OverDrive - Lewenberg on Webster's management tasks, Ujiri's replacement and the Summer League roster

Episode Date: July 9, 2025

TSN Raptors Reporter Josh Lewenberg joined OverDrive to discuss the headlines around the Raptors' offseason in Toronto, Bobby Webster's tasks for the team, the replacements for Masai Ujiri as president, the Raptors' Summer League roster foundation and more.

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The station that champions Canadian music. Loud, proud, and all yours. No passports required. Just press play. Tap into Made in Canada now on iHeartRadio.ca or the free iHeartRadio app. Our Raptors insider, Josh, welcome. How are you? I'm happy to report, well, I'm good now.

Happy to report that yes, I will be heading to Vegas. Didn't look so good a few hours ago when I went to check in and realized that my passport expires tomorrow. But yes, fortunately I have a new one. Everything is done, everything is settled and I will be in Vegas tomorrow. I mean, how did you get that passport done right away? He's an important man, Tati. He knows people. Yes, they rushed it just for me. No, apparently it happens. They said no big deal. They deal with

it every day multiple times fairly about the first one or the last person to allow this to happen to myself i'd just hope that when you're on the other side of the border things are ok it might end up in the news somewhere but anyway let's move along so well without without that with the change at the top without miss a jury

and how do you think this thing tracks for is going to be drastically different or status quo? I mean, it'll be interesting to find out. Well, first of all, we're going to have to find out eventually who's running the show. Like right now, we know that it's Bobby Webster in the general manager position, but at some point it sounds like the plan is to hire a president. We know that Bobby is going to get an interview and be considered for it. We talked about this back a few weeks ago that the dynamic internally, if he gets an interview,

doesn't get the job and then has to report to whoever does get the job, could be pretty awkward. And I'm not sure that that's a sustainable working environment. So let's assume that at least for the foreseeable future that the basketball decisions are gonna be made by Bobby Webster. I mean, I think the assumption that a lot of people will make is that Bobby is a guy that has been the top lieutenant for Masai for many, many years now,

will have a similar if not the same vision. And certainly the early returns would suggest that as well. I mean, Masai believes that this team is ready to make the next step, to take the next step. And he also believed that Yaka Pertle was gonna be a significant part of that, an essential piece in making that happen. It's why just about every time that anybody has checked in on Yaka Pertle over the last year plus, he's

turned them away. The Lakers were interested at the trade deadline. Masai said no. And when they were talking to Phoenix about Kevin Durant over the last couple months, Phoenix was interested in Pertle. Masai said no. So the fact that Bobby was the point person in making this contract extension that was reported obviously last week and became official today, that was Bobby that kind of took it over the line. But of course, Masai has had a lot to do with not only drafting Pertle, bringing him back here and putting him in position now to get that extension. So it would seem as though the vision remains alive with Bobby Webster and this leadership team that has worked so closely with Masai over the years.

But I would caution with that assumption just to say that like, I think that's what a lot of people assumed that was going to happen when Nick Nurse took over for Dwayne Casey. It's like, okay, well, if this team needs a new vision, why are you promoting the guy that worked underneath the other guy? And the irony, of course, is that Nick Nurse couldn't have been more different from Dwayne Casey, both in terms of approach, coaching style, personality. And I think we might see something similar here too in the sense that yes, Bobby has worked very closely with Masai. He has been involved to some degree in every decision that has been made, but he has had

almost no autonomy in those decisions, or at least he hasn't had the final say in anything. So I'm really interested to see what a Bobby Webster run team looks like, what his philosophies are and ultimately where he sees this team going. And I think we'll find out here if not immediately over the next few weeks and months because I do think this roster is pretty much set. Certainly over the next few years if this reporting structure remains the way that it is, I hope he gets a shot because like I said, if nothing else I'm interested to see what he does in the main chair, in the main seat. I think he has earned that chance and I think if he doesn't get it here, he's going to get it somewhere.

He's become one of the most highly sought-after executives in the league i know chicago was sniffing around before they ultimately ultimately hired a former after exec mark ever's lee a few years ago other teams have been sniffing around as well so i think he's earned this opportunity and i'm excited to see what he does with it josh when you look at the you know the landscape and you have a search firm brought in to find a replacement for Masai Ujiri, it's the CAA executive search firm affiliated with the CAA agency. CAA runs the NICs right now, essentially.

