If the Flames were not a particularly good team this year, and had little chance to contend, absolutely they should be trading Weegar if they can't sign him to an extension. better to recoup value and wait for a better time to roll the dice.
But they are a contender, so they need to keep him and see what happens. Now, the odds are that they will not win the cup. That's the odds for every team. But that's the cost of contending. At some stage you need to hold your cards and see how it goes.
There is a reason why Huberdeau and Weegar were obtained relatively cheaply. They were older players in the last year of their contracts who needed huge extensions. As good of players they were, that decreased their value. And while Tkachuk was in a similar place contract wise, he was a very young player who would agree to an extension. That increased his value immensely. Florida decided that they wanted to extend their window for a number of years, as I assume they knew that they would not be as good this year with the trade.
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