OverDrive - Dreger and Johnston on Connor's extension in Winnipeg, Hutson's possible deal and Cowan's status

Episode Date: October 8, 2025

TSN Hockey Insiders Darren Dreger and Chris Johnston joined OverDrive to discuss Kyle Connor's contract extension with the Jets, the Maple Leafs' matchup against the Canadiens and Easton Cowan not playing in the season opener, Lane Hutson's contract expectations, Mattias Ekholm's deal with the Oilers, Connor McDavid's contract ripple effects, the Maple Leafs' season overview and more.

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Here's the insider roundtable. Darren Dregor and Chris Johnston joining us now here on the Maple Toyota Hotline. Look at these guys. Look at this crowd. I love it. How we feel in this afternoon, boys? I'm feeling pretty good. I'm parked at a Cabellas. I'm going to say all's well here down at Scotia Bank Arena.

Okay. And Dregs, you're in Winnipeg? Is that where you are right now? Where are you? Yeah, yeah. I mean, I'm in the Winnipeg, specifically. I'm in a parking lot at Cabellas. I got the work done early, did a bunch of sit-down interviews with all the stars of the Winnipeg Jets. Obviously, I had to chew on the Kyle Connor signing, and then after that, Jack Eichel. But just a bit of downtime here and then get ready for their home opener tomorrow. Okay. Beautiful. Well, in terms of those signings, I guess we'll begin with you, Dregs. This is a theme happening throughout the league, where if you're a star,

player. You stay in your respective market. Player wants to stay. GM and owner wants to keep you. And outside of Mitch Marner, everyone else has been kumbaya so far. What do you, is this just the new NHL and for how long is this going to

happen before a superstar decides I'm actually going to test free agency? Yeah, I mean, that's a good question. And there's some good players that are obviously entering the final year of their contract that will be decent unrestricted free agents, but to your point, Brian, not to the level of Jack Eichol, or obviously

Connor McDavid, you know, Kyle Connor, Caprize off in Minnesota, but these are all cornerstones of their franchise, right? You know, no different than Caprizov in Minnesota. The Winnipeg Jets couldn't really look into the crystal ball and see a future, productive future, without Kyle Connor. And Kyle Connor embraces what Winnipeg is all. about. He's one of those guys like Connor Hallibuck likes the outdoorsy sort of life. He's got a young family so it makes sense for him

to likely tie his wagon for the rest of his career to the Winnipeg Jets. And I would apply that same long Jack Eichol. Now Jack Eichol's getting more money, $108 million dollars, a heavy front-loaded contract, right? But he

sees the Vegas Golden Knights as near perfect fit for him. The Vegas Golden Knights see Jack Eichael is a perfect fit for them. So why mess with it, right? Just get it done and live your professional life the way you want to. We know that you're a contending team and you have a chance almost annually to win a Stanley Cup. Dregs, did any of these guys have a mandate where it was like this better get done before the season

or they pulled the Phil Castle and they didn't want to talk throughout the season? It seems like prior to drop of the puck they had to get these done. Was that a mandate for any of them? I didn't get that sense. I didn't. Look, I mean, you know, specific to Kyle Conner here in Winnipeg, they were talking on almost a daily basis, Kevin Shovelay off in the age there, Rich Evans. And as I said, you know, Kyle Connor made it clear he wanted to get a deal done in Winnipeg. However, the business side of things dictated that for the first time,

the Winnipeg Jets had to pony up a signing bonus. $41 million. You know, it's not chum change. um so there was an appetite to get it done nobody wanted it to be a distraction and in a small market like winnipeg i can tell you guys this is like going in the game on of a playoff series like the city isn't electric but there's a buzz because of this contract extension so i i think mid david didn't want the distraction and jackichael's probably the same they just wanted to get it done but i do i don't think there was an actual mandate over with uh darren dregor and chaston

And C.J. you said you're down there at Scotia Bank, and we were talking about this, you know, the Leaf lineup prior to you guys coming on. And we had Craig Baroube on yesterday, and, you know, he was pumping the tires of Easton, like he has for three weeks, and saying he's ready, and we want him up here, and maybe he will be available, kind of tipping his hand a little bit. And then Cowan gets called up tonight, and he's with the team, but he's not in the lineup, which would be Barube's decision. So how do we juggle this?

