What kind of cap hit do you have in mind? I mean, Caufield (or 9OA, or an asset of similar value) for Sergachev would still be less expensive then a 5M OS compensation.

Giving up a pure goal scorer that broke every record on his way to the NHL and his 3 ELC years for a top pairing defenseman that's about to get paid for me has no incentives especially with the amount of prospects at LD that we've got. Most likely they won't be as good as Serg (Maybe Struble) but for me trading an ELC for Serg isn't good assets management on the long term knowing fully that the league will have a flat cap for two years.
Nothing against Serg, I'd love to have him back here but it's only bad timing. It's like if we were trading for a middle six center now ... Might've been usefull couple years ago but we good now.