I am not to sure that answer is as black and white as that. In my opinion, I genuinely think the Stanley Cup is the hardest trophy to win in pro sport. Of course there needs to me notable signs of progression in the meantime that mark success, but at the end of the day, this roster would be Cup or bust regardless. Lets pretend our stumbling block was the 3rd round vs. 1st round. Wherein, say we just couldn't get past the conference finals the last 3 seasons as opposed to the 1st round. IMO, The goalposts would just move. The criticism of this core, the coaching staff, and Kyle would be the exact same. "This team is not built to win it all". Sure there may be more folks out there that would be on board with the vision, but I really don't think it would be as many as some would think. Afterall, Kyle has been a controversial figure in Leafs Nation from almost the beginning of his tenure.
For me, knowing how difficult it is to win it all, the only approach is to maintain a future focused approach at all times. Of course there are times when you need to put a heavier stake of chips into the middle of the table, but I do not believe in the "all-in" approach. Not in the NHL at least. There is way too much parity in the NHL and all 16 teams that make the playoffs have the ability to win a 7 game series against any of the other teams in any given year. If a team with Sakic, Forsberg, Tanguay, Foote, Hejduk, Blake, Kariya, Selanne...etc can get bounced in the 2nd round pre salary cap, imagine how hard it is for teams to win it all by pushing all their chips to the middle in today's NHL.
I will begin to lose faith in Kyle when he begins to compromise that future focused approach. His back has been up against the wall for a long time now, and he hasn't shown that desperation that we'd normally see from GM's in his situation. If it were up to some posters in this forum, Nylander would not have been a Leaf at this current time, Marner would have also likely been dealt by now and we'd almost certainly not have the prospect pool that we do. All to have the same ultimate outcome in the playoffs, with maybe 1 or 2 series wins under our belt. Whoopty doo.
Like I said, I think sustained success year over year is our only way to achieve the ultimate prize over time. I will take as many first round exits as it takes to win the cup eventually.
For the record, I am not one of those Dubas supporters who blindly support every move he makes, nor am I one to suggest he's not made any mistakes in his tenure. He's made plenty. But when assessing his entire body of work, this is a very intelligent man, and a bright hockey mind. I genuinely feel like we'd be foolish to part ways at this point.
Lastly, I am definitely guilty of being the guy who props Dubas up by referencing the failures of other GM's, and specifically Lou. The reason I do that is to bring forward the widely available alternative. More importantly bring forward the philosophical adversary to someone like Kyle. Not to suggest anyone who wants Kyle gone, wants the exact opposite version of him as a replacement, but to some degree there is some truth to that. A lot of the adjectives that have been used in a negative association to Kyle have been inexperienced, pushover, spineless, over analytical...etc. Lou just so happens to represent the exact opposite of that narrative. But you could insert any of the following GM's into that category and get the same outcome: Rutherford, Burke, Hextall, Holland, Fletcher...etc.