OverDrive - OverDrive - August 18, 2025 - Hour 1

Episode Date: August 18, 2025

Join Michael DiStefano and Dave Feschuk for Hour 1 on OverDrive! The guys discuss the Blue Jays' series victory against the Rangers, the Blue Jays' pitching rotation structure, Jose Berrios' tough outing and his stance in the lineup and the matchup against Paul Skenes and the Pirates. TSN Raptors Reporter Josh Lewenberg joins to dive into Bobby Webster leading the Raptors becoming the head of basketball operations in Toronto.

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apply. This hour of Overdrive is powered by Fanduil. Fan Duel, bringing you everything from the opening line to the final score. Off and running here on Overdrive coming off a busy weekend. It's Mike DeStefano. Filling in for Brian Hayes. Got Dave Festchuk of the Toronto Star. In with me here till 7 o'clock. And boy, what a weekend we had, Dave. I was down at the Jay's Game Friday. Nice. Which might have been one of the best games to attend this season. I got to witness something. that I didn't think I would ever, ever see in my life. Alejandro Kirk stole a base. Yes.

And it's Monday, but we're still buzzing about that base deal on Friday. We are. Like, what a visual. It's one of those, I don't know if I'm being hyperbolic here, Dave, but it's one of those, I remember where I was when type of moments for myself. Well, when I watched that AB, I'll tell you what I thought of, it was shades of you and the O Dog running the 40. Wasn't it?

It's funny because I was having a conversation with producer Owen, who was doing the gameplay beforehand. And I was like, oh, I wish I thought of it. But imagine if we were able to get like a side by side of me running my 40 and then Alejandro Kirk stealing the base, which seemed very effortless for him. I mean, the guy doesn't attempt to steal bases. I don't think you're expecting Alejandro Kirk to take off from first base.

but he did, he caught him slipping. And so being in the stadium was funny, though, because, you know, people saw him steal the base and it was hilarious. You kind of laugh. It's like, oh, Alahado Kirk did it. And then it showed up on the Jumbotron that it was his first career stolen base. Yes. And the place erupted.

It was hilarious. People bowing down like, holy smokes, we witnessed history in the making. It was awesome. That was the beauty of it. It was like, you watched it, and you were like, did I just see? what I thought I saw. Look at this guy. Look at this guy.

Didn't even need to slide. No. Didn't even need to slide. Stand up. Yes, nice gesture there by Vladdy. Yeah, Vladdy, given the base to Alejandro Kirk after the game there. Yeah, like shades of Ricky Henderson breaking the all-time record giving him the base. I love it.

Yeah. But you're right. It was like, you saw it happen and you're like, okay, that's unusual. And then you didn't realize, at least I did. I did not realize that he'd never done that before in his entire base. Paul Carrere. Yeah, it was a great ball game, though. And, like, he was the center of it, right? Like, he gets the stolen base. He had the home run to

kind of get the offense started earlier in the game. And then with the base is loaded, you know, rips a single into the outfield, brings in the tying and game winning runs. And it was the Al Kirkch show. It was the Kirky show that night. And it was a great win, transitioned it.

Are they, you know, 14 to 2, an absolute drubbing on Saturday. We're at with the pitchers, position players pitching in games like that. Are you for or against? It seems to be a very split community on this. I mean, I'm for it. I mean, how are you going to stop it?

First of all, like, what rule would you put in to stop it? Well, I think you would just have to have a designated pitcher must pitch. Like, that's the rule that you would have. I mean, I don't think is that difficult to outlaw if Major League Baseball really wanted to. You could, except that, you know, there'd be complaints about that. You're already complaining with the fact that pitchers are, you know, losing arms at, you know, unprecedented rates. You get injured.