Why does Barubei love Easton Cowan think he's ready for the NHL, but he's not playing tonight? Well, I think two things can be true at once. The Leaves feel that Cowan performed more than well enough in training camp that he earned a spot on the team. And that's, you know, that was reflected in the way Burubay has spoken about him really since the early days of camp right through to hear the start of the season. You know, but the flip side of that, I think at the same time is, you know, they don't want to put too much on his plate. that they're kind of going through, you know, those two things. And, you know, really, it's kind of a weird last few days I have to feel for Easton Cowan because he had such a good camp.

It was all positive. And then because of the way the cap works, the Leaf sent him down as part of the gymnastics they were doing, you know, just for a day, but, you know, it means he couldn't practice yesterday with the team and then rejoins them now. He's a scratching game one. I mean, I would think he's a good bet to play in game two for them this weekend in Detroit. No guarantees if they win six or seven one tonight and everyone has a good game. It might be tough to take someone else out of the lineup at that point.

But generally speaking, they obviously want to get them back into action here with the team, I think, pretty quickly. And if not, I'll go back to the HL. But the Leafs are in a tough spot with this player because I do think that they're kind of wrestling with what's the best for his development. But also the league has changed the rules this year. And if any player gets sent to the HL, they have to play a game now. So it's not like you can send a guy up, you know, down one day, up the next day, and all the stuff that we used to see in the past. And so when it comes to Stigalan specifically, I think where you're worried about

or you're very cognizant of his development, you know, they're going to really have to plan when he goes down, when he comes back up. And so, you know, I get the sense that they don't have the exact plan in stone just yet. And, you know, they just want to ease its transition. But, you know, it's got to be a weird feeling for him. what they say because everything was so positive in these last few days and you know all of a sudden it just feels like he's on the

outside looking in without a real clear explanation. It's so weird C.J. because he was tied to his linemates, Lawrence and Lawton and it was like everything was positive and when that went down all a sudden he couldn't play in the NHL which is a weird vibe for such a talented player

and if the Leafs do have success tonight and they don't change their lineup you would think that's not good for Cowan. He's probably got to go down this. The one thing for his development is he's got to play yeah right and i do think that that's not a bad big picture if he plays spends the first month in the hl i don't think that's the end of the world by any means i don't either and you know the best thing the best thing for east and count is he knew this year right there's there's none of this junior stuff anymore like he knew he's becoming a pro hockey player you know

with the way the leaps have a set up here he knows he's going to live in toronto and it's just a question of is he with the marlies or the maple leaves at any given time and And, you know, he's critically important to this organization. I mean, when you're in the spot, the Leafs are, you just traded away so many picks over the years. By virtue of that, you're not going to have a lot of prospects. And he's, you know, obviously at the top of their prospect list. He's moving into a player now.

He's not just an idea of a future thing. But, you know, getting him up and running, I think, is they're going to do what they believe is best and be very thoughtful of this specific player. It's not just about the team. So, you know, I'm willing to give them kind of, kind of a little bit of time here to see what that looks like. But, you know, I can't imagine you're going to see them scratch too often in the NHL. I think if that's the case, I'll just be playing games down at, you know, with the Barleys.

