I'll be honest, I am pretty unhappy. For a while it was easy to dismiss these "small bad moves" but it's getting harder for me. I'm not going to give the Leafs management credit for winning a draft lottery; that could easily have gone the other way.
What exactly have they done in the last 18 months or so to instill confidence in fans? The last time I was impressed with this management group was when they traded Phaneuf. That was unquestionably a strong move. After that they signed Rielly and Kadri to good contracts. That's fine, but how much credit should I really give them for that? Rielly was easy, and Kadri was signed to a great deal, but he was coming off a down year. I would have been really mad if they did something stupid like sell low on him, but if I'm being honest, I'm not going to sing their praises just because they didn't do something dumb.
Other than that it's all been a bunch of crap. Re-signing Polak, signing Matt Martin, two very sketchy drafts outside of the first round, a dubious contract for Hyman, signing Marleau to a ridiculously overpriced 35+ contract with a full NMC, and signing Hainsey as a "top 4 man". None of these moves are going to kill them but it's adding up, and if they're doing dumb things now, why should I assume they won't do more dumb things in the future when the stakes are higher?
I'm not calling for anyone's job (yet), but it's past the stage where I'm willing to give Lou and his guys the benefit of the doubt.
(this post ended up being more of a rant than I intended, sorry)
edit: I'll add this. If they lock up Nylander this summer long term, that will help earn back some of their credibility in my mind.