The decision to keep Giroux/Voracek/Schenn/Couts here, while simultaneously not fixing the defence or the goaltending. It made sure this team would be too bad to bottom out, but not good enough to compete. The team either needed to put talent around the forward core in order to compete, or sell off everything and rebuild from the ground up.
They decided on neither.
So now waiting for the team to draft their own defenders, the forward core would no longer be in their prime. It doesn't help that by the time everything was supposed to fall into place, Chuck was the GM and had no idea how to take the team from rebuilding to a contender.
I still hate the decision all those years ago to go full steam ahead on rebuilding the defence from within while our forward core was ready to compete. At best, it gave the team a 2-3 year window in which the dmen we drafted we're experienced enough, and the forwards were still young enough to be cup caliber. Assuming it worked out perfectly, and all the dmen we drafted actually panned out (which of course they didn't due to awful player development), it gave this team a very narrow window of competition, which always felt worse than rebuilding for a shot at a 5+ year window later down the road. The risk of even one thing going wrong during this window would have crushed this team's chances (which we can see now come to fruition), and would leave this team in cap limbo with players at all stages of contracts. Old vets locked into long term deals. Young players needing new contracts. Team not good enough anywhere in the lineup. No hope of contending, and scorched earth rebuild the only option left to them.
I always thought the choice of going for the 3 year window over a full rebuild was the wrong choice, and after seeing the team royally f*** it up and bungle the whole thing, it has made me even more cynical of the route they chose. Maybe it would have worked out better if the people in charge weren't doing their best to run this team into the ground, who knows. But a strategy that has to assume the people running the flyers be competent at their job is doomed to fail before it even begins. The 3 year window was never going to work, because it meant management would have had to be good at their jobs. It felt it was the wrong choice then, and the decision has aged like milk since.