This would be the trade, maybe there's a little something more to it but these 3 players make it happen

If the Isles would be willing to give up Dobson, I'd support moving Willie. But I still prefer to sign him long term at $9M

So...

Mathews- 13.5M?
jT - 11M (next contract -7M?)
Marner-10.6M (next -12M?)
Nylander-9M?


Thats alot of the pie...

JT's next contract will need to be less than $5M or the Leafs need to walk. He's made his $100M, start a family near home and play for his childhood team. (not to mention the ton of money he's made from endorsements because he's in Toronto). If he won't take less, let him go elsewhere.
Matthews probably won't sign full term at $13.5. Personally, If he's not willing to sign $13.5 x 8, give him $12.5 x 3 and let him earn his next contract.
Sign Mitch to the same thing or a little less. I'm fine with shorter term contracts, exp if the cap is going up as much as they say the next 3-5 years.

I really like the trade for the Leafs, Dobson still has a lot of upside and his bridge contract is good value.

But this would also put the Islanders about $3.0mm over the cap. I just don't see the Islanders doing it. +Nylander would need to agree to a reasonable extension ~$9.0 (max $9.5). I am not convinced he is going to be reasonable. As such, I think there is a low probability of success here.

I get the idea that he would be more reasonable with another team than the Leafs.

Love Willy but I’d do this deal in a heartbeat.
Any deal with NYI has to include one of their top 3 D men.
I’d see any team signing Willy to a long term deal 8 yrs will regret it. Willy at age 31 to 35 that’s four years he won’t be earning his salary imo hope I’m wrong though.