It's got to be Button for me. The Savard trade was a head scratcher the minute it was made, and was worse when Gilbert was fired almost immediately afterwards. It made no sense given the coach/player relationship was the reason Savard was traded. (Savard was traded Nov 15 and Gilbert fired Dec 3).
You then compound that with trading Giguere so that they could protect Fred Brathwaite in an expansion draft, and buying out Martin St Louis' contract. I was young and wasn't really able to provide my own opinion on a player's skill and potential at the time, but I know my Dad was livid when they let St Louis go.
Signing Turek to a large contract after a 20 game stint was also shortsighted but not the worst. Turek ended up restructuring his contract a few years later to help the team out.
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