I'm on the trade at deadline team if there is no extension in place...Unless you are currently sitting as a top 2-3 team in the entire league, I'd favor the asset management approach. If you are a Colorado or Tampa, for sure, keep them and see what happens.
It is obviously something easy with hindsight and hard to decide in the moment, but I think you'd be better set up long term if you consistently signed guys early, and dealt those that were reluctant. I'd make this very clear to the players too, no surprises come the deadline.
I do understand the opposing viewpoint, but I think the Cup is such a hard to win trophy, with a lot of luck involved that you need to maximize chances over a long period of time instead of hope that this one special run is the one to do it at the expense of longer term assets.
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