Why is TO paying more? Nylander and Connor is a wash and Brodie is better than Dillon by a large margin.

Bad idea for WPG and this seems like a lateral move for the Leafs that could backfire.

Nylander has 1-year vs Connor's 3, Hirvonen is a good prospect but not that significant.

And? Both teams would be resigning the respective players long term in this sort of swap. Otherwise why would Winnipeg do this?

Because they get better

Well this isn't a really good idea for the Jets.
Connor has 3 years left and Nylander is 1 year from UFA and would most likely demand more than Connors 7.15 per if he resigned.
Brodie is a soon to be UFA aswell with a cap hit that isn't very tempting, plus he is 33 years old, so it doesn't seem like they'd be looking towards the future at all on this one.

Don't see the leafs trading one of the big 4 for a non-physical forward. Leafs lack grit in the top 6, this is the only type of upgrade their looking for in the forward group. Would like to see Jarnkrok, Holmberg and Robertson gone, they need some more playoff style guys in those spots.

It's easy to say Nylander and Brodie resign but there likely isn't going to be a guarantee prior to the trade, for WPG.

A few things to consider:
1) WPG needs to literally find players who want to play in that city
2) if Connor is getting traded, that probably signals a rebuild or a forced retool because of core players wanting out.

Then find a way to fit Connor without moving nylander who you would likely keep as an own rental.

Better that the Leafs not make that trade at all imo. The top 6 should be fine. If they trade Brodie, then they should be acquiring a younger 6-7M guy (like Hanifin). They should lock Liljegren now for cheap at 4M, even if he ends up a 3rd pairing guy that's not going to be way overpriced. I would take Barbashev+budget player over Bunting+Bertuzzi.

Bunting probably doesn’t take much of a discount and seeks something slightly under 5M from Tor. Bertuzzi or Barbashev might cost them up to 6M.