As stated previously, it doesn’t work the vast majority of the time.
It doesn’t work the vast majority of the time because only one team wins each year in a 30 team league. Now it’s a 31 team league and soon it will be 32. It’s as competitive as ever and it certainly is hard to rebuild.
A lot needs to go right.
You need to make the right picks, not just with your easy, early 1sts but in the later rounds too, to cultivate some depth.
You need guys to develop right so you need some luck and a good farm team.
You need guys to play the right positions to fill out your roster. That’s usually not going to work out perfectly on its own, so you have to make trades and free agent signings.
Which means you need to be a destination players are willing to sign in or waive their NTCs for, in some cases. And then you still need to sign the right guys and make the right trades. Gave up on a prospect too early and he blossomed after the trade? Ouch. Signed that big name but he started to decline after a year, at 28 years old? Ouch.
And you need the right coach. And the right mix of players. Super talented but you don’t have a strong 4th line that can PK and forecheck? Great fleet of puck movers but you give up too many prime chances in the slot? Not the right mix of players. Gotta keep tinkering.
So, no, it doesn’t usually work. The Capitals haven’t won it all. But they’ve been a favorite or a team that’s been considered a genuine competitor annually and they’ve had the excitement of Ovechkin, Backstrom, etc. Those high picks didn’t “work” for them in terms of winning the ultimate prize, but again, only one team can each year and those teams usually have everything going right. That’s actually why three teams account for like 8 of the last 12 Cups. Because they had the right mix in almost all of those critical areas. All those other teams that got it 85% right fell short. Or maybe won one in there. The Lightning have Stamkos and Hedman but they haven’t won it yet.
But I’d rather be in the shoes of Lightning or Caps fan where we have the fun and excitement of watching elite players put up elite numbers and we’re always in the playoff/cup hunt than be in our shoes where we have watched years of teams that range from blatantly mediocre to pretty damn good get backstopped to success by a legendary goalie. Our seasons are so frustrating. We’ve been a good team but we haven’t always been a fun team. So, personally, even if our rebuild falls short and we end up no better than we were for the last decade, I feel it will be worth it. As we were this past decade, or as the Caps and Lightning have been (just as examples) we will be a playoff team and a team that competes, but hopefully we will cultivate some talent and become a lot more fun and a lot less frustrating to watch. Ultimately, the goal is obviously to win, but if we don’t how is it any different than now? This season would be a lot more fun if we had a guy on pace for 80+ points or 50 goals, even if we were still a lottery team.