If you add Niemela to the deal (like the description says) and lower the cap hit retention to maybe 3-4mil (maybe throw in another pick for a 3rd team to retain), and SJ/TOR confirm that Nylander would resign with SJ to a long-term deal for 9mil or so, Sharks accept and it makes sense too.

A wild card here is the fact that Patty's helping Grier in the GM role, that Marner and Patty are father and son, that Marner has a super large cap hit like EK65, and so I think Marner to SJ is a possibility not many are discussing in a potential EK65 deal with all the focus on Nylander.

if Toronto wanted Meier and didnt want to include Nylander in the Package, how would they include him for goddam EK65?

HELL NO. WE DONT NEED 3 GUYS THAT DONT KNOW HOW TO PLAY DEFENSE! I thought the Klingberg was a stupid add bc it reminds me of the barrie and Rielly and we know that didn’t work. Teams that win the cup have a big and physical Dcore.

Could be, but Nylander just makes more sense to me, personally. He has less of a connection to Toronto than Marner, so I just assume Marner would be the one to stay put, but I guess they're interchangeable in this scenario.

Karlsson would be a better fit in Toronto than Meier would.

I would agree, but that's why you keep Brodie on the team and pair him with Klingberg, and move McCabe up to the 1st pair with Rielly.
I don't particularly like keeping Giordano as a full time skater due to his speed, but I really like the thought of these lines.

Buffalo obviously doesn't do that

2 very important arguments here:

1. If Nylander signs long term for $9m aav then it’s in Toronto. That’s right around where they’re hoping to get him so they wouldn’t trade him knowing that he’s sign for it.

2. Let’s say Nylander doesn’t want to be in Toronto and would sign $9m long term in San Jose instead.. that’s worth a hell of a lot more than Karlsson at $4m retained. At that point Toronto isn’t adding Niemela, or picks. San Jose is the team adding significant assets to make the deal happen.

What if Toronto added another 3rd and Niemela? Could swap Mittelstadt out for Krebs as well, but Krebs is worth more and has 2 years left.

Why would we trade either to Toronto? No thanks

brodie was TERRIBLE in the playoffs. He was our best dman in the reg.szn but terrible w turnovers in our ozone and middle of the zone. Idk if I can trust him 1st pair w rielly bc Rielly’s best games are when we had Hainsey and Schenn and when we’ve seen Rielly w Brodie he hasn’t or the pair doesn’t work.

Alright. I'm sure we can find an out-of-division team to trade those pieces to for similar production.

True, but I feel like having to babysit Klingberg might make him feel more responsible defensively.

I just don’t know why we didn’t resign Gustafson for 800K and save 4M. More points than Klingberg (yes also played w a crap Duck team) but also Gust wasn’t as bad as klingberg on defense

Your second point seems way off to me here. If Nylander doesn’t want to sign in Toronto, they are not dealing from a position of strength. In that case, that’s definitely not worth way more than Karlsson with 4m retained. And the Sharks in no way would trade for Nylander if he didn’t come with an extension, they are not close to competitive now, and so would be dealing Karlsson for young players/futures.

Actually Toronto would gain leverage in that situation. Their leverage comes from knowing that Nylander would sign an extension as part of the deal, negating the risk of San Jose losing him to free agency. Making him a very valuable asset and much more valuable than Karlsson.

Any Nylander trade would be similar to a Tkachuk trade - Leafs would be looking at getting roster players back to fill multiple needs and not picks and prospects

Buffalo is in a win now mode nearly as much as the Leafs.
But, Casey could be available if one of their prospects is ready to step in or if they could sign a UAF forward to step into the Sabres line up.
While Casey had a career season he was OK the previous two seasons with 41 pts over a 81 game stretch.
Unfortunately Lafferty, Robertson, and a third are not equal to Casey.
Lafferty would not break into the line up even after Casey was removed.
Buffalo does not need to add another forward prospect as Robertson.
He has decent AHL production but has not demonstrated NHL skills thus far.
For example Jack Quinn is the same age yet has already established himself.

Niemela and a third would be nice additions, in reality Buffalo would prefer Niemela and an asset equal to Lafferty, Robertson and two thirds.
Instead of 5 pieces, just two.

Respectfully, I'll be taking this hypothetical offer to another team because we don't have what you want.
I also wouldn't say Buffalo is in win-now mode as much as the Leafs. Their window is just starting. Leafs have 1 year left with two of the core, and 2 years left with the other 2. Half of the Sabres stars are still signed through the 2026-27 season, and have a lot more cap space available for when the others need to resign.