OverDrive - Dreger on Larkin’s trade request, Toronto’s coaching search and Cassidy’s situation

Episode Date: June 4, 2026

TSN Hockey Insider Darren Dreger joined OverDrive to discuss Dylan Larkin requesting a trade from the Red Wings, the complexity of navigating a player’s trade request for management, Peter Laviolette and Patrick Roy’s potential fit as Maple Leafs head coach, the latest around University of Denver head coach David Carle and Former Vegas Golden Knights head coach Bruce Cassidy.

Catch everything soccer with Bell's game time bundle. Get 5 TV with TSN plus 5150 internet, all for $99 a month. Price guaranteed for two years with a two-year internet and TV term and auto pay credit. Visit bell.ca for more details and to check availability. Bell, connection is everything. On that note, our Hockey Insider, Darren Dregger, now joins us here on Overdrive. Dreg's, um, how's it going? Anything going on right now in the hockey world?

No, nothing at all. No, nothing good at all. No disgruntled stars you want out of their city? Well, yeah, I mean, you're referring to Dylan Larkin of the Detroit Red Wigs. And, you know, when you think of bombshells, that's as big a bomb shell as we're probably going to get leading into the off-season post-down-the-cup. So I think there's need for a little bit of an explanation here. This has been in the works for a while. I think that's pretty obviously.

You don't just wake up one morning as a top player. and go, okay, I've been here 11 years, whatever it is, hasn't worked out. Time for a fresh start. You mean like years in the making, Darren? No, years probably is a stretch-o-dog, but, again, you think of Dylan Larkin, I mean, you know, it feels like he was born and raised to play with the Detroit Redwins, you know, obviously, right? Like, that's where he's from.

So for Dylan to get to the place where he's, you know, he's. requested a trade, that tells you that there's been a lot of thought, and there's layering to all of this. I mean, the man has a family, and I don't think it's as cut and dried as him, you know, wanting an opportunity to win, and he doesn't see that opportunity in Detroit. I think that's maybe where it starts, but then there are multiple layers that go beyond that. How did he get to this point? You know, did management do enough to insulate him to augment what they have, all of those things. And, you know, those are questions that I suppose Dylan is going to have to face if or when a trade actually happens. But the information is legit. And I think that he and his representation were to

CAA, it's Pat Rieson and J.P. Berry in that group, are dismayed that the information got out in the fashion that it did. Because when you're talking about a top end guy like this, especially in a market like that where, let's be honest, there aren't that many stars that play with the Detroit Red Wings. They're good players, but Dylan Larkin is kind of the one guy that stirred the drink. We saw that when he got hurt this year. So I think they wanted to do their business beneath the public eye and underneath the surface, and it just hasn't worked out that way. So, man, talk about a laundry list of teams that are going to be interested in this fellow. You know, he can flat out play, so we'll see how it all plays out.

Darren, can you explain the complexity of a player that wants out and also has a no movement clause? Like how that works, just with, you know, where he wants to go, can go, where the team wants it. How does that all come together? It is complex. So, you know, your description is accurate. And again, I think that's why maybe the player and his representatives would have preferred and not get out publicly. because that way, oh, you can do your work confidentially. You can go to management.

It's not the first time this has happened. Say, look, it's time for a change. And so we're formally requesting trade. Here's the list of teams that we're interested in going to. So have at it. And that can get a little spicy too, right? I mean, the team doesn't have to automatically say, all right, well, we respect your trade request here.

So we're going to do everything within our power to move you to, you know, Minnesota seems to be the flavor of the afternoon based on social media speculation. And we can appreciate that Billy Aaron would have a ton of interest in Dylan Larkin, you know, it's great captain and all of those things. It does get a lot more complicated when it is now as public as it is. Because Steve Eisenman might be next to Lou Amarillo when he was the general manager, The most private GM there is in the National Hockey League. Nice man.

See him in the hallways. The fancy hotels we stay out when there are general managers meetings, but he does not pull the curtain back. He does not. So this whole process is going to anger him and it's going to get complicated. So, Dregs, we were talking about before you came on, the process of how this would go down. And I kind of, you know, I may have spoke out of terms,

but do you feel sometimes if the information gets leaked out, either to the insiders or to media, all of that type of stuff, is that sometimes the way of testing the marketplace? And, you know, I know agents would be pissed, all of that type of stuff, but you know how this information, it's almost like a trial balloon is like, okay, let's get the marketplace going here a little bit early on. Sure. Or would it be behind the scenes that every manager would know that he's available? already?