With Darren Dregor, TSN Hockey Insider, Chris Johnston, our TSN Hockey Insider, Leaves have tonight on TSN Radio. So from Montreal standpoint, Dregs, they had a phenomenal stretch run down the stretch last year. Unbelievable, they make the playoffs. They go out there and acquire Noah Dobbson this year. where what do you think the next step is here for the habs like if they officially recognize themselves as a playoff team do they feel like they have to continue to prove that you know they're still young damadoff's here now lane hudson going into his second year like where where do you stand on on the projection of montreal and the business that maybe still has to be done there yeah no there's still work to get done there uh they have some interesting storylines right we're still wondering you know about their number two center and In fact, you're looking at that second line in Montreal, and you could, in theory, put question marks beside all of those guys. And, you know, we've spent a lot of this, you know, preseason training kind of talking about Kirby Doc and Patrick Lainey.

And, you know, there was some concern. They need Kirby Doc, a veteran experienced player with injuries behind him to get off to a good start, right? So by initially having him penciled in with Demidoff and Patrick Lainey, they felt like maybe that saddled him too much with, the defensive cleanup, playing with those two guys. So it appears they're going to give them a different look, but they have comforting going back to that line. I look at their defense, and I mean, their top four is rock solid. You know, they've got Kerry in their third pairing with Arbor Jackie,

and maybe that's a temporary situation, I don't know. But I think that there's a real belief that they can go deeper than they did a year ago. I think the way they played in the second half and how things came together late in the season last year, maybe went a little bit beyond expectation, but that's not where they're at right now. That's not. They expect to be a playoff team, plain and simple. And in the meantime, they've got that Lane Hudson Contract Extension, which, unlike Eichol and Connor and Connor McDavid, I wouldn't expect that this one is going to get done anytime soon.

Why is that, Greg? That should be a layup, shouldn't it? after what's gone on the last few days, isn't that contract a lay-up for those guys to get him done? Well, I mean, what is that lay-up, eight times ten, no? Because no Dodson's nine and a half, right? Yeah. Well, if that's what he wants on the paper, then that's what you've got to put on the paper. Yeah, I honestly, I think it's been reported on well and fairly.

There's a lot of emotion in that negotiation. You know, the family is heavily involved, and I think that wisely both sides have said, okay, let's just put on hold for now, right? Cortex represents Lane Hudson has come in with a team approach now. It's not just one agent. You know, Darren Ferris is overseeing it. Ryan Barnes is involved. There might be a meeting with Ken Hughes, a GM Thursday in Detroit, so tomorrow in Detroit.

They haven't officially made that so, but it's a bit of a spike. meatball right now as far as the overall look at this thing is. So I think they needed to calm down. Guys, what did you make of the Oilers continuing to do some business as the reverberations of Connor McDavid's contract extension continue to be felt around the league? How did you interpret Mattia Secombe signing up for three more years at $4 million, which is obviously a discount off his current cap hit of $6 million? And, I mean, is that a guy taking the lead of the captain?

Or is that, you know, a little bit of a risk for the oilers, given the fact that he is 35 years old and, you know, tacking three years on is going to put him into some precarious territory with injury and age? Well, I see Dave as a direct, you know, fall trickled out effect. I'll put it from Carnar McDavid. I mean, you're right. There's obviously risk at his age. And, you know, he missed considerable time last year within.

injury and, you know, a lot of hard miles there, you know, been part of some long playoff runs and he's deep in an NHL career. But, you know, the flip side of that is this is not a free agent class that shaping up in 2026 as being overly strong. And in an alternate universe, if he wanted to test free agency, I think there would have been more money out there for a player like Matthias Atcombe. But he and his family love Edmonton. And I think it's a lot easier to commit to stay with the Oilers when you know McDavid's going to be there, you know, and you kind of have a better sense if you're in his shoes, you know, what those next few years are going to look like for the team.

So, you know, I do see this as following the lead. And probably we can call this a small hometown kind of discount from at home because, you know, I know off the ice and speaking with him a little bit, that that's been a place that actually reminds him, he said, of living in Sweden. I think he's really appreciated what it's been for his family and the lifestyle. And now the team, you know, has every reason to think they can keep being a competitor for the Stanley Cup. and that sort of cinches getting that deal down. Well, I'm curious if, you know, in a different world of McDavid told them,

hey, I'm leaving after this year, would they have gone about business differently? You know, and I think that's kind of what you're driving at, Dave. Like, you know, McDavid specifically said, I like being here with the core guys. And then immediately Walman signs, immediately at home signs. In other words, is McDavid contributing to that? Does he have that kind of power? Is there a LeBron James element to this? where we goof on LeBron a lot.

