A quick read, and I only found one response for the Dallas Stars, which was to hire Jim Nill. Pretty snarky, because he is a good GM who hasn't got us to the Cup. Not sure the age of that poster, but my memory goes further back!
Another more recent flub was to draft Gurianov in 2015 over some other very talented players who have done better. But, we got our 1C in round 2, so some redemption. Also, Nill did tend to go "off the board" several times on the first round pick. Lately, he seems to be betting better, with Wyatt Johnston in the first round, who looks great and getting Stankhoven (who most fans wanted to be picked first) in the second. It might be a much better sequel to the 2015 draft.
Going back further, it was trading several no. 1 picks post-2000 to "keep the core together" which never worked out, obviously.
Another post-2000 blunder was believing they could do no wrong in the UFA market. They let Hull go (probably the right move) and brought in Audette and Turgeon thinking they would just plug right in. They didn't ever develop any chemistry with anyone then on the Stars roster.