This will be the hottest of hottest takes. It will annoy many of you for so many reasons and I can completely understand all of them, if raised.
With that being said... Kiprusoff for 2nd (Vlasic) was the worst trade Wilson made, imo. Not because of Vlasic, who has been a terrific servant of the club, or even the return value, but because we banked on the wrong guy who I think would have set us over the top during our peak years.
I am not going to criticise a 'go for it' trade at the deadline - most won't work out, but it's the home run move that - if it pays off - will be remembered. Also the assets moved are kinda meh quite often.
Kiprusoff had one uninspiring statistical season and we gave up on him. Sharks were terrific in that 2005-10 spell and, as much as I love Nabby as a franchise legend, Kipper was later a Vezina-quality no.1 - the one thing we missed. Missed opportunity, imo, and that's why it's the worst trade above all.