You're losing a lot of production. Kane post hip resurfacing surgery won't be putting up what Nylander does right now. I doubt Jones waives his NMC considering it was between Chicago and Dallas to acquire him.

Even if Kane does put up the same or more, for how long? Every player going to the Leafs is also older than Nylander except for Raddysh who is the same age as Liljegren. So, really they would be shrinking their contention window a ton. Obviously, CHI isn't the team to be giving up young players for Nylander but if the Leafs aren't at least getting some younger pieces, it's definitely not worth it. I know Murphy and Jones are younger than Jarnkrok and Brodie but that doesn't change much for me as one guy is a ufa and the other depth.

Not a lot in my opinion. Let's not forget last year was the first year in almost a decade that he dipped below a PPG, the same year Nylander finally hit a PPG. Kane had 45 points in 54 games on an awful roster, with a bum hip. He got the surgery and took the time to recover to improve his injury, and he has some of the best doctors in the world around him. Sure, Nylander may outproduce him, but Jones should also massively outproduce Lily. Regardless, the slight dip would be worth it to address our greatest concern right now, that being a D core that is bottom 10 in GA/G and PK%. This always addresses our D longer term, and allows us to save our draft capital instead of spending it on bargain bin solutions to the top 4 at every TDL (Gio, Schenn, Lyubushkin, McCabe, etc.).

Defense matters, our defense core sucks, real bad....

I'm telling you right now, there's no way he does. Trades/signing don't make sense at all.

Nick Backstrom had the same procedure done and is likely retiring. It's a very, very difficult surgery to recover from, let alone regain the power to compete in the NHL again. It's not going to be easy for Kane.

You're making this team significantly older, which is a common theme of the leafs in real life. Sandin trade, you want to move Liljegren, what's next? Sometimes you just need to hold onto your pieces and let them come together. This roster has faced far too much turnover and the result is in their playoff success.

Hawks would never use up a retention slot for 7 years and Jones would never waive his nmc for a Canadian team.

Saying they don't make sense is a failure to understand, rather than a valid criticism...

I never said he would outscore him, you're missing the forest for the trees here. First off, Kane could fill the role Willy is in now and would still be likely to make that the best 2nd line in the league. The key thing to understand here is that Nylander is our most valuable asset that we can trade right now with the rest of the top 4 having no trades. Kane is a free asset, who would step in and allow us to trade for a boatload of value elsewhere, while still forming an elite, elite 2nd line.

So it's not just Nylander/Liljegren/Jarnkrok for Jones/Murphy/Raddysh, but Jones/Murphy/Raddysh AND Patrick Kane. This allows us to retain our draft assets and our best prospects while addressing the glaring holes in our backend. And not just addressing them for this year with TDL rentals, but with long term solutions that will allow us to continue saving those futures, with nothing much coming through our defensive pipeline.

Then you consider Kane is $2 mil cheaper this year, but probably more than $5 mil cheaper until he expires. When he does expire, that will leave cap space for RFA contracts of guys like Knies, Cowan, Minten, Woll, etc., contracts we would 100% not be able to complete all of with Willy on the books making 11 mil, as he exits his prime. And again, I know you're latching on to this to further your narrative, but did Matthews somehow get worse after his wrist surgery or did he score 60 goals? I thought surgery was repairing the injury, not creating one...

As I said above, this would leave us with a top 3 forward group and arguably a top 3 defensive group, and a roster that is built for the postseason when checking gets tighter. This team is so much better than what we're icing now it's not even funny, and would quite literally make us cup favourites. Not to mention all the extra high end picks we'd be giving our elite scouting staff.

Wrong!

I don't doubt it, I'm just saying there's no justification for it even if he does. Makes more sense to lose Nylander in FA than trading him for a return like this as long as 1) they have a chance at winning the cup and/or 2) there's a possibility that he might re-sign. Reinhart, Stamkos, or even Kane (if he proves that the surgery was successful) might all be available to sign as Nylander replacements in free agency.

There's no justification even if he does? How do you see this as in anyway logical? Your last point is irrelevant to the most important factor in all of this, which is getting value back for an asset that will help the team now and in the future, so long as we're able to maintain a competitive forward group, which I have.