You essentially got an injury epidemic in the pitching community. And now you're going to say, no, no, you have to pitch no matter what. It's difficult to imagine how you're going to outlaw that without a major uproar. And then people pointing to the idea that, hey, you're putting more workload on these. This is work they don't need. And so the idea, and it's a long tradition of, you know, catchers coming in and outfielders coming in and throwing up fat pitches in a blowout game. Do you find it entertaining, I guess, is ultimately like sports supposed to be entertaining. I find it a little cringe and embarrassing.

Like, I think that's where I'm coming from. And Rowdy Tellez, former Blue Jace, was kind of funny. I wonder if there was, like, that whole aspect of why he was in there to pitch in that blow at loss. But he goes out there, pitches two winnings, gives up a couple home runs, hits a batter. Like, it's a little embarrassing. It's like, this is Major League Baseball. Like, how is it that we get to a point where Rowdy Telez is out there pitching against Major League Talents? Hey, well, first of all, it's not exactly the Zamboni drive.

coming in to play goal. Well, it's not, but it is. Like, pitching is very hard. Yeah, but pitching is very hard. It's not as, like, first base of pitching is not the same at all. I know what you're saying, look, yeah, most, let's face it, anybody that makes the major leagues has generally been a pitcher at some point in their baseball career, usually in youth baseball.

If they're not, you know, or maybe high school baseball or perhaps college baseball. So these guys know how to throw a baseball pretty damn well. I mean, it's similar to the Zamboni driver. They know how to get into a butterfly. and flash a leather. No, it's not similar to Zamboni driver because the Zamboni driver is not a professional athlete. These guys are professional athletes.

Look, I understand, but how do you really you say it's cringy, you say it's embarrassing? I agree, it is, but how do you sort of make a blowout not embarrassing and not cringy? Like, does it really make it better if there's only professional pitchers pitching? I mean, I'm not sure.

I think there's a certain curiosity to the idea that, you know, a position player can come in and actually hold his own, which often does happen. Sometimes you do see it, like, like Heinemann went in for the Blue Jays in the ninth inning to close out the ball game, gave up one run, but it's like, all right, he got it, you got through it, he got it over and done with, but it's, it would, I'm not sure basically baseball cares enough to, to switch that out, and I get it, you know, a game that doesn't matter.

Do you really want to hurt the arms and put more stress on arms? Like, I understand that argument, but it's just, it drags it on. It's like, you got rowdy out there for 30 minutes tossing meatballs, getting cranked into the second deck. It's like, I'm done with this game. That is the problem. I agree with you. But there's no one, like, I'm not sure there's a way around that. I'm really not. It could because, you know,

sometimes you just get blown out and sometimes guess what? The pain hangs around longer than you'd like it to. And so I get where you're coming from, but, you know, I just, I think it's just going, I just think status quo is probably going to prevail there. I don't see a movement to change it.

Yeah, probably not, but I don't know, Steve Phillips can join us at 505. We'll see what Steve thinks, potentially. Paul Skeens in action tonight taking on the Blue Jays. I saw a ridiculous stat about Paul Skeens. He has not allowed a single run at PNC Park since June 3rd, not July 3rd, since June 3rd, Dave. Like, that's two and a half months that this guy is pitched in his home ballpark. It hasn't surrendered an earned run.

So the Jays will have their handsful tonight. But they've done well against good pitching. Yeah. Like they've done fairly well against good pitching. Even that game Friday night, like it was Jacob to Grom. And it's not that they have to get the runs off of the starter. But if they could put together quality at bats, like they got to Grom out of the game in the fifth inning that night. And then they got to the bullpen.

If they can somehow get schemes, you know, get them out of the game after five, six innings, then work on the bullpen, which they traded half their bullpen away at the deadline. They got a bunch of, you know, AAA relievers out there. That's where I think you can really start to see the Blue Jays do some damage tonight. Well, look, I mean, Paul Skeins is a phenom. There's no doubt about it. But he's showing some signs, maybe not at home, but he's showing some signs of a little bit of fatigue.

