OverDrive - Dreger on the Maple Leafs' GM search, managing in the market and Gillis' potential role

Episode Date: April 21, 2026

TSN Hockey Insider Darren Dreger joined OverDrive to discuss the Maple Leafs' general manager search, the potential candidates for the hockey operations, the managing viewpoint in a Canadian market, Brad Treliving's departure from Toronto, Mike Gillis' outlook in the role and more.

Got four games in Stanley Cup playoffs tonight, and a bunch of GM vacancy still out there. There's our TSN Hockey Insider, Darren Dregger. What's happening? Dregs. Oh, you know, just getting ready for another barn burner or free tonight, right? Montreal, Tampa Bay. It's going to be exciting.

Not the hockey. O'Dog and I talked about it on the podcast earlier today. I mean, the pace has been terrific. The entertainment value has been there. There hasn't been a whole lot not to like. I mean, we always start to pick on the officiating, right? and the video review process, as we saw last night in the Ottawa Carolina game, but beyond that, man, the hockey's been rocks.

Dregs, is there any, like, is anybody going to be looking at last night saying we need to take a look at that, like, from the league side, or is it just one of those things that was somewhat confusing? It's a part of the game, and that's just the way it goes. Like, you think anybody from the league was like, I don't know if we can continue to have this? Like the offside call you're talking about in overtime? Yeah. Yeah.

Yeah, the offside and all that went with it. Well, look, I mean, I don't know this, so I'm not going to state it as fact. This isn't reporting. I'd be surprised if Tom Dunn and the owner of the Carolina Hurricanes didn't make some inquiries. You know, now that his team's won, he may loosen it a little bit. A little bit. It went his way in the end. But it is an area of concern that, look, I would say hockey operations,

Colin Campbell, the head of hockey ops, you know, shared when that office. side review was instituted many, many years ago, okay, be careful what we wish for here, because we're going to have no choice other than dissect it to a millisecond a fraction of a centimeter, whatever description

you want to use. The challenge that I would have and had last night and watching that is, you know, you've got the great experience that they have in that situation, but at the end it's kind of a judgment call too, right? You know, you're looking at the areas of criteria, the constitute offside, okay, possession, control, all of that. And the issued statement from the Situation Room was, according to the rulebook,

their interpretation was that Jordan Stahl didn't have control of the puck. How do we know what Jordan Stahl's level of control is? I mean, we're talking about, you know, top-end players here, right? Now, if that's Connor McDavid or Nikita Kutrov or an elite skilled player, not that Jordan Stahl isn't a skilled player, but how do we know, what their level of control is, and exactly in the moment, what's going on between their hands and their ears in trying to make that play. And then you get into the time sensitivity of it all, too, right?

Like, I mean, what were we talking here? Well, it took a while. And exactly, after the play had already been in, like there was a semi-breakaway that got a penalty shot called on it, and then they recycled the whole thing. And my issue has always been they lose sight of the fact that it's entertainment. That's the business you're in. and there's an OT winner, the place goes nuts,

and then you review it and call it back. It's not good for business. It's just not. And I understand why GMs want it, and that's every GM we've ever talked to. He said, I want the calls to be right. Good for you. You don't own the league.

Like, of course, GMs want it. This is where it's the responsibility of the commissioner and the owners to say, what's in the best interest of the product? And I don't believe the product was served properly last night. But you know what the flip side is, right? And we're reminded of this by the commissioner's office, by Colin Campbell,

everybody involved in this decision making is, okay, if we get it wrong, you guys in the media, myself included, are going to murder us in this process. You know, if that goal stands and Ottawa finds an offside

after the fact, I mean, okay, granted in this situation, call it the way that they did, issue the challenge so that they have a look at it, you know? Credit in the process to them determining that there may have been offside on the play, but that's that's why they go through that process as painstaking me as they do

because if they get it wrong we're going to be the first column of yeah sure we but get it right then you know it's simple I expect your officials to get it right it is true but I mean they do a really good job the hardest part is they're doing it in in real time and then you go back and it's five to eight minutes and some of the fans I guarantee you were in their cars yes oh they're gone they were out of there now would they let them back in That's the interesting part. Like there's probably people that were pissed going, I want back in. Probably not.

No, usually you're, that's generally the policy. You're out. You're out. And you know what those people that work at the rinks, like, that get the vest, they're going to have a power trip going, no, no, no, no. I guarantee you there will almost be a few fist fights. But, Dregs, I wanted to go to the GM search. You know, I mean, that's probably be the biggest hot topic throughout the league outside of the great games

going on. Right. You know, Kevin Adams' name being floated out there. You know, I wouldn't say household names that have been linked to the Toronto Maple Leafs. What do you make of all of what's going on here? Well, let's start with what we know. And I think it was the athletic who first reported that Kevin Adams has permission to speak with the Vancouver Canucks.

