He's quite obviously stuck in the past in terms of how a team should be built, loves to trash his own players to try and excuse the fact that he doesn't know how to develop prospects, is wasting Carey Price, told the media he wanted to emulate the "Chicago culture" in MTL...

I think also he tends to make "bold moves" to try and shake things up and make a big impact but they almost never work out, so he ends up looking like both a cutthroat, emotionless GM and an incompetent. Poor habs fans.