Maybe he's a little worn out because two of his most recent three starts, obviously these two of these two coming away, because as you pointed out, he hasn't given up much. Two of his most recent three starts, he's giving up four runs in each of them. So, and he hasn't, what, he made it to four innings in one of them, in five innings in another. He's throwing three shutouts in the other three.

No, I know. I'm just saying, like, he's shot at him. shown at least some signs of being human, right? And the fact that the fact that this guy has, you know, an incredible, an incredible ERA of 2.13 and a win-loss record of 7 and 9 tells you everything you need to know about how bad the pirates really are. Well, I wonder how much, like, a guy like that could lose motivation down the stretch, right? Like you talk about it may, maybe it's fatigue potentially, but also like mental fatigue of

going out there, being the best pitcher in baseball, but having it ultimately go nowhere. Because the team continues to lose games that you're out there pitching your ass off. But, you know, he's the frontrunner for the Sion, somehow, a sub-500 record. Yet he is the betting favorite on Fandu right now doing the Siling. I think it's like minus 425. I was looking earlier today. It's like strong, heavy favorite. And he's a 7-9 pitcher.

Well, basically every metric he can look at tells he he's the most dominant pitcher in the game. I mean, I don't think there's a lot of debate about that. Or if he's not the most dominant, he is among a handful of the most dominant. dominant. And this year he's been the most dominant. So, yeah, it's, it's, it is, like, you have to wonder, like, what goes through your mind. When you're that good a competitor, like this guy is a ruthless gamer, right? Like, you go back to his college career and you hear the stories about, about his intensity and his ability to bring it when it matters. When you know, no matter what you do, it doesn't matter in terms of winning games for the

Pittsburgh Pirates, because they're just not going to win games. No, no matter how good you are. They're not going to win enough of them for you to matter as a competitive player. And you start going down the road of, you know, is this the next Mike Trout? Is this the next sad, sad story in baseball? I suspect it's not going to be because you believe the pirates will cash out on Paul Skeen's at some point, right? But you can't come soon enough. No, it can't. It really can't.

He's a player that you need to have in one of those big, big markets. And whether it's the Yankees, the Red Sox. A lot of people in Toronto don't want to have to face him, you know, eight times a year or face the, well, probably like two or three times a year, I guess, as a starter. But it would be great for baseball as a sport to see him in one of these big-time markets, right? Maybe some to the Dodgers where the Toronto would only have to play him once a week. The Dodgers get everyone anyways. You might as well load up on star talent.

Speaking of, though, there was, I think we have the clip here, Bob Manfred, and he was talking about realignment, possibly, and some expansion talks creeping into Major League Baseball, which could kind of shift things around. Why don't we hear that now from old Bobby Manns? Okay. We'll try to get that in a little bit. But it is interesting.

It sounds like MLV, Major League Baseball, considering some expansion, try to grab a couple other teams, to bring it to every other team or every league is doing. doing it. It's the biggest way to add revenue to your sport and, you know, there are figures being thrown out that an expansion team could cost upwards of two billion dollars to bring in a franchise. But if you do that, then there's the conversation of, okay, well, now it's, if you bring in two franchises, you're at 32 teams, this is your chance to maybe do some

realignment. And that's where things get real interesting in baseball, because if you decide to realign, do you do it in terms of proximity, of, of location? where you are, or do you keep, you know, the lower of the American League in the National League alive? It is a fascinating question that if they decide to go down that route, what they would like to do? Like, do you have a preference on what they should do if you were asked? Well, look, I mean, you know, you start, when you start hearing the comments from Bob Manfred talking about, I guess it's Rob, right? We should probably call him Rob. You're calling him Bobby. Is it Bobby for you? He's Bobby Man's on this show all the time.

