimistic about the playoffs. In the West they’d be near the bottom, but the East stinks, so the play-in is my absolute floor for these Raptors. Only Cleveland, Atlanta, Orlando and New York seem definitively better. That leaves four playoff spots for Boston (no Jayson Tatum, Jrue Holiday or Kristaps Porzingis), Indiana (no Tyrese Haliburton or Myles Turner), Detroit (weakened by some defections and no longer benefitting from the element of surprise), Philadelphia (if two of Joel Embiid, Paul George or Jared McCain play 60 games apiece, which is far from guaranteed), Milwaukee, and maybe Miami for Toronto to fight it out with.

Brooklyn, Charlotte, Washington, Chicago, Miami, weakened Indiana and Detroit seem less talented than these Raptors, but we’ll see.

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Sean @Whispering375: “Who in your opinion would be the front runner on Masai’s job? And if they do hire someone outside of Bobby, don’t you think that new person would want a new coach and management?”

RW: Ujiri built a very diverse front office complete with a little bit of everything ranging from a jack of all trades with a specialty in the salary cap in Bobby Webster, lots of people with scouting backgrounds, someone who was in media relations (and scouting) in Dan Tolzman, analytics (Keith Boyarsky), and even a former journalist (Luke Winn), amongst others. One thing they don’t have is a former agent in a prominent position. That’s been the trendy thing in the NBA for a while now (like with Leon Rose in New York). To that end, Bob Myers would be a great candidate, but can’t imagine Rogers would meet his price or he’d want to move his family at this point, but you never know. Ideally they’d find an agent-type to work under Webster and maybe even Tolzman, but not sure how likely that is. As you mentioned, it’s tough to hire someone above as they usually do want their own people (and I think Webster and Tolzman are more than deserving of showing what they can do in the top two roles. Both are extremely well-regarded league-wide and it would be a shame if Rogers turfed them solely as further cleaning out of the old Ujiri regime.

I’m not the only one that’s thought a former (or current) agent is most likely to come aboard, but don’t know specific candidates.

Another idea is a veteran presence in the mix, which was lost when Jeff Weltman went to Orlando years ago. Someone with decades of experience in management as the great Wayne Embry is not a daily presence with the franchise.

Or, an out of the box one, what about Steve Nash? (Though that would mean you could shut down all those RJ Barrett trade rumours, since Nash is his godfather).

Freeman Igers @freemanigers: “Do you think Masai’s departure is more performance related or compensation?”

RW: A little from Column A, a little from Column B, but they’re related. From what I’ve been able to report from sources, Ujiri wasn’t keen on Raptors life post-Larry Tanenbaum with Edward Rogers calling all the shots and Rogers wasn’t willing to pay Ujiri anything close to what he wanted anyway. So there was no pathway to Ujiri sticking around. If Tanenbaum wasn’t on the way out (reports have said Rogers can buy his shares by next summer, they just closed their purchase of Bell’s shares this week), there was a good chance Ujiri would stick around a bit longer. But the team’s struggles over the last half-decade really soured Rogers on Ujiri at his upper echelons of NBA executives compensation point.

Just Win @gsess.bsky.social: “How much of the current Raptors makeup was Masai and how much is Bobby (who has been GM for years now)? Do you expect significant changes on the court to reflect those differences (what major differences in philosophy might Bobby have)?”

RW: Bobby has a different background than Masai, who was always a scout through and through. Webster came up studying and anticipating league trends, helped write a previous CBA, saw how the Magic operated back in the day, etc. It’s too early to know how different he will be making the final call. He and Ujiri and Tolzman were aligned on a lot of the prospects they previously liked and the room has always been very inclusive, with opinions solicited from everyone. “Cross-checking” was a key principle and everyone was encouraged to give their opinions on prospects or trade targets and I wouldn’t expect that to change.

@WolstatSun