Tomorrow we’re treated to the end of year press conference from Dubas, Keefe, and Shanahan. As a bit of an appetizer, tonight we have Elliotte Friedman breaking down the Leafs heading into their extended off season. Of course we have some thoughts on his thoughts too. You can find Friedman’s full article here.

I think GM Kyle Dubas’s plan was to give Toronto’s “Big Four” (Mitch Marner, Auston Matthews, William Nylander, John Tavares) one more season, no matter what happened in this year’s playoffs.

But, as Mike Tyson once said, “Everyone has a plan until you get punched in the face.”

Right off the start we are treated to an important reminder that Kyle Dubas has no interest in breaking up the core of the Leafs offense. For the most part it’s hard to disagree with moving on from any of these players, and especially to do so in order to address defensive needs. There are other options. That said, there’s a lot of money tied to those players, and a bit of cap flexibility could do wonders.

The Maple Leafs have more flexibility than some realize. Nylander’s actual cash payments drop below his cap hit the next four seasons, Kasperi Kapanen’s for the next two. (My understanding of the post-signing no-trade promise to Nylander was that it was intended to be solely in the immediate aftermath of the agreement.) In 2021–22, Andreas Johnsson and Alex Kerfoot join that list.

The bonus laden, front loaded contracts will certainly make the Leafs an attractive trade partner. Players like Marner, Nylander, Kapanen, and Kerfoot have all had their signing bonuses paid out, and could be good fits for cash poor, but cap space rich teams. How they pay the player beyond this year may be an issue, but for a lot of them they also see substantial pay drops next season as well. The Leafs are in a very different position than last summer when Toronto had to pay to get players taken away. Selling high is the name of the game. Listen on everyone, but sell on the ones that makes sense.

There’s a Frederik Andersen decision due, too. He’s one year from unrestricted free agency, and there are several uncertain goaltending situations — Chicago, Edmonton, Minnesota, Pittsburgh, Vancouver, Washington among them.

I’m sure you’ll read a lot more on this site about keeping or moving on from Andersen in the coming months, but both Chicago and Edmonton seem like they will be aggressive in finding a number one goaltender for next season, and perhaps Andersen is the best fit. Both teams make sense from a trade partner standpoint as well. The past two years seem to be plagued with Oilers trade rumours.

I can’t see him entirely changing his belief that Toronto should play a certain way, but I can see him modifying it. Someone else with some bite is coming, and I’d guess it’s on the blue line. (Mark Borowiecki? Radko Gudas? Who knows.)

I am someone who has firmly been on Team Gudas for a while and it would be great to the Leafs finally bring him in. Gudas has enough ability to keep up with the game, but also brings in the element of being able to put opposing players through the glass, something that has been missing from Toronto’s blueline for a long time. His career to date isn’t Komisarek-esque, but there is always a worry he’ll end up that way as he ages. Gudas would be much more of a Danil Markov type player, and it’s hard not to like that.

At some point in the next couple of weeks, there will be a conversation with Jason Spezza…

It’s hard to say where this goes, but the Leafs thought he had enormous impact on their young players and went above and beyond to be a positive influence.

An affordable Jason Spezza returning seems like a no brainer, especially if there is going to be some turnover. A stable presence like Spezza can be calming and there’s no doubt he can still play well enough to be a solid fourth line contributor, who can step up to the third line when needed.

It may depend on what happens with Spezza, because I don’t know if you can have both of them, but I think Joe Thornton will be on Toronto’s radar, too.

Personally I wouldn’t object to having both, but again it depends on what happens with the rest of the roster and what they’ll cost. It’s hard not to love Joe Thornton, and seeing him in a Leafs uniform, even in the twilight of his career has a ton of appeal.

The Maple Leafs have an opening on their coaching staff, as power play specialist Paul McFarland heads to OHL Kingston. Out-of-the-box thought: Bruce Boudreau. He will want to be a head coach, first and foremost. That’s what he is. However, he’s always had a fascination with the team he grew up watching and played for.

This sounds like a dream, but would require a ton of buy-in from Sheldon Keefe to have an experienced (and arguably better) Head Coach with him behind the bench. It could never work as a long term relationship, but Boudreau is a great fit for the offensive driven Leafs.

Looking at those Toronto wingers, I wondered if Edmonton is a fit. Leon Draisaitl and Connor McDavid need help. The Maple Leafs and Oilers have been close on some things before.

Like we said with Andersen, these teams get rumoured together a lot. It seems inevitable that the Leafs and Oilers hook up on something. As strange as it seems, the Oilers have some quality defensemen available who could be a good fit with the Leafs.

Finally, on the Florida GM search situation…

I think Chris Drury is high on Florida’s list, but I’m not convinced it’s a fit. You’re also going to hear Scott Mellanby, Laurence Gilman, Michael Futa and more.

Laurence Gilman seems like he’ll be a hot commodity this offseason, and that puts the Leafs in a very interesting situation as well. I still think Gilman goes to Arizona, but that Florida could be looking at him as well speaks to the need to find the next best fit as Assistant GM.

Tomorrow’s press conference should begin filling in some of the blanks on what the Leafs are thinking going forward. And while it may feel like a long two months before any real action is taken, the work behind the scenes hopefully started two days ago if not earlier.