Considering today's scouting system, stat availability, video resources and general transparency I would say Iginla, Bouwmeester and Phaneuf.
All were (more or less) all stars at the time and netted late firsts plus b/c-level prospects, or even worse, a bunch of 3rd liners. Regher trade was horrendous too, but they had to pay to get rid of Kotalik I guess.
Darryl's six month psychosis and Feaster's time really set the franchise back several years.
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