I think they keep both Mikko and Cale if they wise up and cut Toews loose. Problem is they should have done that 5 months ago if they wanted to be smart about it.
I think we sign Toews, Mikko, and Cale to long term contracts and just live with the consequences of a more top heavy lineup. Manson and Girard are the most likely cap causulties to go if the goal is to win another cup with this core.
Once we sign Cale for some ungodly amount of money (thinking $14M), our options for maintaining a competitive team become extremely limited. Either we sign Cale and let Lehky and Colton walk that same offseason, or we let Cale walk and maintain better depth. Neither option looks great, but I think that's the best we can do.
The other option is to trade one or 2 of our impact players before their walk point for a package of less impactful/cheaper players and futures. This is technically still an option for Toews, but I agree that ship has probably sailed and his trade value is diminishing by the day. The bigger problem with trading an impact player for futures is that our team is built to win now. I just can't see the value of reducing our immediate cup chances for the sake of advancing an on-the-fly re-tool with an eye to be more competitive in the long term. It just doesnt make a ton of sense when we've only got a handful of years left before Mack comes back down to earth, and Landy and Nuke start looking more like cap anchors instead of underpaid first-liners.
I would get the logic of trading Toews or Mikko if the rest of the team was still trending up and by trading them we would somehow extend the cup window. But the cup window is pretty well established by now. We've got 4 more runs max before we become a bubble team akin to the current day Penguins. We put ourselves in this position 2 years ago when we signed Cale to 6 years (2 years too few) for the sake of short-term cap savings, and signed Landy to 8 years (2 years too many) for the same reason. We dug in further 1 year ago with 8 year deals for both Nuke and Mack, when we know the ends of those deals won't look as great. We avoided long term contracts on aging players for a long time while we were rebuilding, but we've turned the corner and now have to embrace it. This is the price you have to pay to keep elite talent in their prime at the lowest price possible. We've made our bed and now we have to sleep in it. Might as well push the rest of the chips in, try to win a cup or two over the next 4 years, and live with the consequences later.