If Van is in a playoff spot and they work out a reasonable extension I'd do it (minus Kampf though)

Why is Nylander different that the other Leaf upcoming UFAs? Or the hundred of other NHL UFAs. They all don't get traded
Why would the Canucks want to give up a first rounderfor an upcoming UFA? Nylander's and Kampf's M NTC likely nix the trade

Because he’s William Nylander

Nahh Kampf needs to be in the deal. It’s between him and Reaves. Both Deals gave by Treliving

The thing is, if the Leafs are in a playoff spot they aren't going to allow a star player to negotiate with another team.

As a have said before.....can't think of a reasonable trade, add the totally impractical extension.

The Leafs aren’t going to let him walk for free 4 months later if he doesn’t resign by the tdl. They’re going to trade him for a good return that will allow them to stay competitive and pick up future assets. Everyone has their own opinion, but for me Nylander is a 10M player. Not every team can afford him at that cost. Probably not the Leafs. With Matthews who is probably going to earn around 14M ( witch is mind blowing knowing he didn’t win a single 2 round playoff game and he didn’t win a cup) You give this type of money for players that proved things in the playoffs. Wish he took a discount like MacKinnon did at 6.9M. He won a cup then he signed that 12.6M$ deal. Now back to Willy, why would he take a discount when Marner Tavares Matthews are all making 11M+. Plus it seems like he’s the only one showing up in the big moments.

No reason for VAN to make that trade.

Wdym if Nylander signs a reasonable deal then it’s worth it.
Pearson is already probably going to leave next year.

Well that ain't true. Now the Leafs might trade Nylander (or any player) if it helps them win THIS seasons. But why did you trade just Nylander....why not Matthews, Bertuzzi, Domi, Lafferty, Brodie, Giordano, Klingberg and Samsonov. They are all upcoming UFAs. Sorry, Cup contending teams don't trade upcoming UFAs....just because they are upcoming UFAs. Actually contending teams actually acquire upcoming UFAs for a Cup run without any hope of resigning them.

I don't expect Willy to take a discount....so what. He signed for an appropriate contract at the time. After Nylander was signed, Dubas overpaid Matthews and Marner on their RFA contracts. The Leafs have 43m free next summer if they don't sign their UFAs. Why worry. Leafs will likely sign a few of their own, and a bunch of other teams UFAs.
Just an exchange of players and cap.

Because we already know that Matthews is going to sign a new deal. If Lafferty Brodie Gio Klingberg leave for nothing it’s not a big deal comparing to Nylander leaving on free. Dubas overpayed Matthews and Marner on their RFA contracts but now Treliving can’t make the same mistake to overpay these two. They need to set a salary cap structure. I will take the Habs as an exemple for this, Suzuki Signed 8X7.875M two years ago. This year Caufield deal was expiring, Hughes set that cap hierarchy. No one is making more than the Captain. Caufield then signed to a 8X7.85M. Just a little bit less than Suzuki. By giving Matthews 14M, Treliving is going to do the same mistake that Dubas did, nothing is going to change, IF Matthews signs that 14M deal, Marner is going to ask for the same money. 28M for these two players. You only give this type of money to players like McDavid Draisaitl and MacKinnon.

Trevling may not be the guy you want negotiating contracts. Huberdeau's new contract 10.5m X 8 years is the second highest paid LWer and starts when he age 30. Kadri at 7m X 7 years started when he was almost 32. Dubas was horrid in contract negotiations. I don't how Dubas and Trevling got GMs jobs after their previous GM tenure.

If I was Shanahan, the guy i would have hired to be the GM would be Darche. Add Bergevin if you want more experience. I feel like they should have kept Dubas but he wasn’t the problem. Apparently Shanahan was blocking trades. Dubas didn’t have the full Power. And for Treliving, we already saw the he is awful on contracts negotiations, Gave Kampf 4X2.4 and Reaves 3X1.35. I dont expect the Leafs to win a cup in the next 5 years sadly. So much Talent and Potential wasted.

If Nylander is traded before the season starts, Leafs aren't going to get what any Leafs fan thinks he is really worth.
If Nylander isn't traded before the season starts, and the Leafs look like a playoff team, he'll get traded before the draft with an extension rather than letting him go for free. Cost will be pennys to the dollar.
If the Leafs aren't a playoff team trading at the deadline is going to be the easiest way to get what his real value may be since every team overpays there.

Every Leafs think they can get Tkachuk return.

And maybe they can, but probably not with their current GM. Looking at comparable player like Gaudreau, Nylander's camp is going to have to realize the 10M+ contract may not be out there.

I'd let Willy play the season. He climbed over players to get his 40th. Imagine what he'll do to justify 10.5. No Reason Leafs couldn't match, if Willy says no, he was never going to say yes. Dump the silly clauses.