Maybe some would have known, I can tell you by the GM reaction to me, based on the news breaking this afternoon, they didn't know. And these would be managers who are in the market for that type of player, like a centerman, right? Now, you know, Dylan Larkin's going to have a big say in what that market looks like. We've already established that. yeah I honestly I'm not going to waste any time digging on and on digging in on how the leak happened but as we've just talked about here do we honestly think that that information is coming out of the

Detroit Red Wings organization yeah I don't like I don't think so I don't know anybody inside that organization starting at the top with Steve Eisenman that wants that out there because he wants to either apply public pressure to larkin or to see what the market it actually is. And based in the reaction that I got from the Larkin camp, they don't seem too happy that the information is out there either. So there's a myriad of

ways that this stuff gets reported. It happens on a daily basis. It just isn't as surprising as this one is, just based on the status of the player with the Red Wings organization. All right, so something to keep our eye on, something that we're

all sort of monitoring day by day and you came out with the report yesterday that the Maple Leafs have interviewed Peter LaViolette and Patrick Waugh for their head coaching candidacy or vacancy right now. Patrick Waugh, obviously, there's a reaction there given his history as a player, his history as a coach, his connection with the Montreal, Canadians. What you know from this new management with the Maple Leafs, do you see him kind of aligned with their vision of where to take this Leafs organization?

It's a great question, Mark. I don't think anybody really knows what the direction is, to be honest. And, I mean, by anyone, outside of John Chica and Matt Sundeen and, you know, the group that's intimately involved in this hiring process. You know, as Chica said when they fired Craig Barubei, you know, his media availability, the web was going to be wide, right? Like, they were going to kick all sorts of stones and look at it. every corner and make sure that they interviewed everybody.

Okay, so why wouldn't you, you know, have a conversation with Peter Laveolette, given his experience as a Stanley Cup champion, I would be intrigued by Patrick Watt. I mean, he wasn't the fit for the New York Islanders as they moved forward. They thought it was better that they go with Pete DeBore, who's got more experience in that sense. But, you know, Patrick was an intriguing guy. He certainly would get the juices flowing inside the division, but we're looking at a couple of guys who are involved in a bigger process. And what I was reminded of earlier today by somebody who was involved

is that they still don't have a timeline. You know, like Chica and company, they're invested in what's going on this week at the draft combine in Buffalo, and then the draft isn't that far down the path. So even to establish when they want to have a head coach in place, they don't have a timeline for that. So that tells you that they're going through whatever their process is, as extensive as it is. And even, you know, like the follow-up interview with Patrick Gua, with respect to everything that has gone on in the hockey world,

I think Patrick Waugh told him, look, of course I'm interested in a second interview here, and that's likely going to be face-to-face. But he wants to get through all the Claude Lemieux funeral arrangements and everything that's gone on to saying goodbye to a good friend. And so there are lots of things that are factoring into this. So, Greg, David Carl, has he only said no to the Maple Leafs or has he said no to the NHL altogether? Yeah, I think O to the NHL altogether, to be fair.

And I don't know that it's a hard no. You know, David is, he's a bit elusive. You know, he's not campaigning. He is listening. He is evaluating, but he doesn't have an agent. He's not campaigning to jump into the national hockey. What we know he's doing is what has been announced and reported on the last couple of days. And that's looking after player personnel with the Denver pioneers.

That's where his focus is, right? So it sure doesn't seem like it's likely that he's going to make that NHL move this year. but based on last couple of years, not just this year, the interest around David Carl, I think he's confident in his own coaching ability and future that he believes that the opportunity is going to be there when he and his family are ready. And the opportunity, whether it's in a market that he approves of, closer to wherever he wants to call home financially, all of that, it's going to be there. It just doesn't seem like it's going to be there.

be this year. Drag, so I want to ask you about the Edmonton Orlers, because I find it fascinating that the information got out, however got out, that they wanted to interview Bruce Cassidy and they were denied by the Vegas Golden Knights. And now I haven't heard anything

about anyone else, maybe that they're interested in, and maybe I'm just not, you know, I'm not close enough to the situation, but is this a situation where they're still hopeful that they eventually will get permission to interview Cassidy, or are they keeping things a little closer to the best? Well, both.

