It has always struck me that Eeyore always looks at other players solely from his own perspective; that of a grinder-type player. He had some talent but made his career by working his tail off. If he sees a guy that does not measure up to the standards he had for himself, he views that as that player being a slack-ass. His biggest failure as a color guy IMO is that he never has been able to realize that not everyone works that hard and some guys don't have to. Lemieux, while an extreme example, illustrates that point perfectly.
Yes, in an ideal world, every player would give 100% of themselves to improving their game and playing the best they could. In the real world, that doesn't happen. Some guys make it by hard work and will, others by skill, and the rare ones do both.
Jaromir Jagr was another Eeyore target. Eeyore would always complain about about his lack of attention in the defensive zone, even on a night where Jagr dominated offensively. To me, that is like complaining about lack of trunk space in a Ferrari.