The reason why I bring up Simmonds is because of what I consider our Caps major fault(s) and that is with our young players.
There are two basic kinds of teams: 1) a team that builds through the draft and their developmental system and fills in the holes with free-agent veterans. 2) The other is when your developmental system and draft picks suck and you have to max out your cap to build a team primarily through the free agency. Yeah, there will be a few teams in the middle - but most teams will be one or the other.
But to build the dynasties that we would like the Caps to become a part of, you want to be the first type because of the reality of the Cap-Era. As of yet, we have failed in that regard. Hershey does well year after year, but few guys make the jump for whatever reason. And as for our top drafts; as I pointed out, because of our success during the regular season we will never see the kind of pick that is an automatic NHL player like McDavid or Matthews. Also, the remaining picks all seem to have one major flaw or another: lack of grit, lack of size, lack of speed, no scoring or set-up skill and mostly - no consistency of play. You have guys like Wilson and Vrana who seemingly have made the turn for the better, but still have a step to take .. have taken a while to get to where they're at even now .. and you have to wonder if their success is b/c of their linemates. Then you have the Burakovsky and Orlov's of the Caps. Burakovsky should be cut loose now and Orlov, for all of his upside .. his inconsistency, esp. when we pay him prime defender money, means he has never put more than 1 or 2 games together that showcase what he can really do. And don't get me started on the guys that now infest our 4th line. The only upside was Smith-Pelley's playoff and Cup run. Other than that... comparing our 3rd and 4th lines from just a few years ago to what we have now is depressing to the extreme.
So, if I'm right; that our developmental system and drafting corp suck (overall) then we have to fill from the outside. While our core should be Kuznetsov, Wilson, and a more consistent Vrana - it is still centered on Ovie, Nicky, Oshie and Carlson (I would add Holtby but it seems the one thing we can draft really well are goalies). In a way rightly so, but the thing is Carlson is the only guy under 30 on that list. So our time for being a dynasty is NOW (ie pick up Simmonds or a Top 3 defender) or we need to start thinking about how are we are going to get a few more Kunetzov's or Carlson's on our team ... and guess what, that will cost us Ovie, Nicky and the other guys who's jerseys make up the majority of what you see when you got see the Caps live b/c the rest of the league also knows our first-round pick sucks. Sadly, I don't know what would be the better or less painful way to go about it ... I just hope the Caps management picks one and doesn't keep putting off the decision until its too late and any trade value for our stars are long gone.