I knew as soon as I posted Jamie Benn would be the first guy mentioned in response
I completely agree that you can hit a home run and get great players later on in the draft. Benn's amazing for sure, but I personally wouldn't put him in the same category as guys like Crosby, Tavares, Ovi though. He won the scoring title last year and still didn't even finish top 10 in Hart voting. The type of guys that year after year are in the Hart trophy mix
usually only grow on one tree, and it's called the lottery tree. And it's about odds as well. The odds of the Leafs developing a 5th rounder into Benn are next to nothing, but the odds of them getting a one day Hart trophy candidate out of Auston Matthews are really good.
I realize there's many ways to build a cup contender. The Montreal example you gave is a good one. LA didn't follow the suck for years blueprint either (although that 2nd overall Doughty pick sure helped). In the end it's really just my personal preference for them to build a cup contender by following that plan and getting those top 2 picks and then building around them for the better part of a decade. I have no interest in being a good team for a few years and then back to reality. I want sustained success with a core of superstars(again, just my personal preference). I look at what Chicago and Pittsburgh did and that's the type of team I want. Once you have that Toews/Kane or Crosby/Malkin combo it's hard not to be a contender it seems. You obviously need other pieces (Keith, etc.) and it hasn't resulted in multiple cups for PIT due to many different reasons, but almost every year going into the playoffs for a good 7 year span people considered them one of the cup favorites. I figure the Leafs are already as low as they can be so there's no better time to do this than now...what's a couple extra years?