Would Kane waive for NSH? Maybe.

Would CHI trade Kane for Sissons' bad contract, a first round pick that can't be top 10, and some random bits and pieces? No, not unless NSH was literally the only team Kane agreed to go to.

both Hawks and Kane pass

I think Domi is a more likely target from CHI if NSH wants to trade with them

I'll disagree about Sissons being on a bad contract. I could see that as such from a CHI though. Presumably they're going to be in tank mode for the next couple seasons. Most vets they bring in to fill out the roster will likely be pending UFAs that are easier to move at the trade deadlines.

CHI probably could get a better return, but NSH shouldn't and (hopefully) wouldn't be interested in him anyway. I don't think the protection on the 1st matters much, as anyone picking up Kane at the deadline would have to be a stronger contender than NSH is this season. The team acquiring him isn't going to be potentially drafting in the top ten anyway.

But it does matter because it's not just anyone picking up Kane: the proposal is for Nashville to pick up Kane, and they are currently in position to draft 12th. You can calculate the strength of the pick in to the trade deal (it'll be perceived as much better than, say, the BOS #1 pick), but Davidson's not making this deal without a 2023 First so protection for the pick is not realistic.