1. Alexandre Picard (1st round, #8 overall, 2004).
Why were the Blue Jackets so terrible for almost their entire first decade in the league? They had arguably the worst GM in the league to start, and kept him around entirely too long. If you want proof of that: this pick is a great place to start.
Top-10 picks are rarely traded at the NHL Draft. Top-5 pick trades are even more rare. If they are traded, they are usually very expensive to acquire. This whole fiasco should serve as an example why that's the case.
The Jackets owned the fourth overall pick at the 2004 draft, but they traded out of it; acquiring picks #8 and #59 overall in exchange for it. From a value perspective, it was literally pennies on the dollar. Blame it on lack of data at the time if you want - but in this case, it did not work out well for Doug MacLean.
The Carolina Hurricanes landed pick #4 and happily select the player they coveted: Andrew Ladd. While he did not become the high-end scoring winger many presumed he could be, he did become a very serviceable middle of the lineup guy who played in 1001 NHL games, scoring 256 goals and 550 points.
In exchange, Doug boasted to the press that he was still able to secure the player he was hoping to get with that 8th overall pick: QMJHL winger Alexandre Picard. I didn't see what they liked about him then, and I still don't see it now.
Picard was big, and he was physical. That was about it. He wasn't a very good skater, and there wasn't any obvious trait about his game that stood out as translatable to the NHL. He was a prolific scorer at the junior level by being bigger and stronger than the competition. That could have carried over to the NHL, I suppose. But, at 6'2" and around 200 pounds, he wasn't big enough to compete in that regard.
This looks even more odd in hindsight when you consider that they chose Picard - a big, scoring left wing - just two years after picking Rick Nash. This selection never made sense, from any perspective. Picard wasn't a top-10 worthy player, even in a weak draft.
Trading this pick actually would have made some sense, had MacLean actually gotten fair value for it. Perhaps an NHL player to help his team immediately. Or, maybe he would have been better off acquiring more depth picks than what he actually got. Instead, to move back 4 picks in a draft that was already pretty weak with a top-5 pick; all he got was a late second rounder (Kyle Wharton) who would never play in the NHL.
In the end, the only thing worse than MacLean's asset management, might have been his drafting. The two players taken after Wharton: Brandon Dubinsky and Alex Goligoski. Ouch.
The one saving grace for selecting Picard is the fact that this was a weak draft. The best players taken after him in the first round were low-tier second line guys at their peak, but at least they had NHL careers. That's more than we can say for Alexandre, who amounted to 67 games and 2 assists across parts of 4 NHL seasons.
Once the team's drafting and development got better, they actually had some competitive years. But, in the early going, it was rough. They either picked the wrong players entirely, or did a dreadful job developing them. We can only look back and wonder how good things might have been for this franchise with an actual plan in place in its early years.