Very good point - and my MAIN problem with Snow: asset management!
Unless you have a very doggone good reason to believe that you're current club is going on a long and competitive playoff run, then any upcoming UFAs (of value) you can't or don't want to re-sign before the trade deadline needs to be moved. An asset cannot simply be allowed to walk and become a non-asset.
I know some don't like that point of view. I know some don't agree with it.
But it leaves your club in a position of strength from a business standpoint at just about all times.
Hindsight is 20/20 for sure and looking back, the team was absolutely naive and mistaken for not moving Tavares. During the moment though, I was convinced that he was re-signing (as were they apparently) so I was of the opinion that we shouldn't move him. The team would have absolutely taken crap for trading/marketing him, but we would probably have 2 more 1st round picks coming up. It may have even been Ottawa's as they clearly would have preferred Tavares over Duchene. And telling him that he was going to be put on the market would probably have gotten him to sign - given his school boy ass a wake up call.
This debacle will probably change the way they do business going forward. Other teams as well. If you don't get that absolute commitment from a player (meaning the extension signed), you need to explore moving him. It worked out for the TBL with Stamkos but obviously we got screwed.