There's nothing in it for Winnipeg.

So 1yr of Nylander and Samsonov gets you Dillon and Hellebuyck?

Chicago can get Nylander to re-sign and play with Bedard.

I dont think they'd overpay when they can try to go out and get him for free the following year

If there's a Nylander trade there's most likely going to be a bidding war. He only has a 10 team no trade list, and any team that trades for him will have an extension ready. I don't think Treliving will walk him to free agency. Unlike Matthews and Marner he doesn't have full control of his destiny.

CHI declines.

Hawks decline. They'll value those 3 picks way more than one year of Nylander. And no, he won't resign in Chicago unless Hawks way overpay on his next deal. He'll be 28 next summer, 9 years into his NHL career. Nylander will want to play for a legit contender, not a team that's entering year 3 of what's probably a 5 or 6 year rebuild plan.

Leafs stars are mercenaries. They'll go to whoever pays the most and Chicago has a lot of cap space.

He would be an interesting add, if he would sign an extension... but just wait for FA, maybe get him for $8m x6?

Yeah. Maybe. But, like @Hawksguy81 said, he'll be 28 when his contract is up. Which means he will probably be on the wrong side of 30 by the time CHI is back in the playoffs in any serious capacity.

Ha. You made my point for me. Hawks will not want to overpay to resign him. If the Leafs do make Nylander available this summer, there will be multiple teams interested. Just not the Hawks

Can't see him signing for that to stay in Chicago. It would be year 3 or 4 of that deal before Hawks are even back in playoffs. He'll want big $'s to stay if he can't play for a cup in my opinion.