OverDrive - Lewenberg on Webster's extension with the Raptors, leading basketball operations and the construction of the roster

Episode Date: August 18, 2025

TSN Raptors Reporter Josh Lewenberg joined OverDrive to discuss Bobby Webster appointed as the head of basketball operations, the tasks and duties with the role, the external options in the process, Masai Ujiri's departure's ripple effect, the stance of the team, the foundation of the roster and more.

From tariffs to trade deals, the markets are changing. Is your portfolio ready for what comes next? For all your questions, you need a money guy. Kelvin, the money guy, will help you develop a financial plan that includes the right levels of diversity. The best way to navigate uncertain times. With strategic advice from Kelvin, you can not only protect your investments, you can grow them. Don't wait. Call 416-457 plan or visit ask kelvin.cai.a.

Claudia was leaving for her pickleball tournament. I've been visualizing my match all week. She was so focused on visualizing that she didn't see the column behind her car on her backhand side. Good thing Claudia's with Intact. The insurer with the largest network of auto service centers in the country.

Everything was taken care of under one roof and she was on her way in a rental car in no time. I made it to my tournament and lost in the first round. But you got there on time. Intact Insurance. Your auto service ace. Certain conditions are.

apply. Josh Loomberg, our TSN Raptors reporter. What's going on, Josh? Not much. How are you guys doing? Doing well. The Raptors gave us a nice spicy topic here to chat about on a wonderful Monday. Bobby Webster named the president, or not named president, rather named head of basketball operations. What exactly does that mean, Josh? Yeah, probably not a coincidence that they fired Messiah on a Friday and then they promoted Bobby on a Monday. But, yeah, I don't know if we can call this a promotion, maybe a quasi-promotion in the sense that, yes, it comes with new responsibilities. It sounds like a new contract and probably a nice raise, more pressure and all that. But while Bobby gets Maasai's old job, he doesn't get the title, as you mentioned.

He's going to be running basketball operations from the GM spot, and they're not going to hire a president for now. it's not entirely unusual in the sense that, like, look, team president is not even something that really existed in this organization up until, like, barely recently. I think Brian Colangelo comes in, and they kind of, it was a big get at the time. They need to dangle a fancy title in front of him. Even Maasai, when they brought him back, and that was obviously a huge coup by Tim Lywicky in 2013, he wasn't the president when they hired him. he was by title the general manager and ultimately was elevated to president.

I think it's about half of the league right now that is operating without a designated president, including, by the way, the reigning champs, Sam Presby for all of his many accomplishments and he's been there forever. Technically, he's listed as the GM, and he, like Bobby Webster is about to do, reports to ownership. So every team, every sport has different structures. and hierarchies in the front office. I don't think it's entirely unusual. And it's actually a solution that I floated last month.

I can call it what you want, maybe a half measure. I kind of think of it more as a compromise where the sense that I got pretty early in the process is that MLSC wasn't convinced that Bobby Webster experienced, but still young as an executive, they weren't convinced that he was ready for the president gig. Now, that's kind of reflected in the fact that they, did this extensive search, and it's certainly reflected in the end result here. But if they weren't enamored with any of the external candidates, and they interviewed a number of them, including, as I understand and has been reported as well, Pacers GM, Chad Buchanan, Bulls, GM,

and Canadian, Mark Eversley, and then, of course, a name that Raptors fans are familiar with Dwayne Casey, who, I'm told, met with MLSC three times last month. If they weren't enamored with any of the guys they could get with, what, I understand it's a pretty modest budget, then this allows them to continue grooming Bobby and Dan Tolstman and see how it looks. Like, they can see how these guys do in their elevated roles, ultimately see how this team that they help build fares this season.

And if they don't like how it looks, they still have the flexibility to pivot. I think there's a reason why this new front office hierarchy is etched in pencil and not in permanent ink. I think that a team that, as I described it last month, had a lot of nervous energy around it. A lot of these guys can take a bit of a sigh of relief, breathe a sigh of relief, but none of them are safe in the sense that, like, I think this is still very much a fluid situation moving forward over the next few years. So, Josh, we were just talking Al's brother and I about how this sort of reminisce it in some ways

of the massive extensive search that took place in the wake of firing Dwayne Casey and they're all kind of candidates considered to take over the head coaching position and then in the end they went with the guy that was sitting next to Dwayne Casey and Nick Nurse. And of course, Nick Nurse defied every expectation and was a very different coach than Dwayne Casey

even though he'd been sitting next to Dway in all those years. I mean, knowing what you know about Bobby and what you heard today on the conference call that he conducted with various members of the media. How do you think Bobby might be able to differentiate himself from Messiah Jerry? Yeah, no, I love that comparison, and it's one that I used in the story that I wrote last month and making the case for Bobby, because I think the assumption that people are going to make here, the same assumption that was made when nurse was hired is that, like, okay, well, you've got

two people that have been working together for a very long time. You get rid of one of them, which probably means that you're at least looking for some semblance of change, why are you bringing in his top lieutenant? But I think what that proved is like, despite the fact that they had worked very closely together for many years, as we later learned, I mean, Nick Nurse and Dwayne Casey are two very, very different people with very different quality, strengths, weaknesses, all that, and certainly two different visions and coaching styles. Now, I don't think that this is going to play out quite in that way in the sense that look like i think bobby's vision from a basketball

standpoint it is probably pretty similar to massize i don't think they were lockstep on every decision that was made but i mean even on the record bobby has spoken over the years about valuing the same type of players that masai does the long athletic versatile wings that may or may not be able to shoot so i don't think like from that standpoint we're going to see like a drastically different team. But what's interesting, what I was told was that a number of the external candidates that came in really, really pushed back on some of the moves that Maasai and company made over the last few years.

