Nazem Kadri wasn't a #1 overall pick, nor was PK Subban. And the latter's bridge deal turned out to be a pretty epic mistake.
I'm just going to post this again.
That is a chart of every 2nd contract handed out to a top 5 pick since the 2nd Bettman Lockout.
Now, look at all of the ones that are 5 years or longer. Ask yourself, "which of those turned out to be a bad deal"? My answer is "none of them". Granted, a couple of the recent ones are probably too early to tell.
Ask yourself, "which of those contracts would the team have liked to extend for an extra year or two at the same cap hit?" My answer is "all of them", with the possible exception of Ovy and Backstrom only because those two are long enough as it is.
These deals tend to work out okay.