This is really interesting and I wouldn't hate it if it happened, but I feel like CHI isn't quite at the point where it wants to make an expensive long term commitment to any veterans.

Lol

Wayyyyyy too little for Nylander

I'm with you. The best bet is for the Leafs to trade him at the TDL if they're looking to maximize trade value OR just let him walk if they're trying to win the cup. He's a good player, but I've got serious effort concerns with him. The Leafs are in a tough spot with Nylander and it's not the first time either. He's held out once...I don't see any acquiring team reaching a deal (on a new contract) unless it's a premium such that Nylander won't test the UFA market...to which then I'm just a pass anyway. Even though the Hawks have tons of cap space. It's not there to waste unless it's a premium for Matthews.

Hawks decline easily. Nylander has to come with an extension, Murray is a cap dump, you give up the 25’ 1st and you could possibly get a 1st for Raddysh at this TDL if he plays the season with Bedard and Hall. Terrible value.