He's 37 years old and costs $10 million. The absolute best chance he has at winning another Cup is if we give him the gift of eating half his salary and trade him to a top contender. And that's only realistic while he's still putting up numbers, so sooner rather than later. That means watching him break the record with another team.
To realistically have a legitimate chance of competing for a Cup with the Caps, a LOT of things would have to go 100% right...
1) Backstrom would have to either come back with most of his ability (unlikely), outright retire (unlikely), or LTIRetire. If we're to win with $10m tied up in Ovechkin, we really need top value out of the rest of our cap. This $9.2m is crucial.
2) $8m is also crucial, so Carlson would either need to get his D game back (unlikely) or be traded for assets that can help us immediately (also unlikely).
3) Kuznetsov needs to find a way to keep his head out of his ass 100% of the time (unlikely).
4) In my opinion, we need an entirely new coaching staff capable of winning a Cup quickly with a team that will need coaching help, and the team will have to buy in completely almost immediately (wildly unlikely).
5) Oshie needs to stay healthy AND maintain his compete level and production (unlikely), or be traded (feels unlikely, but maybe).
6) Mantha probably has to go. And if he and/or Oshie go, their cap hits need to be invested in impact players that contribute immediately (doable).
7) We either need another high-quality, top-6 center or Strome, McMichael, and/or Lapierre need to break out big (possible if we get Nick's cap hit back, but any of those 3 becoming top-flight Cs in short order seems farfetched).
8) We need to shore up the defense affordably (possible if another bunch of things go 100% right).
It's not impossible, but with Nick holding us hostage and the organization showing almost no signs of doing ANY of these things, it really FEELS impossible.
CCR is right that we have another chance this summer to dramatically reshape the roster, but we just had that same chance and hedged, so I wouldn't hold your breath. And let's be real, a transformation that profound in one offseason is very rare. I can't really think of one, at least not any that included so much cap tied up in declining players unlikely to leave town...