This is a pretty daring move for the Leafs to pull off. Sure! we would be losing Nylander, but it would give Marner the opportunity to jump onto a line with Matthews long-term. And with the signing of Tavares, that second line still looks dangerous. More importantly, you've addressed the need for a defensive upgrade with a very cap friendly contract in Dumba.

You've also opened the door for other potential trades (i.e. Gardiner) come the US Thanksgiving and/or trade deadline should the need arise. I do however think that McElhinney will be moved before the season starts to avoid waiver issues with Sparks & Picard. And at the rate, the Marlies are going I would not like to lose those two anytime soon.

Interesting

Two things here.

1) Tavares at that price is an anchor. It would force TO to give Matthews 12+ next year and also Tavares will not be worth that much money in 2 years. If TO needs to approach JT the following way, "The Leafs will give you less than 9 mill a season for 7 years. However, you'll have all sorts of endorsement opportunities and you won't have the pressure of carrying the team since our young core will do a lot of heavy lifting. Also we have Babcock." Then Tavares will be affordable for the long haul.

2) I do not like the Nylander trade for 2 reasons. Nylander is the best player in that deal by a wide margin, this trade is a massive over payment to fix a hole that could be patched for far less as we wait for Liljegren to be NHL ready (He's as good if not better than Dumba)

What I suggest instead of the Nylander trade is either a smaller deal with Winnipeg for Myers (The Jets have a tonne of cap issues approaching so they need to clear space) Or trade for Chris Tanev in Vancouver.

Either of those trades would come at a huge discount compared to your trade and it also allows the Leafs to move Gardiner for anything really.