Can't see why Toronto would do this.

If for some reason the Leafs made this terrible trade the Jets should retain half on Matthews and ship him out for the best/most they could get.

Again though Toronto wouldn't do this.

As a leafs fan, I think the jets make the best sense for a trade partner. This deal is totally not going to happen from the leafs perspective. Put yourself in the shoes of leafs management and think why they would do that. For one, goalies don’t have much value in the market. 2, the leafs have Samsonov as an RFA. They could extend him for multiple years at a reasonable AAV. Hellebuyck is the better goalie but not for that value. He’s gonna want crazy money after this year. Leafs don’t want him in my opinion. I’d work something around ehlers and scheifele

Auston Matthews > Hellebuyck+Scheifele.

If Winnipeg trades Hellebuyck and Scheifele they're heading for a rebuild here. So why would Chevy pay Matthews 8 x $15,000,000 when rebuilding? I mean come on man. Trade is bad for both parties.

Toronto shouldn’t and wouldn’t do this trade, Winnipeg doesn’t make sense as a trade partner for any of Matthews, Marner, or Nylander. All of those guys would leave Winnipeg as soon as their contracts are up.

Winnipeg and Toronto don't line up well for a big trade at all.

Toronto has dealt a lot of picks and don't have many interesting prospects, player swaps like whats suggested here don't really make sense for either side.

Not enough coming from Winnipeg. Also, how do you get Matthew’s to sign or accept a trade to Winnipeg? They are having trouble keeping their own players.