Buffalo granted that permission. And that's confirmed. That's real. And that makes a lot of sense. You know, there's history between Jim Rutherford, who's still in charge and Kevin Adams. And as we watch the Buffalo Sabres make their way through the first round of the playoffs, I mean, how do you look at their year and not give Kevin Adams credit for finally putting together a team that can win, not just in the regular season? Granted, there's a lot of hockey ahead, including tonight against the Boston Bruins.

But it's a wide net that they've thrown out there from Vancouver's perspective. So there you've got a general manager with a level of experience. I'm sure there are other experience guys. But they're talking to AGMs. They're talking to other relatively inexperienced guys. They're lucky internally. They've got Ryan Johnson there. wonder about Dale Tallon, who's associated with the Vancouver Canucks in some capacity, if not GM.

So they're interviewing already in Vancouver, and I think they're going to begin the in-person process as early as next week. In Toronto, man, we just, I don't think we want to go down that path yet again. There's, there doesn't seem to be a clear-cut favorite. There's a media favorite, and that guy's name is Mike Gillis. You know, we've all kind of anointed him. as the quote-unquote frontrunner, but yet they continue to interview people. Now, you know, you bring Gary Roberts and others through, as they did this week, you're not looking at those guys. Matt Sundeen last week.

They're not general managers or president. But they can't have a voice and they can perhaps occupy a position within the bigger framework of hockey operations. My understanding is Ryan Martin interviewed this week with the Toronto Maple Leafs, and I think he's also interviewed or is interviewing in Nashville. So those are some of the fresh names, I suppose. as we can add to the mix there in Toronto. Darren, how do you balance the idea of bringing in a relatively unknown type of executive? Because Brian was discussing it earlier.

I might have been Jamie. Yeah. How it might be just better to have somebody fresh as opposed to a former player, somebody with a name. Yeah. Like, that could work out, and that might be a little bit more forgiving for the fans if things don't work out. But it also could be risky if things don't work out. people are going to go above that and say, what the hell were you thinking hiring that guy? Yeah, so as you're asking the question, oh, this is what comes to mind.

Brad Trillivian is a general manager with a wealth of experience. Let's call it that. I mean, you know, beyond the days in Calgary, he was an AGM with Arizona for a long period of time, right? So he worked his way up the ladder. When they cut Brendan Shanahan loose, my understanding is that there were certain situations where at times, Cury Living maybe was a bit overwhelmed. Not by the hockey side of things, right?

Again, he's a general manager. He's worked in the trenches. You know, he's managed drafts, trade deadlines, free agency, all of that stuff. But I think it's not just Canadian market. When you're running hockey operations for the Toronto Maple Leafs, that's an entirely different beast. It's not one of 32 general manager jobs.

In which way? Like, what do you mean by that? Well, because you're, you're, if you don't have that go between, and I guess in this case it can be Keith Pelly, but normally it's somebody again with a high level of hands-on hockey experience like a Shanahan, right? You look at the Montreal Canadiens. You know, Jeff Gorton still likes the juice, but he gets a little bit of that as head of hockey operations in Montreal. But he's got Ken Hughes, who's got multiple layers of skill sets there that he can lean on.

but he's doing something different that Gorton isn't doing, and Kent Hughes doesn't have to deal on a day-by-day basis with Jeff Moleson, the owner, right? You know, in strong Canadian markets, that business aspect is a challenge. Because, you know, if you're an owner, you're a member of the Rogers Brain Trust here, right? Of course you want to have a say. You don't want to have a say on who's on the power play or what trade should be made or not made, but you want to be in tune, right? But what if you have a suggestion?

Shouldn't that suggestion go to the head of hockey ops? And then that guy, person, can filter that away from the general manager unless it's legit, and it's something that, hey, you know what, that's not a bad idea, I'm going to pass that along. It's a difficult one. It was hard at times for Trilling, so I find it more difficult to appreciate how difficult it would be on a guy with far less. Do you get the impression that Keith Pelley and Rogers are aware of that?

In other words, are they going to hire two people here to make sure that they rectify those problems? Because ultimately they're the ones that need to know that if there's an issue here. Not initially. That wasn't the plan. Isn't the plan. But, you know, again, if we want to give at least some credibility to the process and it has been exhaustive. Like Pelley and company have talked to how many people I'm sure it will be disclosed, you know, when the process is over and they've hired their general manager, maybe they've realized through this process that, okay, well, this candidate was really, really good. We feel strongly about that person being the general manager.

But then we've got Mike Gillis over here. Again, you know, he seems to be the media favorite, you know, and lots of reporting on him actually wanting to be the overseer. Well, that makes some sense, too. So initially we didn't want to hire both, call it whatever it is. I mean, I keep going back to the label is. Whatever the label is, it doesn't matter. But maybe they've learned in this process that, okay, well, maybe we do need that

as long as whoever that overseer is can work shoulder to shoulder with Keith Pelley. Because self-awareness is, I think that's the first step that needs to happen here. Like from ownership, Pelley, the board, et cetera, determining, you know, what is in the right, what is in the best interest of the whole hockey operation. And, you know, with Gillis, we've been saying it collectively, the three of us for weeks. I don't understand where his name came from. I don't.

