In terms of disappointments I would argue the 91/92 season has to be considered. Just a couple years removed from the championship, and didn't even make the playoffs. And smack in the middle was the infamous Gilmour deal.
The only good thing was Roberts getting 53 goals.
But the team boasted Roberts, Macinnis, Fleury, Makarov, Nieuwendyk, Suter, Reichel, Otto, etc and still managed to miss the playoffs.
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