It's looking at the team's cap situation and saying "don't worry about it, they'll be fine" while a team that just finished in 30th sits within $50,000 of the salary cap with millions in rookie performance bonuses likely to spill into 2017/18. It's saying Loophole Lou can do anything while the Jared Cowen buyout, which Lamoriello publicly announced four months before the paperwork was filed, sits in court while an arbitrator decides whether it's even logistically possible two months after the fact. It's repeating the echo that this team has an expertise for cherry picking the undervalued, and being the first to lose the game of chicken and give up assets for a goaltender in the summer.
None of these things individually mean that Leafs management are doing a bad job. In fact, even if you combine them all and stack them against what else has happened in the last couple of years, that group is still doing an overwhelming amount of good. But being mostly good doesn't mean that we should brush the curious off as "they know better than us". That creates a yes-man scenario where people start to buy into themselves too much and start making mistakes because nobody's there to second-guess them.