There's more than one way to skin a cat, but when you look at teams that are perennial contenders, virtually all of them got their franchise forward(s) in the draft lottery. You have the odd example like Point & Kucherov that were taken later, but those are the exceptions & not the rule. That's why when a player like Jack Eichel is available once every decade or so, you give up whatever the asking price is and you live with it.
When it came time to evaluate players at the pro level, The Charlatan & his crew were among the best in the league. They rarely lost trades. They didn't make too many bad UFA signings either.
The problem with The Charlatan is, he always talked about never giving up the future to win now, and yet I can't recall ever seeing someone so blatantly give less of a fuck about the future. His biggest two mistakes were right at the beginning: Keeping Trevor Timmins and hiring his buddy Sylvain Lefebvre to coach our AHL team (and then keeping him there for six fucking years).
Had this team been just an average drafting & developing franchise, we wouldn't be in such shitty shape and he'd probably still be employed.