We can't win a cup this year or next year, that's delusional and I'd hope that someone operating the team wouldn't get psyched into believing that. Rakell isn't ROR, where we trade for him and all the stars align on our way to the cup. The problem with talking yourself into needing a player is that you start talking yourself into paying whatever price is necessary, rather than doing due diligence and looking for a better deal. There's plenty of wingers out there, we don't need to rush into selling the farm to get RR, just like you don't need to rush into dumping him for spare change. It's a two way street. If there's a massive premium on him, then he can stay in Anaheim and they can continue to draft, and we can continue to draft. Why is it, that people automatically get so defensive - "You don't want our player, then you can suck forever and keep wasting your players careers". It sounds so childish.
Regarding your second point - it doesn't justify it all. That's just being a prisoner of the moment; people that say stuff remind me of why casual investors and gamblers lose all their money. You go in with a plan and when you starting losing, you think the key is to increase bet size to quickly make back the money you lost. So you start investing or gambling erratically and lose even more money. Imagine Holland comes in and thinks to himself - "Well the last GM wasted 4 years of McDavid, so I have to make this work in 1 or 2, instead of my original 4 year plan..." That's shortsighted and he should be fired on the spot. He has never been that type of GM. I get it, random fans want to see fireworks and huge shakeups, but it's just not realistic in business. Winning a cup is hugely unrealistic, the goal is to make the playoffs consistently, cups are not won in 2 years of building, the NHL isn't Sim City. To make the playoffs consistently you can't sell tonnes of 1st rounders, I think that will come back to eventually hurt the Leafs.
