OverDrive - Armstrong on the Raptors' roster expectations, Webster's point of view and Ujiri's replacement process

Episode Date: July 9, 2025

TSN Basketball Analyst Jack Armstrong joined OverDrive to give his perspective of the Raptors' offseason moves, Bobby Webster's philosophy on the team, Jakob Poeltl's extension in Toronto, the emerging players on the roster, Masai Ujiri's legacy and the replacement process, LeBron James' future with the Lakers 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 Jack has just completed his 18. I'm sure he signed a scorecard and it's all official. Jack Armstrong is with us now Jack, how did you shoot?

I did okay. We had a good time out here today. I'm actually looking at Toronto right now I'm I'm at Toronto right now. I'm at the Niagara Falls Country Club, which is my club. It looks out on Lake Ontario and the Toronto skyline. So I'm looking at you guys right now. So it's all good. Oh, good to know somebody's out there. I'm waving, Jack.

I'm waving back. I'm waving. What do you make of the Raptors offseason to date? Well, it's been quiet. What do you make of the Raptors offseason to date? Well You know, it's it's been quiet Obviously other than the departure of Masai Ujiri from a personnel perspective It's it's been quiet You know, it was pretty obvious they were going to resign a yaka Pertle

You know their draft picks were solid obviously Definitely geared towards a defensive focus signed a Yaka Pertle. You know, their draft picks were solid, obviously, definitely geared towards a defensive focus. And beyond that, I mean, the biggest, the biggest news is, you know, Messiah Yajiri's departure. But, you know, I think when you look at Bobby Webster and Dan Tollesman, those guys are, you know, obviously are you know obviously uh... guys have worked day in day out for a long period of time of the side

so i don't think it i don't see things changing that and we lost them value bill i think what i think we should we should just by sorry jack where a problem here let let's reconnect with him because he's in and out and I don't know exactly what everybody's hearing or what he's hearing so we'll reconnect with him. And his point is kind of a status quo off season for the raptors which we would agree with.

There was all that talk before Messiah left about big name hunting and it's not going to happen apparently, right? So I don't know what the expectations were because where they were and where they're projected it's okay it's okay and just okay a phrase from a former Maple Leaf coach it's hard to get excited about this team because we just we don't know enough about this team and I guess Jack the question is when you started we've been we've been hearing some of the US pundits take shots at

the raptors for rebuilding this roster players that are very highly paid and yet also quite unproven especially as a group because they have played in a much as a group i mean when you look at the collection of talent flash payroll that they've accrued here and how do you look at it

i look at it this year that i i think they're going to be a uh... team that uh... makes it the next step you know me being a kind of a five hundred type team maybe a little bit better uh... play and playoff type team i think you had a branded anger you know you had a group

and uh... i think if you add a Brandon Ingram, you know you add Ingram and I think if you get a quickly healthy, I think Scottie Barnes will be much better. I think all the young players got a ton of playing chemistry. Coach Stalko has respect of this roster. They play hard for him. They buy into what he's doing. There's a style of play. There's a personality. I think a big part of it is going to be how Ingram kind of meshes. Sometimes the ball will get a little sticky in his hands, but he's a terrific scorer. So they're going to have to kind of figure out how to have him mesh with the group. To me, you know, there was a lot of

discussion with RJ Barrett be back or not, and to me, I think he's played really well. I'm a big RJ Barrett fan. I think he's really improved since he's come to Toronto, and I'm curious to see. Okay, well, we're going to have to do that again, the reset. Unfortunate that that happens. A country club cell service. Yeah, it's not enough bars. Apparently not. Oh, there's a good bar at that.

I've been to that country club, there's a very good bar. I know, but not enough of the right bar. I think Jack is probably about to go to it once he gets off the line with us, which he may be off. We may drive him to that. Yes. I wouldn't blame him. But you know what, you know, the Jacks,

like I sort of see it the same way as Jack. I know people have been saying the Raptors are in a really bad spot because they're committed to all these guys, you know, and really haven't got much to show for it today. But it does feel like, like, let's face it, last year was a tank year by design. They didn't do a particularly good job of it because they didn't get Cooper flag. But Jack, you know, let's face it, last year was a tank year by design. They didn't do a particularly good job of it

because they didn't get Cooper flag. But Jack, we were talking, sorry, we've been having a hard time hearing you because your cell's in and out, but you're sort of making the case that this is a bit of a next step year where they can build into something a little more respectable in the 500 plus range.

We left off at Inram but could go from there in and why you make the case that this this is a team has a chance to do you're saying it's going to do well because i think uh... it is a manual quickly health uh... scoring who can shoot the ball stretched a floor. I think they're gonna have options in terms of their second unit they're gonna have great depth. Have 11-12 guys who can play. I think during the course of an NBA season to have the ability to have depth where you're going to have injuries and sickness and all the other things, they have kind of rebuilt of the organization.

