I doubt Chicago takes that but if the isles r in playoff position than this makes sense for them. I feel like Chicago would ask for something extra to take Bailey though. I’m not saying they deserve that but they would ask.

Aho and Holmstrom aren't worth much, if anything. If this is a deadline move that means the NYI's are in the playoffs, which would put that pick in a mid-late draft position. I won't say that Bailey is 100% a cap dump at the deadline, but right now it is looking that way. Regardless, Bailey isn't worth anything to CHI, specifically, because of their status as a rebuilding team. And you want almost 50% retention. Which if you are taking up one of CHI's retention slots, you might as well just utilize the whole 50%, because I think the retention slot itself is probably worth more than the actual amount retained, at this point. CHI will want a top prospect and a 1st. This isn't that. CHI declines.

Always better to separate your cap dumps from your impact acquisitions - including Bailey here drags down the overall compensation on this package since he's not a player that Chicago would have any interest in. As said above, it would also be worth getting the full retention here, since you're conceivably paying Chicago for the retention slot and that extra cash doesn't really matter to a big market team like them (plus that extra $1.6M in cap space is worth its weight in gold at the deadline - you can add another impact player if you need with it).

Even if you move Bailey separately, the package isn't enough. Aho is the type of guy every team has a handful of as a 7th D - he's already 26 so I don't see much, if any, upside going forward. Holmstrom is a decent prospect, but not a top one (12-31-43 in 68 AHL GP this season is good, but not top tier) and the 1st is most likely in the later third of the first round. Gotta add a little more juice to it to get Chicago to bite, probably a player like Dufour over Holmstrom, or an additional high pick if you don't want to upgrade the prospect. But it's gonna be an upgrade *somewhere*.

I agree, I saw this ACGM and the underpayment was my first thought. As a CHI fan, is there a specific isles prospect you have in mind?

Would something like this work?:
-bailey
-1st
-buldoc/wilde

Unfortunately, the isles only top prospects are Raty and Dufour and they can't give one of them up for 1 year of Kane. Would a roster player like Beauviller be good instead? Then CHI doesn't retain?

Bolduc and Wilde move the needle even less than Aho and Holmstrom. Plus, we really don't need any more D prospects, but being right handed might help. Honestly, if the NYI's can't give up a Whalstrom, Raty, or Dufour, or a better selection of picks, they shouldn't be targeting Patrick Kane.

Understood, appreciate the insight. Wasn't sure if no salary retention would keep the top prospects out of the equation.

I feel ya. No one wants to give up their promising prospects and high picks. But super stars like Kane will always come at a price, even if he is a UFA after the 22-23 season. Also, the 50% retention is more so to help other teams who are closer to the cap. CHI has the cap flexibility that the retention doesn't matter to them either way. If they could retain his entire cap hit they probably would as long as some good pieces were coming back.