Buffalo has no need for Bailey and no need to help out struggling conference rivals

The Leafs are trying to win now, which means the picks and prospects don't hold as much value as they would to another team. This trade makes the Leafs worse now, which is the opposite of what they are trying to do. On paper the value is not far off, but the Leafs are not a good trade partner for this situation.

If the leafs wanted to spend 5M on a goalie they would give it to Campbell, only way I see them move Nylander to the islanders is for either Wahlstrom and a first or sorokin

Interesting.. I would be willing to move a 1 + Wally for Nylander

Here's a deal I think could happen:

Leafs Get:
Josh Bailey (1 mil retained)
Oliver Wahlstrom
Bode Wilde
2023 1st (top 10 protected)

NYI Get:
William Nylander
Joseph Duszak
2023 3rd

Been hearing a lot that Bailey wants to come to the Leafs as him and JT are close friends, and Bailey is the kind of player the Leafs need. This gives the Leafs value both now and in the future, which is what would be needed for them to make this kind of deal. I think that deal would go through.

Between adding Wilde and Bailey (specifically the mil retained) feels like alot but framework is solid imo

The million retained was simply to make the cap work for the Leafs. That could easily be removed from the deal if they decide to trade away either Kerfoot or Holl.

I’d rather move willy in a package for saros. We get a better younger goalie even though we have to pay more.

Nashville won't be moving on from Saros, askarov is about 2-3 years away from being starter ready

I don't think the laefs have an interest in Bailey. I think the point of going for Wahlstrom and the first is value and cap relief to sign a goalie, I mean I understand some sort of cap hit would have to be heading the leafs way but I don't think going from Nylander @ 7 to Bailey @ 4 is worth the cap savings. Would have to be something a bit different.