We weren’t in the room with Brendan Shanahan and Kyle Dubas over the past few seasons when their relationship reportedly deteriorated as Toronto Maple Leafs president and GM, respectively. It’s thus difficult to assign blame for the erosion of what appeared to be a cohesive organizational power structure in their nine years working together. Was Dubas trying to overthrow Shanahan and take total power over personnel decisions? Did Shanahan’s emotional reaction to a request for a raise from his GM do irreparable damage to the franchise?

Questions like these are undoubtedly intriguing, but we don’t have enough information to speculate, despite the “open” address Shanahan gave last week, which clearly didn’t include every last detail. What we can say with a fair amount of confidence is that major changes are coming to this team. We already know a new GM will take over. It remains to be seen if support staff such as assistant GM Brandon Pridham and assistant coach Spencer Carbery get poached by other organizations. And many questions loom about the futures of Toronto’s star players, particularly the Core Four forward group of Auston Matthews, Mitch Marner, John Tavares and William Nylander.

…

But is that a deal the Toronto Maple Leafs can win? More specifically, is it a deal they can win in the present, reloading and still managing to contend?

…

After digging through all the major deals of the cap era, I’ve come up with five examples in which a team that was squarely in its Cup contention window made a bold hockey trade involving at least one core member. Here’s how the scenarios played out – from the perspective of the team in Toronto’s shoes.

…

Looking at the comparable trades above, it really does feel like Tkachuk is an anomaly. More commonly, when a team trades away core players that have helped them reach the precipice of contention, it ends up regretting the move. Food for thought if you’re the next Maple Leafs GM.

Frank Seravalli: For me, it’s beginning to tear this down and identifying the three, maybe four pieces that you’d like to have on this team in five years when you finally get to where you want to get to, and if you’re not part of that three or four member group, start moving them out.

Mike McKenna: Yeah, what you said just relates back to one thing, cap space and the vision of this team in the future. I think you have to trade Kevin Hayes, there’s just way too much friction between him and Tortorella all season long, too much smoke to the fire. Is he going to be there long term? No, so get the picks you can for Kevin Hayes.

And then I think you need to look at what Tortorella said, even on March 20th, that there needs to be some subtraction, so like you say, you’re figuring out who’s going to be there, and for me, I think you look right at that D-core. There’s $16 million tied up in three defensemen that were healthy scratched at some point last year. Sanheim and Ristolainen, long-term deals. DeAngelo, one year left. Provorov, two years left. I don’t care how you make it happen if you’re Danny Briere, you got to shake that up and move out some of that money somehow, someway.

I do think the team will be a lot better next year with Couturier and Atkinson provided that they stick around. I think you move Hayes, you figure out that D-core, and if there’s any other ancillary piece that Briere doesn’t see as being tangible, valuable assets down the road, clear that cap space, get some picks, get some more youth into this, because you know what, some of those prospects, they just straight up haven’t panned out for the Philadelphia Flyers. They need another reboot in that area.

Seravalli: What do you do with someone like Travis Konecny? He had a breakout year last year, 31 goals, 61 points. He’s already 26 though, and by the time you probably want to get this team to where it’s heading, he’s going to be 31. And not to say that he can’t be a contributor then, but with two more years at $5.5 million before becoming an unrestricted free agent, it kind of feels like, at that contract and that value, Travis Konecny’s never going to have a better value on the open market. Isn’t this the year that you’d have that similar type of conversation?

McKenna: Yeah, I think so. I think there’s different pressure points. If that is a direction the Flyers choose to go in moving Konecny, is it at the trade deadline next year? I don’t know, to me it seems more like either a draft deal or a free agency summertime deal.

I do think Konecny can probably still be a value in two or three years. I think the turnaround can be a bit quicker, I don’t think it will be four or five years for Philly, I think it’s two to three, so I can still see a window there. But you’re exactly right, that conversation internally needs to be had because he’s right at the cusp of a player that’s going to be expendable if you want him to be down the road.

Seravalli: I think two to three years is dreaming in technicolour for the Philadelphia Flyers. I think they’ve got a long, long way to go.

One word answer, keep or trade Carter Hart?

McKenna: Keep him. You build around him. I don’t trade him.