I mean, I think they're absolutely hopeful that they'll get permission to get to Bruce Gassity. A bit of a risk, I would say. I haven't heard of who their plan B is. I believe that Peter Lavial has been to do that process. I know that the Los Angeles Kings continue to do their due diligence on Lavie. We know that Stan Bowman and Jeff Jackson spent time with Craig Barubei a couple of weeks ago in Toronto as part of their interview process. but I think it's relatively quiet on that front. So you start to wonder a little bit because, you know,

the commissioner's availability with Deputy Commissioner Bill Daley, you know, Daley basically said pre to game one in the Stanley Cup final that they were comfortable with the position of the Vegas Golden Knights through the playoffs. But that kind of offered a hint that maybe the NHL gets back involved, they can legally, I don't know that they can, if they can, after the Stanley Cup is awarded. I mean, if you're in Vegas, you've taken this position at this point because you're trying to block two division rivals in Edmonton and L.A., why would you relent?

Why would you back off after the Stanley Cup has been awarded? You know, if you don't want to coach against Bruce Cassidy in Edmonton or L.A., you have them under contract for another year. So, you know, unless the NHL is back-channeled and given the Oilers and potentially the L.A. King's more information than we have, then I think it's a risky game that the Oilers are playing. I do believe that Edmonton, whatever direction they're going, whether it's Lavie or it's Jay Woodcroft or somebody else, it does seem like L.A. is closer to naming a head coach, perhaps as early as midweek or, late of next week. So that tells me that the LA Kings aren't going to wait around for Bruce Cassidy. Just quick on the Cassidy situation.

You know, we know how Vegas does business. They play for keeps, all of that type of stuff. But, you know, would that affect any type of potential coach that they ever wanted in the future? It goes, hey, you fire me and you're going to make me sit on the sidelines like we did. We saw with Butch. Yeah. Yeah. In my noodles. So I guess what I'd like to know more about, and this kind of stuff we don't know about, is how does one coach contract vary from another coach contract? And will there be a standardized coaching contract at some point moving forward? We know there's a coach association, and I think it's a healthy thing for NHL coaches. But if you don't have a standardized contract, that is the same in one market as compared to the next as compared to the, next and the NHL isn't going to get involved to manage that sort of process, then what are you left

with, right? I mean, if Bruce Cassidy had a way to get out of his contract, but he said it. He said it publicly. If he could resign and forfeit the four and a half plus million dollars, whatever it is in the remainder of his contract, he would do that. Well, what else is left for him to do? Nothing. You know, he's contractually bound. So I, I mean, it depends on the coach we're talking about here. Do you want to go to a place where you think you can coach a team to the Stanley Cup final? And you're getting four plus million dollars on a multiple-year deal to do that? I think I'd be willing to sign up.

And, you know, the consequence is that in the final year of my deal, I get gasped because my team isn't responding, but I'm still getting four and a half. I may not like that they're blocking my path from coaching the team I want to coach, but I'm still getting paid and contractually I'm obligated to stand the ground. So I'm not so sure it's going to impact Vegas negatively moving forward. Gregs, you just mentioned Betman. How long do you think he talked about a succession plan, succession plan? How long do you think Uncle Jerry is going to stick around for?

I mean, I chuckle, not because of the question. No, I chuckled for a couple of reasons. Uncle Jerry makes me giggle every time they hear it. But there was an incident, and I use that term appropriately, this going back a few years ago at a Board of Governors' meetings, where Pierre LeBron felt like he had a big scoop, and that Jerry, Gary Batman was a slip right there. He was about to present.

his owners that succession plan. Like, here's what we're going to do. It's going to be my, my suggestion is Bill Daly, blah, blah, blah, blah, whatever it was. And so, Pierre, I mean, he's a pro. He talked to Bettman multiple times over the course of that two, three day meeting span, to a point where Bettman was getting sour with him. He was getting surly. And he was like, do not report this.

Do not say this. You will make yourself look foolish. But, I mean, let's be honest. You know, given everything that Commissioner Brettman has done, the billions of dollars that he's brought to the league and to the owners, the age he's at, you know, he's got, you know, a flock of grandchildren, all of those things, you know, and big business, corporations do this all the time. You have to have, you know, a corporate succession plan in place. So, I don't know. What does he have? A year or two, three years left.

I'm not going to be the guy that pinpointed that, because he's going to be in that office for as long as he wants. wants to be. All right. Well, next time we have Pierre on, we'll have to ask him about that story. Yeah. Anyways, lots to talk about it this time of the year, Dregs. We appreciate you coming on. Gay, fellas, have a good night.

There we have it. Our hockey insider, Darren Drager. Hello, Canada. This is Brian Adams Radio. Hosted by Brian Adams himself. We'll play a few of mine, a ton of my favorites, and some must-hear behind-the-scenes stories from the world of rock and roll. One thing about doing rock and roll so long is you end up meeting a lot of the people that you admire.

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