Pretty common denominator in those SC winners. They drafted their #1 C. We've run at a deficit for draft picks during our rebuild. Last 5 years, the league gives you 35 by default, we had 34.
We could have done a better job of asset management. Ive said this in another thread.. But dont make the trades for Liles/Bolland, and do trade Grabo/MacArthur for picks at the 2012/2013 trade deadlines when a lot of people wanted those guys traded, and the net difference would probably be an extra 6-7 picks, including 4-5 2nd rounders. Thats pretty substantial.
Dont trade for Liles/Bolland, do trade the two guys who CLEARLY were not part of this team longterm (which was said by a lot of people, and is now shown to have been an accurate prediction), and we'd have a boatload of extra picks, and ultimately the team would more or less be in the same spot it is now. Yes, Bolland has played well for us, but at the end of the day, Bozak is already signed longterm, and is the calibre of player you'd expect as a 3rd line C on a contender. If we just wanted a shortterm fix, we could have found it in free agency. If we wanted a longterm fix for 3rd line C when we traded for Bolland, then we shouldnt have resigned Bozak because thats what he ultimately is.
This team doesnt build to be a sustainable SC contender, they fill shortterm holes by trading picks, holes that ultimately will need upgrades via some other means, indicating that trading those picks away really isnt helping us build towards being an actual contender.
If you already have a contending core in place, it can make sense to trade picks for secondary veterans to "go for it". But we're not at that level yet. Draft picks are lottery tickets, not guarantees. But as a philosophy, if you can acquire an extra 5-10 picks over a five year span as opposed to losing a few extras, thats how you increase your odds of finding Bergeron, Stastny, Backes, Datsyuk, Weber, Letang, Keith, etc in the draft.