He hasn't been in hockey in 12 years. Dude, how did he pop out of the sky and he's become this guy? I don't remember. Has he been interviewed elsewhere for other openings over the last decade? Like, I know we hear Shirelli's name all the time. And we hear, you know, you'd hear we joke about Fergie. Hey, John Ferguson's coming in. I don't recall the last.

last time it was like, man, Gillis, it's between this guy and Gillis six years ago in this town. Like, how did this happen? Like, does he know Keith Pelly somehow? Well, I think you got to know him. And true or not, I, you know, I heard that there were discussions well in advance of True Living being let go between Pelley and Mike Gillis. Now, you know, I'm sure that Mike has interviewed in other vacancies between now and his time with the Vancouver Canucks.

You know, and not as public, not as under the microscope as the Toronto job would be for a myriad of different reasons. I guess the question that I have, though, is why hasn't he been hired? Yes, exactly. And now, I do know, and again, I talked about Ken Hughes, and we often look at Bill Zito because now he's a decorated general manager with back-to-back Stanley Cups. But, you know, if I'm Pellier or I'm, you know, ownership. on the Rogers Group,

I have no problem looking at, again, a layered executive, right? Yes. You look at Billy Zito. He's a lawyer. He was a high-profile player agent. He went through management training in management with Columbus

under the tutelage of Yarmou K. Kalina and then became a general manager. So he can lean on many different things. Well, Mike Gillis has a lot of that, you know, including a former playing background, right? So I have time for the skill set, the resume of Mike Gillis, but I just don't understand why he hasn't had a job in a decade. Yeah, 12 years.

Yeah, over a decade. And furthermore, how he leapfrogged every executive currently in the NHL, and he's up for the most sought-after position in hockey. Yeah. How's that possible? It's, oh, you know what, look, again, I'm not trying to devalue Mike Gillis because... I'm not either. It's just curiously.

He pops up out of nowhere. Kind of, but again, we go back to that media availability, where Pelley made it abundantly clear how heavy he believes in analytics and data. And you do go back to the time of Mike Gillis in Vancouver, where he was ahead of his time, right? All the sports science that the Canucks leaned on, the sleep studies, and all of that stuff, I mean, teams weren't. If they were doing it, they were doing it somewhat quietly, right?

Sure. But he made it seem like he was way ahead of the game, and this is direction of the future. That's fine, and that's great. He's a mad scientist, and he was way ahead of his time. Okay? Yeah. The team went to the finals one year.

Other than that, what does this guy have in his resume where you can put the two together and say, that's why you've got to get this guy and all of his data solutions and everything. I can say that I do experiments with smoking bubbly stuff in my garage, but if I don't do anything with it, who gives a rat's ass? See, here's a question that I'll put to everybody, though.

Is there anybody, and it's an honest question, is there anybody out there that fits the exact bill that we're all talking about, the experience, and oh, what you're talking about? What is the guy done? So if Doug Armstrong was unemployed, maybe that's the guy. But is there anybody out there that fits every checkmark? If you've got a five, you know, a five bucket list. Yeah. Well, not necessarily that's unemployed, but, like, have they looked into poaching anybody? Exactly what I would do.

Like, if you would leave. Yeah, like, can you not? It's tampering, isn't it? But they did it with Burke back in the day. I mean, they, they, it's a wink, wink, nudge, nudge, I'm out of here. I'm going to Toronto. I mean, yeah, you'd have to do it above board. You'd have to see permission and, and speak to those candidates if you were given permission.

But, you know, look, I, again, I, I appreciate. I think it was Jonas wrote about the guys that, you know, they should go after. And I think who was it, Kelly McCrimand, Julian Breeze Blah, and whom I miss. Yeah, maybe Bill Zito. I mean, yeah, exactly. Of course. But, again, for me, it's somewhat a show of the arrogance of Toronto. Yeah.

You know, like, why would any of those guys, aside from, and I will say this, because Brad Trilliving is living proof. Brad Trilving knew there were going to be challenges. Even, you know, he came in under the leadership of Brendan Chanahan. But there is something about the reality of potential in becoming that general manager to lead this team to another Stanley Cup championship. Yeah, it's the white world. That is intoxicated for all of these executives.

Absolutely. Because other than that, why would you leave Tampa, Vegas, or Florida, exactly. Exactly. 100% yet it is the white whale of the league and maybe the money possibly it's more up here anyway we'll see yeah some one of these days we'll have a resolution they'll hire a few people sooner than later sooner than later all right treks good seeing you i'm luke wilson join me each week for film never lies since retiring from the nfl i've had a lot of my mind and now got my own show

so if you're tired of lazy takes if you want honest conversations join us each week film never lies available on all TSN platforms in the IHeartRadio app.