That's what's hazy people. and the O-Dog, well, Bobby Man's. Bobby Mans. Yes, okay. Robert Manfred would be his given name, I believe. Robbie Freds? I don't know. Like, which one is it? No, I'm with you. But, I mean, he's talking about geographical realignment,

and there was a mention of saving on travel, right? Of course, there's always cost savings involved in these things, right? So, look, I think if the American League and National League have been serving you well all these years, like, I don't know why you've got to go to Eastern Conference, Western Conference and be like the NHL and the NBA. Well, I mean, the one thing I would push back on is

the National League and American League used to have one big difference, right? And the National League pitchers used to hit. Yeah. When they got rid of that, it almost takes away the love or the difference of what the National League and American League are. And it's almost like it is the same. So why not have

proximity kind of come into place? That's where they've been heading, right? Right. I mean, that's where they've been headed. I mean, I guess, you know, The NFL hasn't done that. They've got the AFC and the NFC. And those are historical lines that have been drawn that speak to where the league came from and where it originated from

and how football evolved over time, right? Although those things get played with as you move forward. But yeah, I mean, you know, so if I'm betting on the way it's going to your point, yeah, it's been heading this way for a long time ever since they took out the major delineation in the rule book that, separated the National League from the American League.

It seems like it's heading toward East and West. And it seems like to me, like it could really benefit the Blue Jays. Well, you get them out of the American League East. You don't have to play the Yankees and the Red Sox, you know, or the Rays who always give them fits, you know, 18 times a year, or whatever, 13 times a year than that play them. Like, if you're talking about, if you're talking about,

I mean, not that we know how it's going to go. Like, does it make sense that the Atlantic Division in the NHL includes the Leafs? and then these Florida teams? Yeah. Why are the Leafs in a division with two Florida teams? I don't know. Right. Like the Rangers are much closer than Detroit's down the road.

They're not in the same division. You know, like, so that does, Buffalo's down the road. They're in the division. But I'm saying like, why is Detroit not in and Buffalo is in? Why are the Florida teams, you know, included in that and not, you know, lumped in with the New York teams further, which are a lot closer or at least a little bit closer. Who knows why they're going to do these things? But, I mean, you know, you look at some of the pie in the sky speculation,

the idea that you would have a Great Lakes region kind of team where it's like Toronto, Cleveland, Detroit. Yeah, now you're talking, right? Yeah, Cincinnati, I think, was throwing. Cincinnati you could throw in there. Yeah, I saw a propose, like, what they could look like, and that was a team. Pittsburgh's not that far away. Just a little bit down the road from Cleveland, you know, a little south.

So, I mean, there's, there are scenarios you can sketch out where the geographically close teams for the blue. are essentially financial weaklings. And that would be a very good development if you're Mark Shapiro and Ross Atkins and the Rogers Corporation. It would be. It certainly would be. So we'll get Steve Phillips thoughts on that as well. Join us at 505. Farhand Lodgey at 5.30.

Get his thoughts on another busy weekend in the CFL preseason week two in the books around the NFL. Ross Tucker, good joins at 605. And Lawrence Alpabobam at 630. You're going to join us as well. Get into some golf action. What a shot by Scott. Sheffler. One of the best shots I've ever seen. That is

going to end up in a montage someday when they put out the 30 for 30 about Scotty Sheffler and that might be the one where it's like best shot he's ever had. Yeah. I mean and of course. He's got a lot of them. Scotty being Scotty he's like just a straightforward chip. That's where I wanted to

Oh yeah, 801, 81 foot chip that just rolls forever and ever and ever and just drops in unbelievable. This guy is just so, so good. So Lawrence Appleman, I'm going to join us at 630 to get into that. A couple Canadians advancing to the Tour Championship, so that's exciting in Cory Connors and Nick Taylor. But I think the big news here in Toronto today is the Raptors have appointed Bobby Webster,

the team's head of basketball operations, not the president. He's not getting the president's role, but he's being appointed as head of basketball operations. you're very, you know, intertwined with the ongoings and what happens here in the city of Toronto and management. Like, what did you make of that when you heard about this this morning? I mean, what do you know? Like, who could have seen this coming? I'll tell you what, on the day Masayu Jiri was fired

and it was announced that they're hiring this global CIA executive search firm to go search high and low for the next Messiah Jiri, for the next Raptish president. I don't think there was anybody tightly involved with this that thought they would end up saying, oh, let's just give it to the guy that's sitting next to Maasai, you know? And by the way, let's not, let's go searching for a president, but let's not name a president. You're not president, Bobby, your head.