We know how incestuous that business can be. There are really qualified presidents out there without current work bob meyers obviously uh... one of the linchpins a building the uh... step curry dream on green clay thompson warriors is out there currently working in the media a yanny a sense of who else might be in the running i mean bob miers be expensive ticket

cost would you probably come into the there, but you getting any sense of who else might be on the radar? Yeah, let's start there because like that's the name I've heard pop up a few times, not like from anybody inside of the league, but just in terms of like people speculating because yeah, that's the biggest name that's out there. First of all, like I don't get the sense that he's interested in leaving what seems like a pretty cushy media job right now to get right back into it, at least at this point. But beyond that, the most important thing to consider here is the other factor that

you mentioned is cost. He would not come cheap. I don't know that it would be quite at the level of the size reported, what, $15 million a year salary, but it would be pretty darn close. And we talked about this after the Messiah firing, is like, they could justify it however they want. And to be fair, Keith Peli didn't really even justify it. He didn't have an answer to the why was Messiah let go question, because the answer to it was money, cost. I mean, Pelly was pretty clear in that like from a qualification standpoint, Masai

is at the very top of the executive hierarchy. Like it doesn't get much better than that. He checks off just about every box that you would want from an executive except for affordability at least in this case. So it's a pretty safe bet that whoever they hire to replace Masai is going to be paid a fraction of what Masai was getting paid. So I think that crosses Myers off the list initially. So it's probably somebody that not a lot of people have heard of, maybe not like a household name brand, maybe somebody that's younger, not quite as experienced. What interests me is you mentioned what we've seen in New York over the last few years,

but even around the league, like the trend in this modern MBA has been agents turned executives. We've seen a lot of that recently including Bob Myers. So I wonder here if you look at the Raptors front office and they have a little bit of everything. I mean Bobby has a lot of experience unlike the CBA side of things, tactically, strategically, they have people that have played the game before. I think you need that perspective as well. They have people with scouting backgrounds. The one thing that they don't have that a lot of teams have now and seem to be working pretty well is that agent perspective. So I wonder if

that's something that they would consider. It's something that I have heard in league circles that a few different names have popped up. People that have experience working individually with players like agents would have. And I think that that's something that could be a possibility if they don't go the internal route that Bobby Webster went. Josh, the Summer League kicked off in Vegas a couple of days ago. Raptors, they got their first game coming up on Friday against the Bulls. What expectations do you have for the Raptors this year at Summer League? I mean it's a fun team. It's stacked from a Summer League perspective. I

think there's seven players on this Summer League roster that suited up for the Raptors last year, which tells you a couple things. One, this is pretty good for a summer league roster, and two, a lot of guys suited up for that Raptors team last year, and that particular team wasn't very good. But I like the fact that we're going to see a lot of guys that have NBA experience that are going to be a part of this young core moving forward. I'm not sure how much we're going to see of them. Like I know for the real basketball nerds among us is like okay well this is a team that could win the summer league if that sort of thing interests you. I don't know that they'll ever be in position to do that because it's something that we've seen over the last few years with players that are part of the NBA rotation

or have NBA experiences, they generally play the first few games and then they shut them down pretty early. So like Jacoby Walter, who was already dealing with injury issues last year, like I'm not sure how far they let him get into this tournament. Jamal Shedd, same thing, even prized rookie Colin Murray Boyles. But for however long it lasts, I'm interested to see what those guys look like, particularly CMB. I mean, Murray Boyles, I think that was a surprise pick for a lot of people, including apparently Colin Murray Boyles, given his reaction.

But he's an intriguing player. And it's somebody that I'm not sure how well his game will translate to the Summer League in that like You've got a lot of guys in the Summer League looking to take a lot of shots put up big numbers And he's a guy that is pretty good on the margins does a lot of the little things well the hustle things defensive plays and I'm not sure that's gonna show up necessarily in summer league but uh... interested in getting a look at him seeing

on how to call be looked after the first part of his off season uh... yeah and i think they're gonna have uh... pretty decent shop for a long as those guys play could be fun gosh you know as i look at this lineup and i would see the words of big names that were out there that the rafters were interested in and that didn't happen but this is a deep roster is it top heavy is it I mean the second unit the third unit everything looks good there but is there