So I think they're at a point right now where they should have every right to feel like, now I'm not saying they're in the top four, but that next group, I don't think they should feel any bit intimidated by taking on anyone in that next tier of Eastern Conference teams. So to me, I think a lot of it's going to come down to getting off to a good start, being healthy and developing that chemistry and kind of getting a guy like Ingram quickly as a guy that's going to be huge for them. You know, I'm a little concerned with how the games are being called right now in terms of perimeter.

They're loosening things up a little bit. He's a little slight and he's going to have to be able to play through contact a little bit more more about finesse scoring minded point guard but nonetheless i think if he is able to adapt his game and and a guy like ingram i think they could make it a definite

significant step jack what's the strong belief i guess in a player like yaka portal with him within this rap is front office like there are many reports that he was off limits in any kevin durant trade discussions like what is it about him uh... that makes him so indispensable for this team well i don't know if he's off limits i i you know i i think when you look at it if they had a chance to get kevin durant and that was going to be in play and i think they'd reconsider i'm sure they knew what the market was for Durant and whether they could really get him or not.

And you know, you hold things back, obviously, when you're trying to do a deal, and then you throw it in when you know you might be close to getting it done. But a guy like Jacob Pertle, you know, he's,'s looked at this some debate on the back end of the deal whether that's gonna uh... be a good return on investment on the back end but on the front in the first few years i think they'll get great return the guys uh... uh... terrific sound defensive player

you can run a lot of pick and roll with him you can run a lot of actions with him in the mid post he's a good player and he's a tough-minded, adorable, team guy, understands what they're trying to get accomplished. So to me, I think sometimes you got to, you know, when you have a guy that you trust and you like and you believe in and you know you can count on him night in night out maybe you pay him a little bit more because this is a guy that's part of what you're trying to build and he's gonna now is he gonna be your but when you talk to the third guy fourth guy fifth I it's all part of

putting it together and when you have a lot of young players that are on a deal, you can pay at a little higher number. The question is going to be when some of those young guys, the Grady Dicks, the Jacobi Walters, the guys like that, their number has to come up. Those are the decisions that become difficult. So, Jack, you know, in doing the games last year we were all thrilled. Everybody had to step up in terms of the young players and a lot of them, I'm not going to say we're overplayed but we're elevated to a level that we found out they could actually

handle. But now comes the tricky part is you have to sort of back them down and cut their minutes down and get a little more specific about what you need out of the young players like Grady Dick and Walter and I can just go there's about five or six of these guys. How tricky is that? Jim, it's a great question because it's a challenge of pro coaching quite frankly because now you've got to manage egos and when you have so many guys in and out of the lineup everybody's getting a lot of time and a lot of touches so everybody's happy now if you have a relatively healthy group you're going to have some

second unit guys that are playing for second contracts down the road that will you know will have the natural inclination to want to play more, want to shoot more, and develop numbers because the numbers are insane in the NBA right now. So that's a big challenge now for Coach Stalko in his third year, being able to manage all that. And again, you're bringing a guy like Ingram in, who you've paid a lot of money to, you made a big deal to get. And again, you're hoping quickly he's healthy. Those are the challenges you have right now.

And look at a guy like RJ Barrett. Where do his shots come from? What role does he have? Is he better suited maybe coming off the bench a little bit ward you know who's your starting five is it your best five or your five best and and that's always a challenge in terms of trying to figure that out but to me

i think they're talent-based has gotten better the question is going to be that it all come together the uh... may please sports entertainment folks have hired a search firm, CAA's executive search to go out there and look for the next Raptors president, the successor to Masai Ujiri. You'd be my choice, just so we're clear, Jack.

You'd be my guy if i was heading this search but if anything and i'm sure you're you're probably very interested in that job but you got a great one as it is but it's not you jack uh... any any idea of of who they may tab or who they should tab to uh... take over the reins from the side well they thank you for the kind comments uh... nobody's come to me about it and I'm very

happy doing what I'm doing. But the check's in the mail Dave, thank you so much for that kind commentary. I'm very happy doing what I'm doing. In my opinion, you want to, if you're going to go outside, if you're not going to promote Bobby Webster to President and Dan Tollesman to GM, if you're going to do that, that's great. If you're not going to promote Bobby Webster to president and Dan Tolesman to GM, if you're going to do that, that's great. If you're not, then I would say that you want to get somebody that has a kind of a little different worldview in terms of how you build a team and you know how things are. I think we've seen a lot of success in our business of late where you have a guy that's been an agent That's been able to kind of you know, because Toronto it's all about not only recruitment

It's retention and referral. So to me, I think that's a big part of it You know you look at the success that a number of guys have had in that role big picture oriented or do you bring in someone you know that's a former executive you know a GM or you know someone that has run the whole operation and you know again what's the commitment what's the dollar figure what's the term all those things come into play and it's interesting you look at what's happened with figure, what's the term, all those things come into play. And it's interesting you look at what's happened with the Leafs, they're not

going to do a president, they're going to stick with basically replacing Shanahan and just going with a GM coach format. So it's a little different. But to me, I think if you're going to go that way, I think you have to look and say, okay, I've had the same people here for a long time. Maybe I need to get somebody in here that looks at things a little differently. If you're not going to do that, then you might as well just promote Bobby Webster to president and have Dan Tolman as your GM. So I think those are the choices right now for Keith Kelly.

