I've said it like 2 times this year. The Leafs will not win the cup under Babcocks current contract.
Maybe if he signs another extension and by then they've tanked like 4 more times.
The parity is way too high in his league for a 1st rounder to matter as much as folks think.
When Connor McDavid was in the lineup after he return from his injury - the Oilers won like 12 out of the 32 games they had left. What an amazing finish.... And when he was injured the Oilers won 11 out of 26 games... Austin Mathews isn't going make much of a difference. They need a lot more pieces.
That bolded statement is absolutely, positively, 100% false. Pretty well the ONLY way to build a perennial Cup contender nowadays is to drop to the bottom and draft like mad.
Star players don't get to free agency except in rare circumstances and to trade for one forces you to deplete your depth. The one way to build up a bunch of high end talent is to draft them.
The thing about what the Leafs have done is that it's not just one 1st rounder. They've finally decided to take their time, develop these kids and do it properly.
They have three top-5 picks in the fold now in Matthews, Marner and Rielly. They have another top-10 in Nylander. They have Pittsburgh's 1st this year, so there's another one, if they keep it. Won't get a great player in the high 20's, but should get a good one. They also have the 31st overall pick and another one in the 2nd round (Washington).
They should get another decent 1st rounder in 2017 (don't think it will be top-5, but you never know), plus they already have three 2nd round picks in 2017.
Will those players be as good as their draft position indicates? Who knows, but you don't get them unless you're in those early spots in the draft.
The way it is shaping up, I think the Leafs will be a really, really good team in 3-4 years. They'll start climbing the ladder pretty soon, I hope.
By the way, your entire post is completely contradictory. You say the 1st overall doesn't matter, then list off how good the Oilers were with McDavid, and how lousy they were without him. Doesn't that prove the point? That said, the Oilers are a completely different animal, they have screwed that up in every way imaginable. They let the inmates run the asylum and the results showed, which is not unlike what the Leafs had been doing for 45+ years until the Shanahan regime took over.