The first half wasn't good at drafting either. He was lucky to get here at a time when a lot of future All Stars were already on the team, and then lucked into Zubov and Weight in later rounds. In all his drafts from 1989 to 1999, he got one good player (Kovalev) in the first round. All other first rounders were total busts or 3/4 line role players. Since it takes time for draftees to mature, his misses weren't obvious until the second half of the 90s when he stripped the team of all the young talent in awful trades. Weight, Amonte, Zubov, Nedved, Kovalev, York, Savard all were sent away for lesser, older players (except Savard who was traded for Lundmark, who was technically younger, but was a bust).
His trades early on were better. The trades of Messier and Gartner (getting him, not trading him away) worked out well. The signing of Graves worked out. Nicholls for Sandstrom and Granato was a loss though. Pretty much every trade after the Cup was a loss. Also, Neil Smith forgot - FORGOT! - to put Ray Sheppard on the restricted FA list and he became unrestricted. The guy was already a young second liner who was obviously going to be a first liner, and he went on to score almost 100 points for Detroit.
His biggest move (Messier) worked out and that's all anyone remembers anymore, but his overall tenure was awful. I suspect if he did nothing and just kept all our budding stars, we would've won more than one Cup. There was just too much talent there. By 1992, the team had 10 guys whowould go on to play in multiple All Star Games in the future. It's pretty amazing that this team had only one Spring when it was viewed as a serious contender. Again, it worked out that one spring, but we had such a plethora of talent and then our window was one season?