Well, he's getting this guy fired. He's getting that guy signed. He's getting that guy traded. You mean going to Ackholm and saying, I did it? You better do it too. Well, I mean, or, hey, keep back home because I'm staying and he's a core guy. You know, and if, like, is everyone on board with all this? Or is it, hey, we got to keep McDavid happy because he signed for 12.5.

Treggs, you can start on that. Well, maybe a little bit of everything. Do I think that, you know, Stan Bowman and Jeff Jackson go to Connor, David and make personnel decisions, roster decisions? No. Do I think that he historically has had input and at times isn't afraid to share his opinion? Yeah, I think that all of that is true. And why wouldn't he, right? He's the best player on the planet. He's a captain of the Edmonton orders. But Mike Johnson made this point on Monday night on our preview show, and I think it's valid. It was way easier. Obviously, Bowman and Company had been in negotiations with Jake

Walman, right? You don't announce Connor McDavid and then short time after Walman's deal gets done. But Connor would feel good knowing that, all right, we've got Walman done. Now we have Mattias Ekham. These are two pieces that I'm comfortable with

that we can win with, but you're not done yet. Like, are we good with goaltending? Let's see in 2025 games. You know, do we need pieces up front? Well, given a level of inexperience with certain players up front for the Edmonton owners. Yes, Dan Bowman has some work to do.

If not this year, then in the next two, to keep McDavid happy. C.J., we'll get you out of here with a question about the game tonight. You're down there at Scotia Bank Arena. This is the first time in 11 years. Brendan Shanahan is not running the whole operation. Do you anticipate it looking, sounding any different tonight, in terms of opening ceremonies, in terms of how they unveil things? Game-ops.

game ops because he was involved in that like heavily involved in that the Keith Pelley era instead of the Brendan Shannon area do you think it'll be different for the fan experience and what we notice at night one it's a great question honestly I hadn't considered that angle of things

I do think it's possible I know from speaking with you know people around the Leafs that they they've felt some changes behind the scenes not just pursuant to to Brennan Chanan being gone but with the change in ownership and Rogers you know, having a bigger influence and an ownership stake in the team.

And so I do things are, I do think things are shifting a little bit. But, you know, I don't know if that's something we'll see or feel in this game. To be honest, I'm most wondering, like, what's the vibe going to be like in the ring? Is everyone going to be watching a baseball game on their phone? If the Jay's, hopefully, Vladdy hits another big old runner in the game. Are people going to react to that? Like, it might be kind of a strange home opener just because there's such a big baseball game going on at the same time. But, you know, it's definitely the start of a new era.

I can even say the little bit I've been around Leif's camp that there's been, I would say a little more access granted to the reporters. I think that that's something Keith Pelley, if you remember, talked about in May, but it seems like they're extending an olive branch. I'm not scanning that on Brett and Shannon. It wasn't his job to do those types of things. But certainly, you know, there's big changes behind the scenes with the organization. And I think it's only a matter of time before we see some of those things manifest itself.

and things that we can see or get a sense of at least in the role I have here. All right. All right. Well, night two of the NHL. It's going to be a blockbuster this evening, man. You got Leaves Havs, Battle of Alberta. You got Mitch Marner making his debut in Vegas tonight. It's going to be awesome.

All right, boys, we'll let you get back out of it. Thank you for doing this, as always. Thanks, guys. There they are. Thank you, see, guys. The insiders. Chris Johnston, Darren, joining us from the Maple Toyota Hotline. Get in and go where adventures take you in a new 2025 Tacoma for Maple Tacoma or Maple Toyota near Canada's Wonderland and the Maple Auto Mall visit MapleTotida.com.

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