The decline and fall of the Red Wings isn't on Ken Holland... it's on the NHL for changing the rules.
The NHL is designed for ALL teams to decline and fall after their 1st overall drafted players/core age and decline. It's going to happen to Chicago, Pittsburgh, then Oilers, TMLs... all will rise and fall. That's the design of the NHL.
We see less blockbuster trades, less GM creativity, less exciting FA frenzy, less exciting trade deadline moves.
The most entertaining part of the nu:NHL is teams signing mistakes for a $100 million only for them to run off to the KHL.
As far as Ken Holland goes, when putting the actual circumstances in context, the NHL stacked the decked for the sole purpose Red Wings would fall. The conundrum is fans, who pay nothing, sit in their favorite lazy-e-boy and post on random hockey forums and blogs to talk about how they would do things, and their way is the only right way, while disregarding the actual $$ and politics from the factor.
NHL zapped front loaded contracts and it hurt the Wings for legally signing contracts they are now being punishing for.