But look at how many GM's have destroyed their teams in recent years b/c of terrible contracts. LAK, NYR, MIN, and EDM to name a few. In fairness to Doug Wilson, it's never the huge money superstar contracts that ruin teams for 5 years. It's always the Dion Phaneuf, Milan Lucic, and Matt Moulson type contracts that do the most damage. This happens mostly b/c GM's get impatient and try to build through free agency rather than through the draft. All successful NHL franchises are built primarily through the draft. PIT, WASH, CHI, and BOS drafted almost all of their top guys. So has every team currently on the brink of success like TOR, WPG, and TBL.
I believe this is true for pretty much any sport. Look at the best NFL teams, they generally don't spend a ton in free agency. They may add a couple of pieces to get over the top, but a lot of the core guys tend to be drafted, not signed through free agency. Same with baseball, the Red Sox and Yankees draft well. Look at how much INSANE depth the Yankees have, they had like 500 guys get hurt so far this year and are still winning, because of the depth of their farm system and the quality of their drafting. It's drafts and drafting well that gets you a championship.
The Caps drafted Ovi, Backy, Willy, Vrana, Holtby, Kuzy, Carlson, Orlov. The only significant player not drafted by the Caps for their Cup run was Oshie, at least as far as the top 6 and he was traded for, not signed in free agency. Not that they didn't add pieces through free agency (Niskanen), as every team does that a bit, but if you're primarily building your team through free agency, your team has a serious issue going on and likely won't be using cap space efficiently.