This is all true. And I think it's great for discussion you pointed it out. But... the devil is in the details. While those champions you listed won by leveraging high picks, so did Tampa (a #1 overall pick in Lecavalier) and San Jose (trading a #3 overall Brad Stuart in a package for Joe Thornton, a former #1 overall himself). Calgary is an interesting case for sure, they traded a Hall of Fame player in Joe Nieuwendyk for young holdout Jarome Iginla (#11 overall from Dallas).
And of course, the same holds true for our 90s Red Wings, who became the dynasty with The Captain #4 overall pick Yzerman.
So here's a handful of things I take from this:
1) The Red Wings need another blue chip, Zadina-level prospect or two in the next few years.
2) I don't blame Ken Holland for not having that elite talent with his draft picks.
3) I do blame Ken Holland for not putting more emphasis on acquiring top picks years ago. Keeping the roster floating in purgatory with veteran stopgaps has only slowed our fall.
4) And I also think it's pure incompetence an organization and Holland could fail to improve a completely awful blueline via draft, trade, or free agency since 2012. We're not talking Lidstrom 2.0, we're talking about having a top 15 blueline rather than bottom 5.
Honestly, it feels like too much pride. A level of hubris that they could beat the odds.
I can't say I disagree with anything you are saying, that is a very well written post that is written based on logic. My point was never anti rebuild or even to defend Holland, my point was simply against those that believe tanking for a decade is the only way you will have any success. This group often cite Chicago, LA, and Pittsburgh as to proof as to why they are right.
You need top talent to become an elite team, and trading away valuable assets helps you acquire that talent (like the Iginla example). This is why its so important to trade for picks, because lower end picks become a crap shoot. Its like a raffle, the more raffle tickets you have, the higher the probability of hitting a winner. I am for all of this, however, I am not for trading/buying out every player we have over the age of 25 with the intention of being dreadful for the next 5-7 years, I don't want to become the next Edmonton, Buffalo, or Arizona. Not that you are implying this, just putting my point out there.
To touch on all your points:
1) Agree, and I think this year we will likely land another top 5 pick. Hopefully we draft a can't miss #1C or elite D-man.
2) Agreed, its very hard to land elite talent now a days when you are at best picking in the mid teens or later.
3) Also agree. The team prioritized the streak, there is no doubt of that. Was it Holland, Illitch, JD, all of the above? Who knows.
4) I'm not sure why the blue-line has been their Achilles heel, but it has. Outside of Kronwall, they haven't drafted a legit top pairing guy in almost 2 decades. That is bad, there is no defending it. Maybe the reason is that they have done a bad job developing? Maybe it's that they fail to successfully evaluate a D-mans ceiling, and focus too much on where they are at the time of the draft? I'm not sure. I really thought Smith was going to become an elite D-man and that Sproul would become a top 4 guy, but we all know what happened there