Big elephant in the room. We have not won a cup in seven years and haven't been to a final in six. Scotty Bowman leaves our organization and makes an instant impact on the Hawks. They have won three cups since he left. I think the organization has drifted from a philosophy that helped build a winner and I would like to see us return. The philosophy is hire the best and let them work. We poached the Islanders chief executive when they were winning cups and then we poached Scotty not far removed from Pittsburgh's run. Scotty left and then Steve Yzerman. I know the conventional wisdom is that we couldn't keep them which may be true. However, I hope the front office is working to figure out ways to bring these men back. In short, we should begin once again work to bring the best brains in the NHL back into the fold not see them leave.
In this age of player parody, front office brain power is emphasized and we let two extremely talented men leave the fold.
You probably could include Jim Nill as well but his impact hasn't been nearly as large as Scotty's was.