Please explain why Toronto would give up their 3rd round pick for a 2nd (max a 20 spot improvement).
JVR for Kruger is horriable even with Schmatlz

It's a 6th not a 3rd. I think that that trade would benefit both teams, because the Leafs get a defensively styled forward in Kruger, and another depth playmaker in Schmaltz. It allows them to stay good while also tightening up a somewhat lacking defensive group (besides Kadri, they have hardly any two-way forwards). JVR fits well into the Hawks' style, and both teams do well.

Why would Toronto retain salary on a good contract...just to be nice and help out Chicago? Last thing leafs need is more forwards

Toronto would much prefer Alex DeBrincat and Chicagos first round. straight up for JVR

Chicago would like Reilly for a 7th

Dude; JVR is only a beauty contract for this season and next. Is a premier power forward in todays League. Debrincat is a solid prospect/2nd round pick. And Chicago's first rounder will probably be a 20-30th range. Its not that much of an ask.

Well, I don't think Debrincat is a solid prospect..He's a real wild card like Bracco. Schmaltz you would think has good possibility of being an NHLer....maybe in the Bozak mode.
The trade. If the Leafs loved Schmaltz it might be a fair deal. But one thing the Leaf don't need is another slight centre (Schmaltz) so if JVR is traded I don't think that is a fit for the Leafs for the Leafs. Kruger the Leafs don't need him...Matthews, Kadri, Gauthier for sure are Leafs centres next year, and if Bozak is around (and I think he is at the start of the season for sure) and maybe Nylander goes to centre. So again Kruger isn't a fit.
Ideal Leaf return for JVR...Kevin Bieska of eight years ago.

Regarding the Leafs one way forwards....that is hardly true. 6 rookies at forward, and 2 rookie Dmen has made the continuity difficult at times. But all the rookies are willing workers even defensively though Nylander seems to make lapses that the others. The Leafs look very organized defensively and rarely the goalie barraged with multiple shots off one rush. (unlike previous years) No these players don't cherry pick. One reason that I like Komarov and Bozak on the team is that those guys work at their defence also. I'm a Leaf fan but I think a neutral hockey observer, these guys work and like doing it. Maybe something like the the Hawks of 12? years ago, a lot of young guys brought together at the same time, and finally a coach that players will listen too.

Debrincat is the real deal. There are 3 players with mutiple 100 point+ seasons for the otters. Mcdavid, strome, Debrincat. His knock before the draft was he played with those two before...let's see him do it without them. Now he's having his best season yet. Personally, that goal scoring winger is needed more for the hawks than a center too. They've been searching for that LW replacement. Maybe Hartman sticks, but having arguably the best player in the OHL is pretty nice too.

I don't think the Leafs would retain that salary. Otherwise, you have some interesting ideas.