It's all about potential and having hunger as a GM. Holland is too complacent because of all he's already won.
And you're forgetting they got within a game of making the Finals a few years back. Struggles since then, but I think he'll turn it around.
Oh and Yzerman traded Quincey for a 1st round pick
Which was largely done on a roster he inherited & a hot goalie that he got really lucky on. They missed the playoffs last year by 8 points & he's on the outside looking in again so far this season. So looks like he's gonna be 1 for 3 in playoff appearances? Sorry, I for one don't buy into the whole "Stevie is the front office messiah" thing at all. Anyway there are two internal candidates, Jim Nill & Ryan Martin, that should be ahead of him in that line for Kenny's job if he decides to hang it up in the next couple to few years.