OverDrive - Lewenberg on the Raptors parting ways with Ujiri, the acclaim for the organization and next steps for the franchise

Episode Date: June 27, 2025

TSN Raptors Reporter Josh Lewenberg joined OverDrive to discuss the Raptors parting ways with Masai Ujiri, his noteworthy acclaim for the organization, the ripple effects for Bobby Webster's managerial role, his interest from around the league, the next steps for the Raptors and more.

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were you surprised by this, the timing of Masai Ujiri partying, mutually parting of the ways with the Raptorsors and considering that it's after the draft, but right before free agency officially begins? Yeah, no, that's just it. Nail on the head there because like the surprise here is not that it happened. I think a lot of people sort of saw the writing on the wall, both in terms of Masai's contractual situation when you're left on his deal going into this season as a lame duck executive. But then also the changes at MLSC both in terms of ownership and philosophy.

And then with the Shanahan news coming down recently as well. So like, this always seemed like a distinct possibility, if not an inevitability. But yeah, the surprise is the timing a day after the draft just before free agency. And I mean, I saw Mathai a couple days ago. It sounds like this has been in the works for at least a little bit. He probably would have known that the axe was coming pretty soon. And I got to say, like, good poker face on Masai because he seemed pretty jovial. He seemed like himself. I certainly didn't get the sense that this was imminent, but here we are.

I woke up today expecting to meet Colin Murray Boyles and instead I eulogize the iconic tenure of one of the most impactful figures in the history of Canadian sport. Yeah, that's a great way to put it, Josh. Let's not forget that as we bid adieu to Masai Ujiri. We had Danny Green on a little earlier, Josh, and he was talking about how, as a member of that 2019 Raptors groundbreaking championship team, in his view, you know, it's you can let Masai

Ujiri walk out the door but you're gonna have a hard time replacing him and the credibility he brought to the Raptors from his perspective as a former player on multiple championship teams. What have we lost in your view? What have the Raptors lost in your view in losing you, Jerry? Yeah, I mean it's interesting because you could almost break it up into two categories. I do think like there's the basketball side of it. Well maybe let's get to that in a moment because I do think like Masai was bigger, is bigger than basketball in terms of what he represented for the Raptors. I mean, he became

so synonymous with the culture and the brand and justifiably so because he did so much work in reshaping it. But when people think about the Raptors, like they don't think about a player, with all due respect to Scotty Barnes, and maybe he'll get there one day, but he's not there right now. He's not the face of the franchise in the way that Masai Ujiri was. I mean a lot of people they associate the Raptors, rightly or wrongly, with Drake and with Masai. Players around the league, I mean even speaking to Elijah Martin, the Raptors second round pick yesterday over Zoom, he mentioned Drake and everybody talks about Masai because that's what you think of it now for various reasons. Drake has sort of distanced himself a little bit from the

organization and Messiah is gone so that's I think sort of what you miss in a sense and then also like I mean obviously the gravitas the performance every time that Messiah is in front of a camera it's just mesmerizing I think that was super valuable at one point it still is to some degree but, but I mean, obviously 10 years ago, that meant the world to this organization, to this fan base, to the city and country. The fact that he was so defiant of the notion that this market is anything less than the other 29 markets. He inspired a change in the way that other people viewed this market, sure, but his biggest

legacy is the way that he changed the way that this market viewed itself. So that part of it, I think, is going to be, his absence is going to be felt in that regard. But at the same time, like, look, I think thanks in large part to his efforts and his impact, I'm not sure that they need a public-facing representative in the front office in the same way. Like, Bobby Webster is super smart. He is well-regarded, well-respected around the league. He is very, very capable. They don't need him to perform for the cameras. They don't need him to pound on the table and tell us about how they're going to win again in Toronto. They need the basketball side of it. And

that to me is like, Masai has always been more than just the theatrics. He was at his absolute best when he was in a gym somewhere in North America or around the globe and scouting young talent. That's how we got to start in the league and connecting with people on a human level because he's really, really good at that. So that part of it outside of like just the larger than life personality, the actual basketball part of what he brought to the table is something that they're going to really met how much does life change now for bobby webster moving forward josh well find out

it pretty soon because it was confirmed today by keep telling question that i answered that bobby is going to be getting an interview for that president cd and i mean he better get it because if he doesn't Bobby is going to be getting an interview for that presidency gig. And I mean, he better get it, because if he doesn't, that creates a pretty awkward situation for everybody, because then all of a sudden, I mean, certainly he knows that he would have been passed over. And everyone else would too. We'll all know that he would have been passed over for the job and we'll have to report to the person that got it instead. So that's a pretty awkward situation in and of itself.

