1. Declined by both
2. Anaheim declines
3. Detroit declines
4. Detroit declines

This would cause the rebuild to be extend by multiple years.

Karlsson isn't waiving for Detroit. Chiarot will require at least a 1st attached to move. Horrible signing by Yzerman.

none of this is even remotely likely or realistic

No he won't and no it wasn't. With the market that was available, warts and all, Chiarot is *fine*.

People MASSIVELY overreact to his contract and act like it was 8x10. Realistically, it should have been 1m less per and 1 year less. Is it ideal? No, not by any means, but it's fine.

He still adds some badly needed heaviness on the back end, can skate well and has some sneaky offensive ability. He just needs to be insulated by a stay at home partner, that can read when he goes roaming. After the deadline last season when he was paired with Maata, he was pretty good actually and that was when he was flipped around to his off hand.

Don't get me wrong. I'd like him replaced, but not at the cost of paying to move him. It just doesn't make any sense.

The cap is going to rise by 4m+ after this season on top of multiple large contracts falling off the books. They are looking at 40m+ in cap space in 2024-2025 without these trades.
You sign Seider to a 8x8, Raymond to a bridge deal in the 4x6 range, Rasmussen at 4x4, Bergeren 4x4, and lock up Scheifele to a 4x6. This is with them all demanding top dollar. You could 100% make this roster work next year and it would get better every year with the cap rising. Eventually Kasper, Danielson, and Axel Sandin Pellikka would join the group as well at some point. If you get the guys in RFA to settle for a more team friendly deals you would have a ton more options in the 2024 FA as well.

I actually think Chiarot would get claimed on Waivers if exposed. Chicago and Anaheim are trying to get physical to protect their stars and both of them need multiple players on the back end.

Just the players you targetted in your trades. Neither of them play good defense. Both over 30 years old and will decline. Does this team make the playoffs? Maybe. But the fact you traded away really good young pieces for guys that are likely only going to decline isn't really that ideal. Also you have the most expensive fourth line in hockey. Why get older just to try and push for the playoffs for a year or two only to take a step back in 3-4?

I don't think San Jose would turn down that deal. They get a high end defensive prospect, a veteran defenseman, a 1st round pick and a 3rd round pick right when they enter a full rebuild.

No chance. None. This offseason has proven more cap restricted than any other. The volume of trades is the lowest it has ever been.

San Jose wouldn't. Karlsson would.

Detroit wouldn't even consider that trade in the 1st place

Personally, I like the idea of a Chiarot-Holl 3rd pair

I think it's going to surprise a lot of people. I think they're going to cover each other's deficiencies surprisingly well. Chiarot's biggest issue, is that he roams and Holl is a stay at home defenseman, so as long as Holl can read when Chiarot goes Leroy Jenkins, that will be huge to insulate Chiarot from that issue. Holl, on the other hand, is big, but soft as cotton, so being paired with Chiarot should cover that up and maybe make him "play a little bigger" (I know, silly that a 6'3" dman needs that) having that protection.

It could also be an absolute disaster, but I am cautiously optimistic they're both going to surprise everyone.

Winnipeg would be looking for quality, not quantity.