Matthews gets more than that

The Nylander trade will prove to be super tricky. His list is only ten teams, so that won't cause too much of an issue, but I think the biggest hurdle will be cap space. Unless Treliving, or the team he's traded to, pulls something similar do what Dubas did in the EK trade, TOR may have to take a contract back and not necessarily a desirable one.

A team that has no reported interest, but could possibly be a good fit to me is Seattle. Seattle has some players they could move that COULD be a nice fit, but also, if you're getting a quality player in return, it will affect the futures tacked on. Obviously a quality player coming to TOR may mean no top prospect or 1st rounder.

I think a Burakovsky swap could make some sense and in a trade like that, you'd probably squeeze a 2nd out of it, too which I think would be fair.

Now, you could also take back a rental like Eberle or Wenneberg which means you could probably get a some better futures back, too.

There is 0% chance AM34 doesn’t get the max term and someone will 100% give it to him

Most likely scenario Nylander. He remains a Leaf all season (just like the other Leafs upcoming UFAs). As a UFA, likely he signs with a non Leaf team as there are 31 other teams that can bid for services.
Leafs spend the cap they have allotted for Nylander on other player(s). Really it's not difficult to understand.

Leafs keep Nylander and who knows what happens when the Playoffs are over? They're trying to win a Cup and nothing they get in a potential Nylander trade will be as valuable as keeping Nylander.

GM's value him as a rental. So you won't get fair value. Only lowball Dollar store offers. It's not worth it for the Leafs.

Of course someone would give it to him, and the Leafs themselves would. But by all indications he doesn’t want the max term.

There ya go.

This is absolutely a possibility but I still lean to - ever so slightly - him signing an extension with the Leafs between $9-10M, 8 yr term. Matthew’s deal seems about right… 4-5 x $13M. Toronto is one of , if not, the top franchises in the league. Biggest fanbase, first class facilities and support staff, rich owners, significant marketing opportunities off ice and legend status awaits cup winners. I think we keep them both

But it still a cap league no matter how rich MLSE is. Is Nylander worth 9 to 10m? Seems like we're getting into Dubas territory overpaying for your players...or "hometown premium"

Not too many wingers , check that forwards, drive offense better than him & he’s a zone entry with control machine; defensively he needs to improve but offense is the hardest thing to generate. JT coming off the books soon so paying 3 guys $10M+ to drive offense at elite, elite levels works for me.