It sounds to me that you are saying winning = good GM, losing = bad GM. What moves in 2010, 2011, and 2012 were you upset with?
The reason why I ask, is because there are plenty of things to criticize Holland over, but having your team go on a down slide after being contenders for 20 years is not one of them. EVERY team goes on a down swing, the fact it took us so long is an example of our FO doing a good job, not a bad one.
IMO there are only two major mistakes that Holland makes.
1) He is way to tentative to make a trade, sometimes you have to take a risk.
2) He puts too much value on vets. I agree that vets are crucial as with no vets you become a joke like Edmonton this past decade. But Holland needs to sometimes let vets walk (ie. A Helm situation) and give a kid a shot instead. I am just using Helm as an example, I actually really like Helm, but Holland just keeps signing vets when he should be allowing kids to play. Plus, having all vets keeps you at the cap, and keeping you at the cap can restrict your ability to pull off certain trades.
The second part is just untrue. A GM's job is to acquire and retain high end talent, and place them with good secondary talent. Holland did that for a very very long time. To say that the talent he acquired and retained masked him being a poor GM goes against the fundamentals of what his job is. The fact that he was able to acquire Datsyuk and Zetterberg, and then get them to stay along with Lidstrom their entire career's is part of what made him a great GM.
There is no denying that Holland has dug himself into a hole, if he is still a good GM he will climb out, if he's not he won't. Simple. Unless of course the players he acquires moving forward do really well and mask his abilities again