Yes indeed. Even if they win they ought to attack the off-season as though they want to at least maximize their chances for further success in Ovechkin's remaining three seasons under contract. Win it all and it should remove any doubt that 8/19 will be lifers. You'd think either way that Leonsis will pay up for Trotz (he paid up for Scott Brooks with a lot less justification) and do what it takes to lock up Carlson & Wilson. There will be losses. It could be Grubauer, Orpik & Burakovsky along with UFAs Beagle and perhaps Kempny. Those two UFAs will be the toughest to hash out on a team-friendly basis IMO. Winning it would not only give the know-how for the rest of Ovechkin's career but also for younger guys Orlov, Kuznetsov, Wilson, Vrana and Stephenson as mature credible leaders. Overall, like I mentioned in the draft thread, it should give confidence, clarity and decisiveness to the front office overall in terms of their organizational identity and what it takes. It would be massive. Even the younger guys that aren't playing just following along and seeing all it takes can take a lot of lessons away and be motivated in the off-season to strive to be the next man up. There could be some risk in backing off, relaxing organizationally and just turning things over to youth that maybe won't entirely have the goods when it comes to Djoos, Bowey and perhaps Boyd as an NHL center. But they can also rightly stop sweating the regular season so long as the internals are on track and be more open to take some chances on youth, esp. in depth roles, with eventual trades as Plan Bs if it doesn't work out.
The coaching market is interesting. Everyone that fired someone has already made their hires (CGY with Peters, CAR with Brind'Amour, DAL with Montgomery & NYR with Quinn). The Islanders with Lou probably will end up making a change IMO but does anyone else enter the market? Does Boudreau stay in Minnesota under Fenton? Vigneault is out there for someone, perhaps the Islanders, but the lack of widespread openings should further help the Caps in not just retaining Trotz but the rest of the staff for now.