But then, like, let's say it is an external candidate that's coming in and getting this job. Well, first of all, I'm not sure how appealing that job is to people right now considering Bobby Webster, Dan Tollesman, the entire leadership team minus Masai, they're still here and they've been extended. So, somebody's going to come in here potentially and they're not going to be able to install their own people. It almost does feel like, I just finished my column for TSN.ca and I described it as

a house of cards where like right now, it's fairly stable in the sense that like, I have a lot of trust and a lot of faith in guys like Bobby Webster and Dan Tollesman. I don't think that this is a disastrous situation by any means. It's certainly not one that we couldn't have seen coming at some point, but it seems pretty flimsy right now, pretty precarious. And certainly on the cusp of toppling over if MLSE doesn't know

what they're doing and doesn't handle this the right way over the coming months. So Josh, today's news has obvious long-term effects on the organization, but when you think of the short term and how they approach this off-season and how they approach Tuesday moving forward with the free agency becoming an official, how does it change the course of action of the Raptors in trying to take that next step in becoming a team that is playing playoff basketball a year from now? I'm not sure it does to be honest because as I mentioned like the the team, the leadership team is still in place which means that the vision is still in place and clearly MLSE doesn't have a problem with the vision, right? Like, if they did, then Bobby

Webster wouldn't still be here, and then Masai also wouldn't have been allowed to monitor or have some say in the draft selections here. They would have brought in new people. And that's why, like, look, I'm pretty confident in saying the obvious here, the elephant in the room and something that Pete Peli could not say in a microphone is that this wasn't a basketball decision this was a business decision and that's perfectly fine and reasonable considering as we know basketball the NBA is a business but like first and foremost this was a cost-cutting move you mentioned Vladimir Guerrero earlier he's getting the money

that Rogers wouldn't pay Masai yeah there are teams that have been sniffing around Masai's availability, which is the case whenever his contract is coming up. And so he would have had quite a bit of leverage going into negotiations and surely would have been looking for another expensive new deal. He's already one of, if not the highest paid executives in pro sports. So like, I would have said that this was personal with obviously the history between Ed Rogers and Masai

and him reportedly blocking his extension back in 2021. If he didn't also sign off on the dismissal of Brandon Shanahan a few months ago, this feels more like, as I mentioned, a business decision than a personal one to where they're saying, like, it doesn't make sense to spend this kind of money on anybody in that position. And I would wager that whoever ends up in that presidency gig is going to be making a fraction of what Masai made.

So yeah, like I said, I think there's long-term ramifications here in terms of the short term. It sort of evens out a little bit where Masai and his reputation, his persona, like that would open a lot of doors for the Raptors, his Rolodex, that would open a lot of doors for the Raptors. I know like players, agents, other teams, like they respected him even if they didn't like negotiating with him. So it hurts in potential negotiations moving forward not to have him. Now look, I don't think they're going to be signing any major free agents anyways. They don't really have the money to do that. So I don't know that that matters so much here. But I also think when I say it evens out, I also think like the, that persona that I mentioned, the larger than life, all of that,

like the idea of Masai Ujiri scared a lot of people away too. There are a lot of rival rival execs that were jealous of him, that were intimidated by him. And I've heard rumblings of a number of transactions over the years, potential trades, potential signings, that were maybe broken up because teams that who you even know with James Dolan over the years in New York, that were broken up by other teams saying like, oh, I don't wanna deal with Masayi juries.

So maybe some more opportunities open up. Maybe some doors are shut. Who knows? We'll have to see how it plays out. Again, I think the optimistic view of this is that maybe it evens out. Yeah, for sure, Josh. I mean, you make a lot of great points there.

You look at Masai's job market now, that he's a free agent essentially although no one's crying for me is going to be paid well if he doesn't get work immediately sees under contract through this coming season with the raptors and we all know about the the payment that's going to be made or uh... based on the rise in the value of the franchise that he negotiated so

deftly back in twenty twenty one but if you had to make a guess of where Masai Ujiri might land in the coming months or even the coming year, what's on your mind? Yeah, well, we'll be just fine. The world is his oyster. So it really could be anything like he could, I mean, he could have a job today if he wanted one or he could take his time and wait and Handpick his next opportunity whether that's in basketball or outside of basketball I say outside of basketball like he could

Virtually do anything that he wants so not a bad situation not a bad time to be Masai Uchiri I mean as I mentioned like there are teams sniffing around he's one of the most highly regarded and still sought after executives in pro sports like look the luster has worn off a little bit since the championship at least in this market the last few years have not gone well but I'm not sure that's gonna matter to other teams when they look at his resume and they look at what he brings to the table. So yeah, if it ends up being something soon and it ends up being another NBA team, there aren't that many options. Atlanta is the one that keeps coming up.

They've been lurking, but I don't know that that's such a great job. I don't know that that's such a great opportunity. And Masai is nothing if not patient. So maybe he does wait this out and I think like one of the things that a lot of NBA people are keeping an eye on over the next half decade or so is potential expansion the NBA going from 30 to 32 like the NFL and there are a lot of interesting markets at the top of that wish list for the NBA. I know Vegas is one, going back to Seattle is another.

There are some potential options here in Canada as well. Vancouver, Montreal have been mentioned. So I wouldn't be shocked if he does go down the route of wait and see if he ends up starting somewhere, something from scratch, an interesting opportunity that maybe doesn't even exist right now. Well, Never Adul Day covering this team which you do very well for us. Josh, we appreciate you joining us on a new air for the Toronto Raptors with Masai Ujiri out. Enjoy the weekend and enjoy the beginning of free agency. Thanks so much guys, talk soon. There you have it, Josh Lundberg joining us on

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