Personally I think that you need to manage your organization ruthlessly for the betterment of the team in the long run.
To that end, regardless of where you are in the standings, you need to capitalize on assets if the market is compelling. To the extent the market is not compelling, yes, it probably makes sense depending on the asset to stay still (but not always, such as the case with Vladar, IMO).
Yes the above might mean you forego a Stanley Cup chance potentially in the short-term, but ultimately over the long-run you will have more chances and higher probability chances at winning, and winning over an extended period of time.
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