OverDrive - Dreger on Hellebuyck's future in Winnipeg, Bobrovsky's next steps and the Maple Leafs' deals

Episode Date: June 26, 2026

TSN Hockey Insider Darren Dreger joined OverDrive to discuss the biggest moves around the NHL, Connor Hellebuyck's future with the Jets, if Winnipeg will make a deal and the direction for the roster, the Maple Leafs' number one overall selection, Sergei Bobrovsky on Toronto's list, the Panthers looking for major moves, Matthew Knies' future, Jason Robertson's contract perspective and more.

The biggest soccer tournament is... Amazing! Did you see that goal of the century? Don't tell me... You missed it? The diving header in the 93rd minute? Which left to penalty kicks? So much pressure. So much.

Trauma. Every minute. Soccer connects us all. Get in the game. Get on Canada's fastest 5G network. Visit a bell store or bell.ca for details. Bell. Connection is everything. Where the Leafs are about to pick first overall.

And Darren's joining us in studio. doing, Dregs? I'm doing okay. You know, it's kind of warm in here. Why is the air not in here, Brian? It's a good question. We have to call Montreal, Dreggs, that's why. Yeah. Yeah, it's kind of a bizarre system because it's gone both ways where we've come in and it's incredibly warm,

it's incredibly cold. Well, I complain to Doogie, doogie goes, let me call up somebody in Montreal and by next week we'll get that sorted out. Not to disparage the World Cup crew in Studio 6, but it's as hot in Studio 6 as it is in here. Really? And that

does not happen on James Duthy's watch. Ice cold. Does not happen. Ice cold. Yeah. I don't know how to explain it, but how are we feeling about this evening? I know Noodles has been calling a shot for about 12 years now that all hell is going to break loose.

And he is a believer that tonight, although I guess it's been breaking loose all week. I think we've been consistent. You're right, Brian. We've been consistent. But drags any, I mean, any sniffing that, you know, a top 10 pitch. or go, top five pick maybe, that gets moved? Well, there's an appetite for that, right? It feels like we've been talking about this for several days.

It's not looking great that Winnipeg has an example. You know, I've been nibbling at the Connor Hellebuck scenario, as many of us have, and where might be the best fit, who's most interested in all of that. And I do think that the Buffalo Sabres have been a team that has been circling around Connor Hellebuck. Would you give up the fourth pick overall, you know, the pick that they're acquired from the Chicago Blackhawks as part of a package. If Overdrive had been around 11 o'clock in the morning,

I might have said, yeah, I think it's trending in that direction. Now I don't, I'm not as confident in saying that. I'm not as confident in thinking that these two teams are going to be able to get something together in time for the opening round. But we'll see. I mean, I qualified every single year around this time of year by simply saying, all it takes is a phone call, right? One, because you've nibbled at the parameters of what action.

trade looks like when you're talking about top-end players or goaltenders. So all it takes is one guy to go, okay, yeah, you know, I'm turning away from this team over here and that opportunity, so I'm going to focus on you, let's get this done. I'm not saying it's going to happen, but it could. Darren, Brady

Kachuk made it clear. He said, I don't want to start the season with the Ottawa Senators. Dylan Larkin has done the same with the Detroit Red Wings. Is it clear on what message Connor Hallibuck has sent the Winnipeg Jets? Does it mirror those other two or is it a different message? It's similar I think oh and I'm hedging here because

I don't believe that there's anything official. There's just that sense, right? And maybe it's more similar to the conversation that Brady Kachuk had with the brass of the Ottawa senators different than Dylan Larkin or Darnell nurse. You know, Larkin and nurse just formally made a trade request. Yeah, look, I mean, Connor Hullabuck came out at the end of the year. He said what he said. how disappointed, unhappy he was, and I don't think that he is relented on that position even a little bit with the management of the Winnipeg Jets or with his teammates.

I think that he's been steadfast in that. So, I mean, are we dealing in semantics? If you know that the player isn't happy, you know, when is the best time to deal with it? And it's probably around now, because you've got all the activity leading into the draft and free agency. And on top of that, that free agent pool, as we know, is getting

less and less interesting on a day-by-day basis. So I think the teams that have assets like this and they know that they're no longer happy or doing everything they can to exhaust possibilities. What is the potential domino effect in Winnipeg if they trade Hellebuck? In terms of being competitive in the future.

Yeah. See, again, I think it depends on what you're getting back here. You know, in a perfect world, you get a number two center that comes back with that. And obviously you need a goaltender. They've got Connor Helbuck and they've got Comrie. So you'd need a goaltender back. If you're not getting a number two center, then I think that you have to get more creative.

I honestly believe that that market, if we go back to what I said earlier about Buffalo, and let's just think out loud. This is my raw pure speculation. So you get the fourth pick overall. You get UPL. You'll go back a lucan. You know, maybe you get a prospect.

