Quoting: dtd_tank
The Penguins were gifted a top 2 pick for 4 straight years. Let's not act like that's normal.
Looking back at past winners, I think WSH is the prime example. They had a rough spell and got Ovi & Backstrom out of it. Otherwise, they've drafted & developed well. They have done it "right".
LAK also did it right: hit on draft picks, and won with heart.
BOS also did it "right" I think, but for as successful they've been by making the playoffs, they only have 1 Cup to show for it.
STL's win doesn't happen without ROR, who was acquired by trading the guys they may have been able to re-tool with (but likely wouldn't have put them over the edge like ROR did).
CHI had a good team but I would put them in the PIT bucket of lotto "luck" that worked out for them.
So, doing it "right" doesn't guarantee anything. There's not a right way to do it, IMO, it all depends on the team.