Yeah. You're not executive VP, your head. Like, what are you? How is head for a title? I have no idea what this means. Like, obviously he's going to have more control, I suppose, of what goes on. But now I question, like, well, how much control did he have then? at the start.

And there's always been a little bit of, you know, convolution when it comes to how much of this team, how much fingerprints was Maasai compared to, you know, how much say to Bobby Webster have as a team's GM. And I guess that is one thing that we probably will find out moving forward, you know, the difference of, all right, well, what was Maasai and then what was Bobby based on how the differences go and how this team is operated over the course the next few months, I'd imagine.

Look, I mean, there's no mistaking who was. in charge of everything in Raptorland since 2013 when Messiah Jiri arrived here. And it's been Messiah Jiri's team from the day he got here, right? Well, I get, but then, like, Keith Belly comes out today, and there are comments. Like, you know, it made all the sense in the world to give Bobby a chance to see his plan develop. Well, whose plan will? I thought, like, it was Maasai's plan. So if that's the case, like, is he moving on with Maasai's plan?

Is it his own plan? Are we going in a different direction here with the Rappi? I'm kind of confused to where we're going here. No, I see why you would be. I mean, the whole thing's confusing. I mean, it doesn't make a ton of sense because everybody else was under the impression

they were going to look for a new president and name a new president. And now they have not done that. And they're saying, yeah, we may name a new president in the future, but not today, not right now. For now, we are going to be in a holding pattern with the guy who was besides number two as the new number one.

But we're not giving him the president's title and presumably we're not giving them the kind of money we would need to give them to be president. Well, that's the other conversation, too. It is like how much of this is a fiscal decision, you think? Well, Messiah, Jerry was making a lot of money, and I can tell you right now that

Bobby Webster. He's still making a lot of money. Yes, he's being paid for next season until the end of next season. I'm not sure exactly the arrangement of how he'll get that money, but he will get it. Yeah. And knowing Maasai. So, bottom line is, yeah. Like, you know, it's a new era to

with an old face. And it's not unlike the massive search Al's brother that they held to find Dwayne Casey's successor. They hunted high and low. They interviewed a cast of many to see who would replace

Dwayne Casey as Raptor's head coach. Mike Boodenholzer was in there. Tori Messina, the great European assistant down in San Antonio. I can't remember all the names that they were on the list of people who interviewed and were considered to replace the way and Casey and then you know what they did they

but the guy who sat next to him for years the guy that sat next to him for years so it's exactly the same thing essentially but to your point about the plan like look Bobby Webster was involved in this interview process run by this search firm that I'm sure Mipley Sports Entertainment paid a very good buck to run this search for them

and everybody involved in those types of searches knowing what we know from past experience and from, you know, anecdotal observations from this experience from people who've been involved in it, I mean, you present a plan. Like you have to bring your PowerPoint to the interview, and you say this is how I see this team. This is what I think of the roster now.

This is what I would do with it tomorrow. If I was named president, this is how I think we can get better. This is how I think we're limited in ways we can get better. This is what we need to succeed. This is what I don't think we need. This is where Maasai got it right. this is where Messiah got it wrong. Bobby Webster is no different.

Like, you know, Dwayne Casey was in on this. He had to do that. Kevin Pritchard of the A. The A.A. Paces was in on this. Everybody was involved in this had to present a vision for the Raptors to Keith Pelly. And I'm sure Bobby had a very clear vision of what he saw. And now Keith Pelley has bought into it and said, we'll give you a chance. Well, it's a new era in Raptorland, I guess.