And again, when you look at search firms, all they're doing is they're vetting candidates and then presenting a few different options to your board. And then those are the people that have to make the decisions because they have to be the sports experts not not your search firm. The search firm only presents people you have to do all the rest of it Jack I like what you said there. I mean clearly under one aspect of you if you promote Bobby Webster you're maintaining and if you bring somebody else in its fresh eyes and different look and and maybe there's a lot of transition that

follows. I guess the only question that comes out of this is because Masai was was so present almost as a front office type a really good sort of face of the franchise you don't normally get that. How do you follow that up for an encore? What is the right way to go? Well, you know, Masai did an amazing job when you look at the big picture and I think that's, you know, he'll be celebrated, you know, when you look at what happened with the Toronto Blue Jays and their top executives winning a title in 92 and 93 and how they've been celebrated, I think you'll see that down the road as well for Masai, deservedly so. If you've made a decision to make a change, then to stay status quo for one year and maybe

go from there, okay that's understandable and if you're going to bring someone in with a you know fresh eyes, fresh ideas and then an evaluation of the entire thing that's something that's interesting too but you know obviously at MLSC you no longer have Brian Shanahan, President Shanahan, excuse me, and Masai Ujiri, yet with the Blue Jays you have, you know, Mr. Shapiro who is still the president. So a lot is going to come down to the comfort level with how many peers you want in leadership and how many voices you want and who that voice is that's going to have

access to the new ownership group. It's no longer a three-headed monster where you're talking to Bell and Larry Tanenbaum and Mr. Rogers. Basically it's going to come down to that person answering directly to Mr. Rogers and Keith Pelly in terms of how they want to go about it. So I think a lot of it's going to come down to the comfort level of how they want to structure it and what the term is for all these people. Hey, Jack.

Yesterday was the 50th anniversary, if you can believe it, of LeBron's famous decision to take his talents to South Beach. And I was curious how you see the latter days of LeBron's career plan out, because he's got the one year remaining on his deal with the Lakers. You know, his agent recently released a statement talking about how he wants it to be clear

that LeBron's trying to compete for a championship as if the Lakers aren't. I'm wondering how do you see LeBron James's last act playing out? Do you think he's gonna end the run in LA? Does he have another move in the cards? Any any speculation kind of feeling about where this all-time great will finish his NBA career? Well, he's an all-time great. And you know, the interesting factor is, you know, you look at what the Kevin Durant track transaction was, and you look at LeBron, you know, both in the last year that contracts and what the value is, I think people, you know know obviously the folks in Houston felt like the rank could make a difference in pushing them forward is there a team out there right now that feels like if they add LeBron James he can get him over the hump now based upon watching him play even though what is he 40 years

old the guy is still one of the top 15 players on the planet. So I guess you have to decide whether, you know, you're all in and you think this guy can do it at 41, 42, because I think Houston making the deal they made from a signability perspective and they had no state income tax, I think they feel like KD has another year or two left to make them a contender for two to three years.

So I guess the question you have to have is, can LeBron James in those years beyond this year do it for you. And if not, I don't know if you're going to be able to give up. Lake is going to get that much for him. They'll get, they'll get a good amount, but will they get what they really want? Um, or do they just play it out and clear that cap space? But nonetheless, they're going to have cap issues regardless. So to me, I think it's a difficult pro sports is so different now,

particularly the MBA terms of, um, I think the action now happens in the February trade deadline more so than it does in the summer. And I think with the, uh, luxury tax, uh, the first apron, the second apron, our new TV deal, the landscape has changed dramatically from a standpoint of how you build teams. And quite frankly, your window's probably three years. And I look at Chet Holmgren getting that new deal in Oklahoma City, and obviously Shago Diz Alexander,

both guys well-earned, well-des well deserved and we'll see how Sam Presti continues to try to put that together and keep that together in a small market that's going to end up facing the first second apron pretty soon it's fascinating how all this is going to play out because it's a new landscape for everybody and a guy like LeBron James even though he's one of the all-time greats, the system has changed so much compared to what happened when we had the decision where you could have Dwayne Wade there and yet you're bringing Chris Bosch from Toronto

and LeBron James from Cleveland. Those days are over. Jack, thanks very much.... remember sign your scorecard always signed already in our now i've i've been holding off now i have to go to the nineteen poll is that okay yeah and by all means i think that escort is waiting for you well i just got off the court and now i'm now i'm going to become the club

champ after a struggle on the first 18. Thanks very much, Jack. Be well. All right, guys. Hey, Dave, thanks for the props there. If you could be my representative kind of deal for me, it'd be great. Yeah, I'd give you a discount commission on your current guy.

No problem, Jack. It's all good. Thank you, guys. Have a great night. You too. Thanks. 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 iHeartRadio app or wherever you get your podcasts.