I’d much prefer they approach this season as lost and look to do everything the can to prepare themselves for 2-3 years from now. I don’t think Karlsson fits this timeline. He’s much more of a win-now type acquisition.
I doubt we'll see such an arc but I'm also not sure if we can rely on their structural integrity being any better 2-3 years down the line. Such an arc is too complicated and not without risk or assurance of it paying off in time. This may be the last season where it would be feasible to load up on picks that maybe could be fast-tracked just enough to be in the league while 8 is still around. But I doubt that's overly appealing in the here and now compared to more aggressively trying to make the playoffs. They generally do not do delayed gratification. More likely it just...stays flat. Stays just about where it has been post-Cup. It's just about trying to compete every year minus much in the way of prime younger, developing assets.
We'll see how it goes. If there's a further in-season wobble that puts the playoffs in even greater danger that's when I'd expect a trade or perhaps a coaching change to help stabilize things. Hard to believe they'd pull the pin on the season unless injuries make that decision for them. Otherwise IMO they're just sort of resigned to being a bubble team essentially for the rest of the Ovechkin Era. And then they'll suck forrealforreal.
One thing that does stick out currently is that only Kuemper is signed beyond Ovechkin's deal. Orlov & Jensen should both get more than three years if re-upped (same with Wilson) but it does highlight the structural flexibility they may want to maintain. You wonder just how selective they should be then next summer when they may have a lot of cap space. Would they resist the temptation, at least as it concerns term, in order to maintain flexibility post-Ovechkin? Depends on the player you'd think but it could also give them another pivot point.
For the Caps I don't think it's age so much as poor sense and athleticism that hinders them. Boston has a fair share of older players but they think the game at such a high level that it's a benefit. Whereas mentally the Caps haven't earned nearly the same advantage.