this actually does look plausible depending on CHI's interest in retaining for picks.
it has a quality prospect coming back and 2 1sts while close to the 18% retention range, so should check all SJ's boxes

I would imagine Chicago would want a quality prospect to retain for 4-years.

Really unlikely to get double retention on a guy with that much term.

I think the hawks would be open to it but they’d need a first round pick minimum. They also might not even be able to considering their retention slots will probably be taken up by Kane, toews, and probably McCabe

Yeah, there's also Domi as an option, and I do think in the future they may need to retain on Seth Jones. So, they could be in a situation where they could be down to 1 slot per year for 2-4 years.

Yeah, I think it’s way more realistic for them to take on cap dumps than double retain for another team

That's why I think it would have to be a prospect/young player that they are super high on since they won't know that 1st round pick could be. Over that time, they probably could get a 1st+ in value by taking on dead cap/flipping guys.

As accurately stated by several of you above, the chances the Hawks even have a retention slot to use this season are pretty slim. Kane, Toews, Domi, AA, maybe McCabe, maybe Murphy. They won't diminish their ability to maximize their return on their own assets this trade deadline to help the Oilers for less than a 2023 1st plus. 4 years and $8m is a big ask!

That is not enough for CHI to retain $2M/year for 4 years.

Wings give up Bertuzzi for a meh prospect and a pick 3 years away. No

Chicago retains 2M on Karlsson for 4.5 years for a 2nd, 3rd and 4th round pick, Going to cost a hell of a lot more than that to retain for over 4.5 years or so.

Detroit passes, A meh prospect and a 2nd round pick 3 drafts later. Doesn't get Bertuzzi at full value let alone 50% retained.