You know, is that good enough? Is that good enough? to sell that because if you don't have to throw the eight pick into the equation, now you're drafting four, you're getting a hell of a hockey player at four, and you're probably getting a real nice ad in the eight spot as well. I think you can sell that to that market. I do, I do. And the goal-tending, and then you've got to dabble and, you know,

add another depth center and maybe some other pieces up front and things like that. That's where it gets tricky, though, because you're not, you're telling your market, we're not going to be a playoff competitive team next year, It's unlikely, but we're not that far away. And look, Shoubledayev goes through this, and he's gone through it in the last week in having trade conversations, there wouldn't be another team in the National Hockey League that has more blocks in front of them than Winnipeg.

Every player in the league that has the luxury of a no-trade list, has Winnipeg on that list. Every single player. So it's almost impossible when you're trying to add pieces by a trade. Well, that's exactly what makes it so complicated. Like even if hell bucks out, and they're like, well, we'll go find other players. How are you going to do that? I mean, it really is a tricky situation for them up there.

In terms of, you know, where the Maple Leafs currently stand, I saw they traded Erson to Ottawa. They get that fifth round pick back, so basically what they traded to get the rights to radish. Where do things stand with that? Like, they have the first overall pick tonight. Do you think they'd want to overshadow that moment with a deal beforehand? I mean, I don't think so. I mean, it's been reported. We know that Chikin, whoever else, accompanied him to the investigation in Whitehorse.

You know, do you go to those lengths to get to know the background of Gavin McKenna? You know, but I'm no draft guru here. You know, what if you look at Stenberg and you go, he's pretty damn close? He's pretty close. Do you even go as far as to having a conversation with Mike Greer about dropping down a notch? if you're not convinced that Gavin McKenna is worth a splash and all of that. Tika, my understanding is he's been involved in a bazillion different trade scenarios, conversations.

So when I saw the trade today where Erson goes to Ottawa, this was a plan all along, maybe not necessarily to send him to Ottawa, but the fact they weren't going to qualify him. And I thought, for whatever reason, you know, despite the fact that they've got some depth in the goalie position now with what happened in the American League, I'm like, hmm, all this Sergei Brabowski noise out there, maybe there's something to this. And I was told, no, it's unrelated, but then an outside source said, yeah, well, that could be true. But if Barowski doesn't buckle and end up resigning, extending with the Florida Panthers, then Toronto most definitely is a team, as many have speculated on, that is pretty high on this list.

Gregs, with all the talk, like, you know, it seems like there's the five destination and all these players are wanting to go to and teams not wanting to. A guy just turned down a signing in Seattle today. Yeah. Like, is this filtered up to the league? Like, does it gotten people's attention where they're like, there's something to do about this? Or is this is just the way it is and you guys got to deal with it? I think it's the lateral.

And I haven't had a conversation with Marty Walsh, executive director of the NHLPA, but for whatever reason, when I see what's happening, I'm thinking of Bob Goodnow. God rest his soul, he's probably, you know, smiling down and going, this is beautiful, because players have actually now taking control of what their career path is. And it used to be you grab every single dollar that you can get. Well, that's the easy part. Now guys are doing it when they're two years out from a contract extension or an expiring contract. So I don't think that there's much that the league can do about that and the individuals can do about that. But I think we're talking about a select crop here too, right?

You're not getting middle-of-the-road players doing that with teams. You know, you're talking about the best of the best. We're flexing that sort of muscle. And I don't know that the NHL has much pushback in that regard. Greg, so we were talking about the parity in the league and a lot of the moves and all of that. Is there a team that you would maybe circle and say, you know, watch out for X, Y, Z, like kind of off the radar. You know, everybody's, obviously, we focus on Toronto and, you know, some of the teams. Is there somebody that you go, hey, keep an eye on San Jose or somebody like that that might be active?

Well, those teams for sure could be active. San Jose, I think. What about Seattle? Oh, alluded to it earlier. I mean, Jason Robertson pushed away from an eight-year, $120 million deal. And the sense I get as to why is he wasn't bullied into it. I mean, there was a trade executed between Seattle and Dallas

that wasn't going to be formalized unless the player accepted the contract extension. But Seattle steps up in an enormous way, enormous financially, because Seattle knows that they've got to go pedal to the floor here. There's no other way. You know? And look, I think Robertson looked at it and went,

well, there's a couple of things. I'm not convinced that Seattle is going to be a contending team anytime soon. And I'm also not ready to make an eight-year decision at this point. You know, it's not like this has been on his radar for days and days and days, so he's had time to digest. So Seattle pushes away from that because it's not happening, but, man, Seattle has got a strong appetite for something. We don't quite know what it is yet,

but if there's that level of player, I mean, Robertson's pretty lofty when you look at how consistently is offensively. I think Seattle is a team that, again, if they can get in there in some way, shape, or form, they're definitely going to try and get something big done. Yeah, I'm wondering when the Montreal Canadians are going to kind of join the dance party here. After the season they just had, they have a ton assets, they got a lot of picks,

and I'm thinking, I have to believe they feel pretty confident that they have the core in place that is going to, at least, to afford them a playoff spot next year. Everyone knows what they'd be looking for, that second-line center, I think. Like, are they going to just continue to slow play this, which may not be the worst decision? Like, let Hage show up

when he's going to show up and the other young players, or do they decide, you know, forget it, we're going to floor it here ourselves and see if we can really push forward. Well, they've been trying to do that. You know, they've been trying to do that, but, you know, you have to have somebody to dance with. You know, I think that there definitely was interest in Hecher, doesn't look like

he's going anywhere. Dylan Larkin made it abundantly clear that, you know, he's got a select few teams that he's willing to go to. You know, I think that they've more or less kicked tires on Vinny Trocheck with the New York Rangers. You know, he actually makes some sense, even though I believe Montreal is on his no-fly zone. I think that there's some flexibility from Trochex perspective. He makes some sense because he's an older guy established, and maybe that buys you just enough time to get Hage up to speed, right?

