How could I forget Sean Avery......as much as I have tried!
Yes, Glennie was brutal. All the draft gurus thought he mostly got points because of his linemates. I recall them interviewing Niewy about the pick and he mentioned that they needed a RW. Drafting for position rarely make sense, and Glennie was a reach. He was similar in some ways to Richard Jackman, picked in the first round in 1996. I saw him in a preseason game and thought he looked NHL ready, but then the drinking problems started, although I think in both cases, they were there and the Stars didn't do their character research well enough.
So, in no particular order other than in order, we have Jackman, Glennie, and Guri in the drafts. And Avery, Turgeon, and Audette in the UFA categories of mistakes. After that, there are all the garden variety draft picks that didn't work out, like Honka and Tufte, who, while we saw the reason to draft them, didn't work out at all.