Leafs wouldn't retain unless it was an ELC without bonuses coming back.

I haven’t seen a more unbalanced trade since the Travis Dermott for Matt Roy trade proposals. There is no reason for the isles to this when the leafs have minimal cap space and leverage. It also doesn’t make sense from an age perspective.

Nylander at 5 million would be the best contract in the league. Leafs will never do this. But Nylander for Dobson one for one is a good trade.

Don't like it for Leafs. They need to get better, and imo this doesn't help in that regard.

No good reason for the Leafs to do this, Nylander is worth more

Disagree. I think this would be hard for the Isles to agree to. If the Leafs don't want to pay Nylander $10M (which they should absolutely NOT do) he doesn't have much value to them. Dobson I think would be a great fit on the Leafs. The type of player they need. Timmons goes to NYI just to fill out the D for the Isles but doesn't really matter. Nylander retained evens out the cap for this season and increases the value for the Isles to help get them to part with a great young D.
As for the Isles side, having Barzal and Nylander for the next 6-8 years would be dynamite! Those two would make magic.