but they're okay with where they're at up the middle of the ice. And so getting that number two center, they look at as a luxury item. They've certainly tried to play that game of acquiring that piece. But Jeff Gordon and Ken Hughes always have a cart up their sleeve. There's always something there. So if it's not a center because they believe that maybe Capitan with a little bit more experience can play an elevated role, they've got Hage coming, all of that. They might flip to the wing.

they might flip to the wing and see if there's something that's quasi-juicy available out there that isn't too free agency but maybe is there through trade. With Darren Dregor, you mentioned Sergey Bobrovsky and I get the impression his preference would be to stay in Florida.

If not, like I just don't see Florida starting next year with one of Bob or Halibuck and that. Like that's just what I assume will happen. You do, eh? I just assume that's going to happen. That's my... just based on their history and the way that they operate.

And the league just seems to be like, yeah, here, we'll help you out. You know, what do you need to do, Florida? We'll find a way to make this work for you. Well, you know, look, I mean, Billy Zito has been one of the teams that has been consistent in pestering shovel day off in the Winnipeg Jets. But they're not willing to give up Lundell, and that would be the centerman that Winnipeg would cover, obviously. So what other pieces can you throw into that equation?

And there really aren't any, because you're talking about futures. You know, Bill Zito can trade away his first round draft pick through 2013 if he likes. But that's not really helping Winnipeg. Not saying that that isn't going to happen. Let's just see how it plays out. But again, let's remind everybody here that Helplock is under contract through 2013. So if Winnipeg Jets don't get the deal that they need, as awkward, as uncomfortable as it might be for Hellie. I'm sorry, man, but you're under contract here.

We tried. Now, Brabowski, and this was pointed out to me today, as we know, the Russian players, man, they command respect. They want to feel like they're respected. And I'm not here saying that Florida is disrespected, Sergey Barbowski, but because they've had so much time,

he's had so much time to contemplate all of this, and that six-time-seven contract hasn't been realized in Florida, and that's initially what he wanted. Maybe he's going, oh, wait a minute here. I'm feeling a little disrespect in all of this, and maybe he is actually willing to leave. But it also wouldn't surprise me of, you know, they don't have that chair filled.

And Bob comes back and says, yeah, I don't want to go anywhere, anywhere. Let's figure this out. Dregs, I was trying to tell Hayes because he never played professional sports. What did that come from? I was trying to explain how pissed off. Dregs, you know me, and if I was sitting at home, and all I heard was my name being bandied about how they're listening to offers and that most likely I'd be moved, you know how I would

handle that. Yeah, like, where does Matthew, yeah, like, where does Matthew Nyes come into this where he just calls the organization and says, what in the hell is going on here? I committed to you guys long term, and now I got to sit and listen to this. I would not be happy about this. Well, that's why he's in Italy, right? I mean, with all due respect, that's why he's there. He's trying to escape some of the social media in ways.

And hey, look, players will say, I don't listen to it. I block it out. I don't watch all of that. Sure, they do. I mean, they do. And it comes back to them in varying forms through family or whatnot. You know, look, I think we've been consistent in this all along. And it dates back to the trade deadline when we know that Trilliving had considerable

conversation negotiations with Montreal, to agree with Buffalo, maybe there were some other clubs. This isn't new to Matthew Nyes. You know, John Chike's new general manager has to listen to the interest, but not one time, as he said to any club that's asked that, yeah, I'm interested in trading him. He says, no, that's not good enough. You know, if you want to acquire one of our best players

and a key part of our future, it's got to be better than that. So keep adding. And there's been ample conversation, but nothing that I'm aware of that Toronto is seriously considered, but that doesn't keep Matthew Nyes out of the crosshairs. It would be tough. Well, we'll see what comes between now and Wednesday, anyway. And then beyond that, there's always room for deals into the summer.

You know what I'm doing Thursday morning? Yeah, wiping your underpants, drip like you're drenching the underpants into a garbage can and throwing them out. Straight into the fireplace. Thank you for that. Have a great weekend. We'll do it again soon. Thanks, guys. Close your eyes, and you can hear the entire world come alive.

2026 FIFA World Cup is on, and you can stream it all live on TSN Radio. From the opening kickoff to the final celebration, every match, every moment. Listen to FIFA World Cup on TSN Radio. It's Canada to the Lift Off. Available on IHeartRadio.