Holland isn't going to take Keith's full cat hit.

The fact that Caleb Jones is even a topic of conversation wrt this trade means that there will be retention. There is no world in which you give up assets for Keith. He was a great Dman and could be a great mentor but I can't help but think that is what coaches or trainers or staff is for. The mentors on the ice need to be good. Keith is no longer that and carries a significant cap hit. I could see Keith working for a team like Ottawa since the actually $$$ owed is quite low but Keith wants to be out West. Which again means you DONT give up ANY assets for him.

Oilers decline the Kieth trade, he’s not coming to Edmonton without major retention I’d like to see 50% but I don’t think the Hawks would do that
The only way he comes at full cap hit is if Neal goes the other way, 1 for 1
Hawks have one team to deal with and he 100% don’t need to make this trade, the Hawks either take a massive loss on this one and reward a guy that’s given everything to the organization or they decided to piss Kieth off balls in their court he aren’t doing then any favours here

forget keith oilers need a good goalie they could be cup contenders if they have one. i don't think mike smith is gonna you the cup.

I agree. Neal would have to go back in order to make this somewhat acceptable for the Oilers. But like you said Neal coming back wouldn't help the Hawks a single bit. They don't need forwards, they want to free up cap space and they want young boday. None of this applies to Neal. I think the Oilers should an will stay away from this and Keith will end up going to Seattle.

I believe Seattle has already send their not interested in Kieth and unless the boarder reopens Seattle’s not even a option for Kieth

Not really. Neal's buyout is $1.9M per year, if Chicago trades Keith for Neal and does a buyout they save about $3.62M in cap for the next 2 years. If they buyout Keith it saves them $1.5M next year and just $900k the year following. If Keith retires the Hawks would be on the hook for a $3.73 million recapture penalty for two years, so that's not a great option either with just $1.81M in cap savings.

https://www.nbcchicago.com/news/local/hossa-keith-deals-a-potential-cap-burden-for-blackhawks/68986/

I personally think Keith would be a great addition for the Oilers. A lot of people/reports are saying that he's still a good player, at least a great fit for the 3rd pairing with Bouchard. Add that to the fact that he's kind of a mentor like you said and I see him as a good option.
That being said, Holland has to play hardball here (which he apparently is and I like it). I hope there will be some retention. At the very least, that deal here would probably be enough to get Keith (at least according to a few other AGMs).

This is my take too - my deal here isn't what I want in a perfect world, but if the Hawks apparently don't want retention, I'd hope at least Koskinen goes the other way. Combined with a Neal buyout and Koski gone, Keith at full cap for two years would be workable. But, ideally, Holland can grind the deal down with retention. Or, Keith is bought out by Chi, and we get him cheap on a 1 year since he apparently wants to come to the NorthWest.

I've read that his contract (or some cap penalty) is nearly buyout-proof, so I don't expect that. It's more likely that he goes to SEA.

Btw.
I don't think Holloway will be in the starting lineup on opening night, I see him more as a mid-season call-up. But I like that Hollway-McLeod-Yamamoto Line tho

I agree Holloway should spend lots of time in Bake this season, but I think he might get at least a few games right out of camp (I don't see Shore or Khaira looking anywhere close to as good as him pre-season). From what I've seen of him, Holloway is just so hungry for the puck, he could really out battle some vets off the hop.

boy oh boy were we all wrong. Holland got robbed. What in the world was he thinking? I don't mind getting Keith. I don't mind losing C. Jones too much. I don't mind adding a pick. BUT giving up all of this and not having CHI retaining anythink of Keiths cap hit. No!