One of them went as far as calling the Ingram trade a desperate Hail Mary. And that's not surprising, right? Like, I think a number of them also pointed out the fact that the Raptors are in a bit of a cap crunch and paying a lot of money for a team that kind of tops out right now. now as a play-in group. So the fact that they ultimately decided to stay in house tells us a few things. I mean, first of all, it reiterates what we already knew and that the Maasai firing has more to do with money than vision.

But it also tells us that this new look ownership group, led, of course, by Keith Pelley and the Rogers Control Board, that they still believe in this team. But, yeah, I mean, I think ultimately it's going to come down to what happens on the court this season, whether this vision that Masai had that is probably inherited now by Bobby actually works, where I do expect to see some changes or at least some differences is a lot of the behind-the-scenes stuff that might not be reflected in the roster in the sense that, like, while their vision might not be entirely different, these are two very, very different people.

Like Maasai's, we know, larger than life, personality and persona, Bobby's not that guy. And I don't necessarily mean that that's a bad thing. Like, I think he's more understated down to earth, certainly easier to relate with. Like, Maasai, I mean, over the years, he became a celebrity. And I think there are just certain things that go with that, whereas Bobby, like, he can dress down. He's still young enough to relate to a lot of the players and fans and just people around. like he can chop it up with anybody, whereas he could also put on the suit and he's highly regarded and respected by his peers. I think he's shown over the years that he's certainly very capable

and more than just the like cap manager that a lot of people kind of typecast him as when he first got here. So I think he's certainly deserving of the opportunity to show what he can do, but I don't know, like, he has been involved in everything that the Raptors have done. The Missouri has done over the last decade plus, but he hasn't had final say on any of it. So, yeah, like a lot of people, I'm interested to see what a Bobby Webster-led front office and what a Bobby Webster team looks like. Well, like, does this change, I guess, like, the expectations moving forward, like for this team, whether it's this year, the year after?

Like, is there anything that changes from what the ownership, expects of this group with this change? Yeah, again, like, I think it speaks to the fact that ownership is completely behind the current plan, and the current plan, as far as Maasai Ujiri left it, was to push forward, right? Like, the rebuild is more or less over. They've gone all in on Brandon Ingram and more or less all in on this court, because, again, very expensive group, I think it's the eighth highest payroll in the NBA, despite the fact

that they've won a combined 55 games over the last two years and have the 22nd highest win projection going into this season. So, yeah, I mean, Maasai believed that this team was ready to take the next step and to compete for a playoff spot in what is a very diluted Eastern Conference this year. And the fact that it's kind of status quo here in terms of the front office tells us that at least in the short term, that's the goal, that's the expectation. But, yeah, I mean, like I said, it's such a temporary solution that if it doesn't work, they've left a lot of room here for change. Well, I'm just curious, though.

So if they're happy with, you know, the work that Messiah and Bobby have done, they want to move forward with this direction. Like, doesn't it kind of make it, I don't know, a little more confusing as to why they moved on from Messiah in the first place then? Yeah, I mean, it was confusing then in terms of the on, the record explanation given by Keith Pelley at that press conference. But I think we all have a pretty good idea of why the move was made. I mean, there are some people that subscribe to the idea that it was something personal between Edward Rogers and Masayu Jiri. I don't really subscribe to that, at least not fully, because, I mean,

Masayu Jiri isn't the only president that MLSC has moved on from over the last year. Bill Manning on the soccer side. and then, of course, Brendan Shanahan on the hockey side. And by the way, neither of them were replaced. And that's why I think it was certainly wasn't surprising that they moved on from Masayu Jiri, given his contractual status, both that he was up for a new contract and probably an even bigger payday, but also his current salary pays him a base salary of $15 million annually. And while the new deal for Bobby Webster is like the details and the terms are not disclosed,

I would, I think it's safe to assume that he's making a fraction of that Masay Ujiri salary. And that's maybe why they weren't able to attract more interest and more bigger names in their search for this position. If they weren't willing to pay top dollar, then yeah, I mean, I heard the name Kevin Pritchard. the Indiana president as somebody that they were interested in. But if they weren't willing to pay top dollar, how are you going to lure someone in a lateral move, a lateral position over from a team that just made it to the NBA finals? You know, so I think ultimately you kind of get what you pay for.

