I am much more of an optimist than most people on this board.
My "optimistic" point of view after the last few games is this:
Sell. Trade the pending UFAs, call up players from Wilkes for the rest of the season, and then, if you still want to try to make something out of the remainder of the Crosby/Malkin years, use the assets you get from those trades to reshape the roster at the draft.
The Pens are not going to be able to retool in this year's draft. They simply aren't falling far enough to get into Bedard contention, but they certainly could use picks accumulated from other teams to acquire players that better fit with where the front office wants to see the team go.
And yes, it should be a different front office staff making those moves at the draft.
And that would include allowing the new front office staff to choose their own coach staff, instead of having to retain the current staff, as well.
They don't necessarily have to slide all the way back into a new Dark Age, given that Crosby and Malkin are still both playing well, and at reasonable costs. But they desperately need to re-shape the roster at this point. Or else another Dark Age is inevitable, even with those two continuing to play well.
