I don't even know why the argument's become about how often the first overall picks win the Cup.
It's utterly irrelevant. Completely and utterly irrelevant. The first overall pick is one player on a roster of 22 with no guarantee of how good he may be, with no hand in the building of that franchise. He's one of many, many pieces. He may be the best piece of 'em all, but as it was shown throughout history and most recently with McDavid last Spring, he could be the best player on the planet, and he can even drag that sorry excuse of a franchise to the conference finals, but there's only so much one player can do, regardless of how good he is. By the way, fun exercise: Find me those great players like Lemieux, Gretzky, Orr, Howe, etc. who won Cups when they were surrounded by bad players.
(Hint, it's not a coincidence Lemieux never came close to winning anything without Jagr, Coffey, Ron Francis, Mark Recchi, Stevens, Murphy, Trottier, but I digress. How many Cups did Gretzky win without Messier, Kurri, Anderson, etc.?)
Getting the first overall pick never has been, and never will be, a guarantee for a Stanley Cup. It is, however, the most consistent and probable method of getting high end talent in your franchise. And the kicker? You don't even need to convince someone to come play here or negotiate with another franchise to send a player (that they would never trade in the first place) here.
We've seen throughout history that free agents don't want to come here (Not that I mind, personally), but we have seen that once players get here and spend considerable amount of time here, they don't actually want to leave. They want to stay here. What better way to get them here than drafting 'em?
And worrying about what they're going to make after the ELC, so much so that you're not sure you'd want a player like Bedard? Come on... Nobody in Toronto or Deadmonton is bitching about the Matthews/McDavid contract, except that Matthew's contract probably didn't have enough term. The money, though? Nobody cares.