Quoting: SweetRevenge19
Pittsburgh sheds a ton of salary to retool with and gets back nearly what they gave up in the trade, why wouldn’t they do it? I think Karlsson would be a great fit on the wings as good pairing with Edvinsson and mentor as well, while an upgrade over Ghost on PP. Not that worried about the contract as Karlsson, Copp, Cat, Stamkos, Gibson, Seider, and Raymond all have the same expiring term and Maata, Petry, Walman, and Abdelkader would already be off the books. I disagree with everyone on here overpaying Seider and Raymond with 8 year $7/8 million deals and dismiss all those ACGM. These two contracts are a lot closer to what they actually will get just you wait and see. Maybe they get a little more I’ll concede, but anyone who has paid attention to Yzerman’s GM career knows he does bridge deals and is stubborn as hell on $ amount to young players. Sergachev got $4.8x3 before getting $8.5x8 for example. Kucherov got 4.76x3 before getting $9.5x8. We’re not Buffalo or Ottawa, these guys aren’t going anywhere.
I don't disagree with your assessment on the Yzerman contracts, Point is another one and even the Debrincat contact is proof of that. That said, I feel this team would be much better locking these guys up long term and maybe sacrificing the next season or two in order to be alot more competitive in years prior. You can look at those deals and say pretty easily that it's what Yzerman does. My argument is that it was a different time, more flat cap, and a different team, a legitimate Stanley Cup contender who almost had a 3-peat. There might have been a desire for these guys to take slight discounts to stay together. I would look at Brayden Point's bridge as a better comparable for Raymond. Also take into account the percentage of the cap the deal takes. Raymond, if compared to Kucherov would need 5.7M to be a similar contract. Brayden Point would be 7M. I used comparables of Boldy, Caufield, Cozens and Svechnikov for Raymond and Heiskenen and Power for Seider. I guess it all determines in which way you want the team to go, get a bit better for the short term but possibly lose out in the long term of those guys grow beyond what they could be signed for long term. Or sacrifice a bit in the short term in hopes that those long term deals will provide great value in the long run.
As for Karlsson, I personally feel like I would rather Edvinsson partner with a more defensively responsible player instead of trying to have to cover for him all the time. I think that would help him grow his game a bit more, which I believe is a bit more of a two way style, than force him to make defensive plays he probably isn't ready for. I would look at Roy, Pesce or Tanev as guys I would want him to be partnered with. I could see the desire for Simon though, Karlsson was probably a hero for him growing up.
No idea what will happen with Stamkos but I do know that he would get the same money after taxes in Tampa if he signed for 7M. I could see him taking a bit of a discount to stay in Tampa.
Also to note, Yzerman didn't sign Sergachev, he was already in Detroit when that deal was signed.