Maybe. Kind of same like the old era. Possibly. But, hey, when they made that change from Duane Casey, right? They did win a championship with Nick Nurse when they made that swap. And with Kauai Leonard. A little addition named Kauai Leonard. You're saying Brandon Ingram doesn't provide the same gravitas as Kauai Lenners.

Is that what you're telling me, Dave? That's exactly what I tend to agree. I think it has a chance to be good if he ever plays. Yeah, well, that's fair. Well, Josh Lundberg, our TSM Raptors reporter. He'll join us next. We'll get back into this story and get his thoughts on what went down today in Raptorland. I'm Mike DeStefano and Dave Festchuk.

We're on TSN2, the TSN App and live up on YouTube. Overdraft continues on TSN-1050, live on TSN2, live on YouTube. Mike DeStefno, filling in for Brian Hayes, the captain, Hasey B. We'll be back next week. And I've got Dave Fesshuck of the Toronto Star with me. Some breaking news earlier today. The Toronto Raptors decided to name Bobby Webster, the head of basketball operations. Not the president, just the head of basketball.

operations. What exactly does that mean our next guest will tell us? It's Josh Loonberg, our TSN Raptors reporter. What's going on, Josh? Not much. How are you guys doing? We're doing well, 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 Maasai 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 and 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 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 Kim Lai Wiki, 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 Presti 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. 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 mean, 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 MLSE three times. times last month. If they weren't enamored with any of the guys they could get with what I understand

is a pretty modest budget, then this allows them to continue grooming Bobby and Dan Tolzman and see how it looks. 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 there was, you know, 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, you know, every expectation and was a very different coach than Dwayne Casey,

even though he'd been sitting next to Dwayne 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, jury? 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, 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, like, I think Bobby's vision from a basketball standpoint

is probably pretty similar to Maasai. 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 Maasai 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? 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

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 in that the Messiah firing had 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 controlled 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 Maasai 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 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, well, 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 Ujuri 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 core, 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 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, like, 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 Webber, or 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 Messiah Jiri salary. And that's maybe why they weren't able to attract more interest and more, um, bigger names in their search for this position. If they

weren't willing to pay top dollar, then yeah, I mean, I, I heard the name Kevin Pritchard, the Indiana president as somebody that they were interested in. But if, 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? 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, 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 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 operation, and when we're talking about the disappearance of these presidents and a lot of other things that are happening around Maple Leaf 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.

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 a couple, 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. do. 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 being 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 before opening night. But if you told me that R.J. Barrett was moved at the trade deadline or even somebody like O'Chai Abaj 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. And 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 Lumberg, our TSN Raptors reporter.

Yeah, I mean, like, the problem is, like, it's, it's an average basketball team. Like, that's the issue. Like, they're good enough to maybe make a run and make the playoffs, more likely to play in team. But they're over the apron. Like, it's just, it's a weird team. To roll and continue with that same plan, that same vision is just a little perplexing to me. If you didn't like what was going on before, like, what are we doing here? Well, in some ways, A, B, I agree with you that, you know, they're not on a great track right now.

They're paying a lot of money for a lot of guys who've done very little to prove to you that they can be the heart of a championship level team. And you've got championship level expenses on your payroll, right? Like, this is a very high payroll team. You know, the manual quickly contract has been sort of dragged around the NBA this summer as a real bad precedent that other restrictive free agents are pointing to as, That's the contract I want that. And teams are saying, no, we're not giving you that. Only the Raptors don't give somebody that deal, given Emmanuel Quickly's resume. And the Ingram contract has not been treated particularly kindly when, you know,

