Given the lack of top 3 picks combined with being at a big disadvantage Salary wise, JR did pretty well. I sometimes think we're a bit spoiled in what we expected vs. reality.
Looking at comparable franchises, I'd say the team has done fairly well given only 1 top 3 pick. Tampa, Nashville, Columbus, Florida, Atlanta, Phoenix. Of those teams, the only other I'd consider trading places with would be the Lightning, who really have had a very similar path.
The difference being, their bad years, they had the sense to stink so bad, they got 2 #1 overall picks, and 5 top 3 picks.
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In the end, it comes down to margin of error. There just isn't one for these franchises in most seasons, and it shows in the results.
I've always felt that he's put the team in a position where if things break their way, things could go very well. But they rarely have broken in that way. Whether it's roster obliteration from injuries, missing out by 2 points, or a lack of production from sources that reasonably should be expected to produce.
Trades and Signings, I've actually liked JR's maneuvering for the most part. Drafting will always be the question mark on his resume. Just the complete absence of organizational help outside the first round (and Justin Faulk) stings. That's a big source for the safety net for when you do catch a couple bad breaks, and the team has been playing without a net for as long as I can remember.
People talk about the development in the AHL, but it could just be that the guys aren't NHL material too. It may not be a matter of development, as much as the guys just don't end up having what is needed to make it.