Well, there's the Dallas trade for Dave Gagner (they're lucky Hogue never hit his full potential or this would be worse), dealing for an over-the-hill Kirk Muller, and of course, reaquiring Clark and getting a disgruntled Schneider for Kenny Johnsson and their 1st that year (Roberto Luongo). Ironically, their terrible drafting prevented this from being even worse, as most of their players busted; if they hadn't...
Yeah the Clark trade was dumb (and does fit your narrative) but all this together is more than counterbalanced by trading Clark for Sundin in the 1st place.
Gilmour had a couple of superstar level years here and carried the team. When he started to decline and was no longer able to carry the team the way he did, that was the end of it. It was a veteran team that was bound to regress no matter what, that's the way I remember it anyway.
Agree there were some bad trades and of course bad drafting, something I think a lot of people don't understand who think Dubas is the worst GM in the league. Say what you want about him and he's f***ed up a time or two but he may well be the best GM we've had in the last 50+ years.
Anyhow, on the subject of Marner, someone mentioned that he's luckily lived up to his contract. I don't know if I agree with that but this year he did for sure and hopefully it's a sign of things to come. It was still an overpayment at the time and I really hope he understands that, puts his ego aside for the next negotiations and give us a break. I really hope Matthews does the same, sure they're great players but would do wonders for their legacy if they gave us even a little bit of a discount.