Ingram's own agent has gone on the record saying, I couldn't have got that $40 million a year anywhere else other than in Raptor land. Not a good look for the Raptors, right? And I understand these things happen and the Raptors are in a unique position as the only team above the 49th parallel and the only team of the United States. but bottom line is they're not in a great spot and to be the kind of team they hope they can be and it's going to take some tweaking more than tweaking it's going to take some reimagining of how you move some of that money out

and move better money in and now it's on Bobby Webster in what looks like a pretty short window here because there was no mention of a multi-year extension in the press release we don't know the exact terms here but if it was a multi-year deal they would have said it was a multi-year deal it seems like he's got a pretty short timeline

here to say, I have a vision that will get us a place we haven't been in a while. And Keith Pelley's basically said, yeah, go prove that to me and then we'll talk about the presidency. Yeah, I do find it interesting too how, like Josh was saying that, oh, a fair amount of people who interviewed for that presidency

role came in and said they didn't like what was going on with the Raptors, not a fan of a couple of trades and extensions, the Ingram situation. And meanwhile, they decided, well, we like it, and we're going to continue with that. And here we are. We'll see. best of luck to Bobby Webster's great guy you know he comes on the show all the time he's been around

he's technically won a championship as a general manager of the Toronto Raptors so we'll see what he can do with a with a bit more responsibilities and who knows maybe just like we were surprised by Nick Nurse perhaps Bobby can surprise us and you know move forward and get this vision going as well so yeah we'll see what happens there Steve Phillips still to join the show at 505 far on Lollgy at 530 and Lawrence Applebaum can join us at 630 as well. I'm Mike DeSepano with Dave Festchuk. You're listening to Overdrive on

TSN 1050, live on TSN2 and live on YouTube. Overdrive continues on TSN 1050, live on TSN2 and on YouTube. Mike DeStefano here, Dave Festhuk of the Toronto Star and all summer long have been

doing these brackets here on TSN 1050. And this week we got a brand a new bracket that we are unveiling now you can go and make go vote on the TSN 1050 Twitter account. We're looking at the worst Toronto

sports trades. Just off the top of your head can you think of a couple, Dave. I'll let you know where they are on our bracket here. I mean, I always think about because this is overdrive because the legacy of John Ferguson Jr. is

never far from the top of the mind. I can neither confirm or deny that. Thank you, J.P. Because of that, I always feel, I always think about that that little goaltender named Tuka Rask that was drafted by the Leafs, but never played for the Leafs. Yeah, that's the number one seed. Yeah. That's the number one seed here on this one.

I would imagine that that is a good, that has a really good chance to win. It's matched up against Soroka to the Jays, that trade that didn't turn out too well. The Tyler Biggs trade. You remember the Tyler Biggs? It's not necessarily, it was a trade of draft picks. But the draft picks at the least gave up to move up to take Tyler Biggs turned into Ricard Raquel and John Gibson. That's right. Two players that the Maple Leaf certainly could have used over the course of the last, what, 12 years ago that draft was.

Maybe it was like 15 years. That's like 15 years ago, that draft now. Yeah. And the worst part about that was that, you know, they got Tyler Biggs. And that was during the Brian Burke era where they were like, we're not drafting anybody under 6-2, man. None of these small guys are going to play for us. There were some good players, too, that went right after that. Yeah, and then they said, oh, yeah, you knew the red flag, Al's brother,

when they said, he's not a goal score, but we're going to try and turn him into one. Because when does that ever work, right? It's never positive, though, when, you know, Bob McKenzie hops on the broadcast, and you're like, player comparison, like, yeah, it projects to be a fourth-line center. It's like, your first-round pick is a projected fourth-line center. And he never turned into that. And he didn't even turn into that, sadly. Yeah, that was a pretty bad one.

Cadry to the avalanche for Tyson Barry. That's on here. The Kessel deal is on here. Vince Carter to the Nets, New Jersey Nets at the time. That was a bad trade, but... That was a tough one. Blame Vince.

Blame Vince. All right. That'll do it for hour one. Hour two, coming up next. You've been listening to Overdrive, powered by Fanduel. Fan Duel, bringing you everything from the opening line to the final score. The biggest songs in the world.

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