a trade? Well yeah in terms of the depth this is as deep as I think this team has been since just well I was going to say just before the championship when they consolidated a lot of those depth pieces in order to go out and get Kawhi and get Marcosal. But, I mean, let's not sell the championship team short because even once they made those trades that was a pretty deep team in and of itself. But certainly that has been a weakness that has been an area of need for this organization over the last few years is depth and to their credit they've done a pretty good job especially in the draft last year of finding guys that look like they can be contributors to a winning program we don't know that they will be necessarily

just because Jamal Shedd looked good in games that they were trying to lose in the second half of last year and that Jacoby Walter looked good in a small sample every time he was healthy but was not really healthy all of that much. So I'm going to be more interested to see now that to your point, like you've added Brandon Ingram, presumably guys are going to be healthy this year and all of a sudden somebody that might have been starting last year, let's say like Grady Dick for most of the year is now all of a sudden not only coming off the bench, but he's going to be fighting for minutes with Jacoby Walter

and with Ochai Abadji. So this is a good problem for Darko Royakovic to have, assuming that all of these guys develop at the rate that we've seen so far. That's another reason why summer league is intriguing to see where these guys are at, kind of halfway through their offseason. To your question about the trade, yeah, I mean, the Raptors have been front and center in trade speculation up until this point. I don't think it's a coincidence that we were hearing a lot of noise, a lot of smoke

in the lead up to what turned out to be Masai Ujiri's dismissal. I think it's kind of hard to nail down the timeline of how things happen and when things happen. I mean, I've heard different stories even just from what we heard publicly from the MLSC side from Keith Pelley at the press conference that it's something that's kind of been in the works for the last two months and that Masai has been aware, maybe not of the date that something was going to be happening, but that something was going to be happening for about a month. And again, like the timeline, I'm not sure specifically that that's how it happened, but it does sound like Messiah would have had some sense that change was, if not imminent,

likely or at least a possibility. And that's why you wonder, like, was he trying to maybe save his job by taking a big swing, by going out and potentially landing a Kevin Durant or John Adedekumbo, the ultimate pipe dream? It has quieted down. Yes, since the firing of Masai Ujiri, but I just think in general, now that the draft has passed, it's a bit quieter around the league. The one name that keeps coming up is RJ Barrett, somebody that, yeah, I mean, I think the Raptors

have been shopping to some degree leading up to the draft, probably will still continue to shop to some degree leading into the season and even during the season for a couple of reasons. I mean, right now, the Raptors roster is almost full and they're projected to be a little bit over the tax. I don't think they are gonna want to pay the luxury tax for a team that is currently constructed is probably projected to be a play-in team. Now they do have until the end of the season to get under the tax so maybe that's something that they look to do at the trade deadline. At least you go into the season get a look at this group see what

they're capable of and then pivot from there if needed. But also specifically in terms of RJ, and this is why his name keeps coming up, is he's got a couple years left on his contract. He's eligible for an extension right now. I think it could probably talk him into waiting it out, playing out another year. But certainly if you let it come to this next summer,

he's gonna be expecting an extension. And just based on how expensive this core is, they're not going to be able to pay him. So at some point they've got to make a decision there. I don't get the sense that there's a ton of league wide interest in him. I mean, it's kind of obvious to say if there was he probably already be gone. And in a way it's sort of unfortunate because I do think he has shown that he is a better player than a lot of people thought when he came here from New York. I think his value has gone up. But and I think this is the case in life too. It certainly in a lot of professions is once you've got a reputation, once you've got a label, that's kind of the way that people

look at you. It's kind of hard to shake that. And rightly or wrongly, he was kind of known as somebody who was a negative asset. And I don't mean a negative player, but a negative trade asset before the Raptors traded for him. And even though, like I said, I think he's done a lot to raise his value, there are still probably a lot of teams that are looking at him and saying, okay, well, this is a neutral asset at best.

So I don't think they're not going to move them just for the sake of moving him. And unless there is an interesting offer out there for him and you're actually getting something back for somebody that, I mean, was a major contributor for them last year, I think he kind of ride it out for now, but at some point you've got to make a decision when it comes to our gym. Josh, thanks very much. And best, best travels, best of luck in the travels. It can't go anywhere that has gone to this point.

Phone's always on. Just give me a call. I'll set it up for you. All right, guys, take care. Josh Lohenberg, Vegas bound. Seasoned gamer or just video game curious? This Week in Gaming is the podcast for you. the game. all the latest updates, even if you're a total newbie. Stream This Week in Gaming on the free iHeartRadio app or wherever you get your podcasts.