those moves were made in the context of a roster that had THREE hall of famers, two scoring champs and a multiple vezina finalist, all three of whom finished no lower than second in hart trophy voting; THREE selke-calibre forwards; FIVE top three dmen (ehrhoff, edler, bieksa, salo, mitchell/hamhuis); EIGHT 25 goal scorers (sedins, burrows, kesler, samuelsson, raymond, demitra/torres, sundin/higgins)
of course you trade draft picks to try to put the team over the top
the glaring mistake there, however, was the alberts trade. seidenberg was available from florida and he and ehrhoff had proven chemistry, but gillis cheaped out and went with alberts instead. instead, boston got him for basically a smaller version of the same package that gillis sent to florida for ballard a few months later. i think he learned his lesson which is why he went completely over the top into the 2010-'11 season, sending all those shoulda-been-seidenberg assets to florida for ballard, then signing hamhuis anyway (making it SIX top four d), adding malhotra, adding torres, then at the deadline grabbing higgins and mad max.
first, horvat is FIRST in playoff goals.
my buddy managed an establishment that gillis would go to regularly, like several times a month. i'm told gillis was friendly with everyone, talked about the team when appropriate, way nicer than certain other guys on the team and many other regulars. so if he acted like a prick in a restaurant you were in once, i can report that he at least isn't an asshole in every aspect of his life.
but anyway, the answer to the OP is hiring gillis as a GM is a very expensive proposition. because he was incredibly successful as an agent he flat out does not need the money and wants to do things his way. that doesn't just mean autonomy, that means he gets to spend way more money than most owners are willing to spend trying to get every competitive advantage. and it's not just spending all the way to the cap and burying/buying out bad contracts when possible, gillis hires staff, he funds studies, he even built a new facility for his players. i know he took a meeting with florida, but i don't think he's going to work for organizations like them or arizona.