There is no rational case to trade one of the Leafs' top players because somehow that magically makes the team better. It is extremely hard to make a team better trading elite or near-elite talent in the immediate term, even if you're happy with short term gains.

The famous Matthew Tkachuk trade is one that many people want Brad Treliving to repeat with the Leafs – to rush one of those bums who keep losing out the door. You don't get Tkachuk in a Leafs version of that trade. You don't get the best player; you get two old players on expiring deals that present you with cap complications if you re-sign them.

Cap complications is the only case for trading a member of the core, and there's only one person who can and should be traded for this reason.

As of time of writing the 2023-2024 cap is projected to be $83.5 million, but might be higher. The 2024-2025 cap is projected to be (by the NHL) $87.5 million with the following year at $92 million. I think the cap will top $90 million before 2025, but that's speculation, and those conservative projections will do as context for now. There will be more cap space, but it will disappear quickly.

I already discussed what I think an extension for Auston Matthews will look like, so this is really part II of that theorizing.

Auston Matthews needs a new contract
Count me out of the group that thinks the Auston Matthews contract just totally must be signed by July 1 or the sky will fall. There is no plausible threat of a trade to hold over his head because Auston Matthews can’t have more leverage than he has just by virtue of who he is.
PPP LeafsCathy Squires

Huh, that picture still works, too.

Let's go top end, and say Matthews signs for $15 million or about 17% of the cap as it will be when his extension takes effect. The Maple Leafs have eight players currently under contract for that season – NHL regulars that is. So it's impossible to really discuss how the rest of the roster will look and what it will cost but upward pressure on all salaries is to be expected. Not having many players locked up to term deals gives the team flexibility now, but will add to the cost of replacements.

There are three significant contracts: Morgan Rielly at $7.5 million, John Tavares at $11 million in the final year of his deal, and Mitch Marner at $10.903 million in the final year of his deal.

There is a lot of assuming going on right now, in the media and fandom, that the Leafs will either trade William Nylander or let him walk when his contract expires next summer because the raises to Matthews and Marner will make it impossible to pay him too. I think that's wrong, and it's not what the team will do. But that's getting ahead of the story.

Let's ask ourselves this question: If Matthews signs this summer, what happens next?

Next up is Nylander who needs an extension before the start of the 2024 season. But the next thorny issue is actually Mitch Marner. Here's how his first major contract negotiation went, one so very often used to accuse Kyle Dubas of a lack of manly fortitude:

M: I want the Matthews' deal

D: We want you, we love you little Mitch, we think you're a bi-

M: I want the Matthews' deal

D: We're willing to go term here on a reasonable AA-

M: I want the Matthews' deal

D: You're a great support player to Matthews and we wa-

M: I want the Matthews' deal

D: Look, you're not even the best winger in the NHL, you can't ex-

M: I want the Matthews' deal

And so on through every possible counter argument, presentation of charts, graphs, pleading, tears, anger, manly declarative sentences said with unearned confidence, and all the rest of the things people have thought up until, at nearly the last minute he could be fit under the cap, Marner condescended to sign for a small discount and got something so similar to the Matthews deal, you might call them the same.

BTW, I offered to roleplay this on BtoE several times, and they just would never take me up on it... strange. Anyhow.

What makes anyone think he's not doing exactly the same thing again?

The most logical scenario if that's the case is the the Leafs will play him through this season and visit the idea of one last try to get him to take a reasonable deal early next offseason. If the answer is no, the blockbuster deal happens next summer.

Then the Leafs can re-sign William Nylander to another marriage-ceremony contract of seven or eight years at an AAV that will be a bargain within a year. $9 million maybe $10.

Just one problem with that neat little story. Mitch Marner has a no-move clause in his contract that takes effect... tick, tick, tick... on July 1 of this year.

So what do you do if you're Treliving? While it's true Dubas was ejected from the Leafs leaving behind a pretty clean slate and no big messes, he did have this one ticking time bomb in his desk drawer. Do you set it off now, and just go for it? Trade Marner for the best combination of winger and defender you can get and build around that starting with the Nylander extension?

Do you wait a year and think you can get him to waive that no-move for you? He's been so, so accommodating on contract issues in the past, you know, I think he— ha ha ha, as if!

The choice is this: trade him now, or else in a year you can either re-sign him for a massive amount or let him play out the season and walk for nothing. Does Treliving want another Tkachuk, a Huberdeau or a Gaudreau? He gets to pick. And the decision gets made now.