I get why teams like Calgary hold on to Bennett for so long...because shit like this happens. Not Calgary has egg on their face. That being said, I don't know if Bennett does anywhere else what he's doing in Florida. It is literally the best scripted situation for him.
Yeah, but do they have egg on their faces? They held onto Bennett for 400+ games, through a variety of coaches, through 6+ seasons. And their highly touted 4th overall pick never fulfilled his offensive promise stuck in that situation. Because of the linemates or whatever the reason was, it just didnt happen. And despite hanging onto him that long, they still turned him into a couple of second rounders, a return most people thought was still pretty high.
I agree with your point about Florida, it was a great situation for him to walk into. But my point is that he might've blown up in a lot of places after a trade, because it seems it was more about getting out of Calgary than it was finding the perfect landing spot. In that respect, no, I dont think Calgary should be embarrassed or rueful at all, especially when nobody can say they gave up on him "too early". And in a world where Gaudreau was taken in the fourth round, Florida's second rounder might net them a player who is a much better fit on the Flames.
In the end, this is a much better result,
for everyone, than Sam Bennett staying there until he's 27, considered a complete bust, and becomes a journeyman to recover what's left of his career. In that sense Calgary gets very little, the player gets no second chance, and no other team in the league benefits.
The flipside is a team giving up on a player way too quickly. Washington not knowing what they had in Filip Forsberg when they shipped him for Erat is one. Another is the Strome situation with Chicago (now realizing he didnt have much time there at all...but Arizona seem uniquely good at screwing up their high draft choices). In cases like that, egg their dumb asses.