Kind of interesting that both of Hollands 'disciples' - Yzerman and Nill are ranked (well) ahead of him - #1 and #6 respectively.
In fact of the top 10 'ranked' GMs, Only 2 (Nashville and SJ) have been with their team for longer than 6 years.
You often hear about Coaches having a 10 year limit on being effective, as their message can often get stale over time and players tend to tune them out. I think that is also possible with GM's (to a lesser degree), their philosophy can become stale, and often times they rely on 'whats worked before' and don't change with the times.
Its very easy to get tunnel vision as a GM, and this seems to have been the case with Holland...he was a master at finding the right fit of superstars who could actually play together as a team (its not as easy as it looks - see the Yankees), and he had a knack for surrounding himself with a staff full of people extremely good at their jobs (scouting in particular), additionally, he was/is extremely good at retaining his players. Very rarely do you see a player leave the Red Wings (that the wings actually wanted to keep) - he is loyal . This used to be a positive attribute as it showed other players that once you're a Red Wing, they will take care of you, and there was no salary cap so who cares if its a slight over payment - hes 'our guy' now, and the Wings treat their guys better than any other organization.
The salary cap has honestly messed up Holland something fierce. yes he won the cup in 08 but that team was almost completely built prior to the salary cap era. He has tried to adjust - but seems to have overcompensated in some aspects. He used to deal young players and draft picks without a second thought, he now hoards them like they are all the holy grail, and is petrified of trading away a potential 'stud' for an established vet.
One area he hasn't changed at all in is loyalty to his players. He still signs guys to very generous contracts (this off season being a prime example), and makes sure they get playing time/a roster spot, even thought there are more talented/cheaper players in the AHL chomping at the bit to player at this level. This is awesome when you have a team full of studs, as you will most likely keep them around, but when your team is full of average NHLers, you need to be cut throat and fearless when it comes to choosing who to keep and who to let walk away.
I am not saying that Holland cant be successful again, but history is def. against him suddenly changing his ways and making the necessary roster moves that this team needs. I think a change of scenery would be better for everyone involved...