Because the argument was made that some rebuilds never get anywhere. Edmonton and, until recently, Toronto, seem to fit that bill, do they not?
If you think Holland is a great GM, then that mindset makes a lot of sense. It's when people point at Edmonton to say "rebuilds are a bad idea, and might never work at all!" and simultaneously want to pretend that "of course we'd be better with all those #1s!" that it gets pretty disingenuous/hypocritical.
Either Holland is the bee's knees, and it doesn't matter if we started rebuilding in 2009 or today, it still would've worked, or Ken Holland is absolute garbage, and it doesn't matter if we'd started rebuilding in 2009 or today, because either way he, like a number of other GMs, isn't capable of making it work, and we're in limbo till he goes to Seattle no matter what.
You could also ask why a coach is so un-motivational and bad at player development that he still has players who only give 50% and won't buy in.
But really, I just want some consistency from both sides. If you believe Holland is X, then believe it.
And I know I personally have. He's a great GM.
The people who say "oh, you shouldn't rebuild because it might fail" are stupid. The people who say that Detroit needed to tear in down in 2010 because if you're not first, you're last... are stupid.
The truth has always been somewhere in the middle. My own personal feelings on it is that "rebuilds are silly" because anyone selling you a 5 year plan to get better is trying to earn them 5 years of security. The Wings have failed because they have only gotten good players out of their picks not great ones. They failed because they weren't as proactive in finding roster replacements (can't replace their talent, but can find players who can play the role) for Lidstrom, Rafalski, and Stuart.
The failure isn't that they declined to trade their veteran roster players for draft picks. It's that they largely whiffed on the picks they had in the late 2000s.
McCollum, Smith, Kindl. That's three first round picks that they got NOTHING out of. Smith was a below average #5, Kindl was a terrible #6, below average #7, and McCollum was hardly an AHL goalie.
The second round picks they had...
Landon Ferraro - garbage
Joakim Andersson - garbage
Tomas Jurco - garbage (he may not have been if his development wasn't screwed up)
Nastasiuk - garbage
Xaiver Ouellet - replaceable garbage
Ryan Sproul - garbage
Third round picks
Mattias Backman - garbage, traded to Dallas and he went home
Mattias Janmark - garbage, traded to Dallas, got 30 points on their high powered top line.
traded a 3rd for Dylan Sadowy - garbage
That is a list of 12 guys who have contributed nothing to the success of the Detroit Red Wings that were taken in a reasonable slot in the draft to expect an okay hockey player. This didn't come down to having a few more bites at the apple. It came down to terrible scouting. The Wings had picks, they just swung and missed on them.