This trade doesn't make any sense for the Leafs. Kane wont resign in Toronto and they lose a lot of talent and potential prospects

Doesn't make sense for Toronto for Chicago possibly. Chicago could then flip Reilly and Nylander for mire assets.

Chicago might do it then flip Reilly and Nylander for additional assets.

Doesn't make any sense for Toronto though.

Reilly isn't the problem in Toronto he's the Leafs best defenseman. Sure the team needs more grit but trading your best defenseman for a tougher less skilled player isn't the way to fix that. Kane would certainly be a skill upgrade but doesn't address the grit/toughness issues. Domi would definitely add toughness to the Leafs but Nylander isn't the forward to move. Ideally that'd be Tavares, the only problem is he has a full NMC. That just leaves Marner who doesn't have any trade protection now but has a full NMC of his own that kicks in next year.

This trade doesnt make sense for the hawks either. They are rebuilding and want draft picks, not players

Depends on what Chicago thinks they can flip Nylander and Reilly for.

Both of them could be easily trade back to any team and get good asset in return. The fact they have signed contract give hawks time to flipped them .