The budget was what it was. And now, as I said, this allows you to groom some younger people and people that you're familiar with. It also reinforces the plan here. It's just, I think what's unclear at this point is like, what's the ceiling here? What's the long-term plan? Okay, this year you push for a playoff spot, certainly a play-in spot, very, very doable, again, given the Eastern Conference.

But like, I don't know that anybody is looking at this roster and saying, okay, well, this is a team that's going to compete for championships in the near future. Scotty Barnes continues to be the ultimate wild car. there where like if he goes to the moon this season, if he explodes and really develops as a top 10, top 15 caliber player in the NBA, that all of a sudden we have to rethink that ceiling. But again, based on what we've seen over the last year, Scott, he's a really good player. Brandon Ingram, really good player. But I don't see that kind of trajectory, at least right now, from any of these players,

meaning you're stuck with a very expensive, very average team. And outside of the one guy at the top who's been relieved of his duties, this entire leadership team remains the same. And that's why I wrote last month, like being around this team in Vegas, a team that is almost entirely intact from what it was last year, a lot of nervous energy. So, yeah, I mean, it's a very strange situation. I can understand, again, given like the Bill Manning and the Brandon Chanahan of it all, why they ultimately decided to put off hiring a president with the basketball team as well. But I think this is going to be kind of an approve it type of year, not only for this team, but for the guys running it,

because if things don't go well, then I would be really, really surprised if the front office remained largely intact at this time next year. Well, Josh, that's a great way to put it. I interpret it the same way. It's a prove-it kind of deal for Bobby Webster, almost dangling the idea that you could be president one day, but you're going to have to show us that you deserve to be president. And by doing, you know, to do that,

you're going to have to make this team relevant again competitively, which they haven't been for quite some time. And I'm wondering, Josh, when you think about money here, and money is central to this whole, And when we're talking about the disappearance of these presidents and a lot of other things that are happening around Mapley Sports and Entertainment, this is a team, as you point out, that's got a really high payroll. You know, they're paying premium prices for a lot of these players. If you're Bobby Webster and you're in line to be a tax team right now, the way it's sitting, I mean, you probably have to cut some of that, right? And where do you go to cut some of this payroll if you're kind of reading the tea leaves of you don't want to be a mediocre team?

with a championship expense payroll? Yeah, well, more often and not where there's smoke, there's fire. Not all the time, but certainly a lot of the time when it comes to trade rumors in the MPA. And we've heard the name R.J. Barrett quite a bit this summer. And again, I think there's something there in the sense that he's a guy that kind of become a bit redundant on the roster with the addition of Brandon Ingram. I know there's been a lot of concern about like, okay, well, how are Ingram and Scotty Barnes going to coexist on the floor?

And sure, there are some questions there, but I think the bigger question is, like, how are RJ and B.I going to coexist on the floor, similar positions, occupying similar spots on the floor with similar strengths and similar weaknesses? And to all, like, to RJ's credit, I mean, he has really increased his value, I think, in terms of, like, the quality of player that he is during his time with the Raptors. He's really impressed, I think, here, but has. become an expendable piece, especially considering the salary situation and the fact that he's got only a couple years left on his contract, whereas all these other guys are under contract for longer term. So they've got to make a decision on him. I think the good news here

is that despite the cap crunch that they're under, you can go into the season even a little bit over the cap as I believe they are right now and still have a few months to figure it out. Ultimately, tax doesn't get charged until game 82. So while I think they're more or less done right now, in fact, I know that it's one of the things that they told not just Bobby during the interview process, but all the external candidates as well is that this decision is made for the future, at least the near future, that right now there's nothing to be done. The roster is set. I don't expect any big moves to be made before training camp and and before opening night, but if you told me that R.J. Barrett was moved at the trade deadline

or even somebody like Ochia Abaji, if they really wanted to nitpick and get under the tax by moving a smaller salary, there are moves that are going to need to be made here, especially if this team doesn't excel and really get off to a hot start. So I do think, like, that's one of the reasons why you want Bobby Webster around. Not to say that he's the only guy that's good with numbers, but he is a guy who is very, very good with numbers. That's his background in the NBA coming from the league office where he helped create one of the previous CBAs. He's really good at kind of figuring things out in that regard,

and I think he can have some confidence in the fact that he'll figure out a way to shape the roster to potentially avoid the luxury tax, but at the same time, like, there's only so many small moves that you can make to change what is a really tough financial situation that the Raptors find themselves in. So while that's a strength that he has, I think, again, he's going to need to demonstrate a few other strengths in terms of his eye for talent and his ability to make some savvy and shrewd moves here to get this team over the top.

Well, we'll see how it all unfolds, Josh. We'll see how it all unfold to be a fascinating upcoming season for the Raptors. Appreciate the time, as always, pal. All right, guys. Talk soon. Absolutely. Josh Lumbert, our TSN Raptors reporter. Seasoned gamer, or just video game curious, this week in gaming is the podcast for you. We break down the latest in the world of video games, from basics to beyond. The hottest gaming news, insight, and industry leaders, and more weekly.

Join me, Naomi Kyle, and stay ahead of the game with all the latest updates. Even if you're a total newbie. stream this week in gaming on the free iHeart radio app or wherever you get your podcasts