Late 1990's to the early 2000's...Even with all that $$$, and a all-star roster the team failed to make the playoffs for 7 seasons in a row.
EDIT - I know I'm dating myself by going back to previous seasons...Just that I feel Stevie Y is by far the most deserving.
I agree. I'm mostly just being a jerk. I don't want the competition to succeed at all. Even Stevie. I just can't cheer for the GM of the team that dealt the Wings their most recent playoff loss. Same way I won't be hoping for Babcock to win the Jack Adams anytime soon.
Ken Holland has been with the organization for 30 years. 18 of which he's been the GM. He started as as scout, then the director of scouting, then the assistant GM, then the co-GM, and then the full GM. It's not a coincidence that he was hired just prior to the Wings beginning an epic playoff streak.
To try and dismiss his contributions to the organization as anything less than profound would be an absolutely gross understatement. He's been more important to this team's success then any other individual.
If you hire a GM from outside the organization, you can argue he's riding coattails. But it's a little hard to say that about a guy who's been a member of the Red Wings longer than Steve Yzerman and Nick Lidstrom.
To a lesser extent, this is true of Stan Bowman as well. Sure Tallon was the GM before him. But he started with Chicago in 2001 when they were a garbage team. Unless he was just standing around playing with himself for 8 years he likely contributed to their assent. Is he entirely responsible? No. But he's contributed from the bottom up.
Yzerman doesn't deserve much credit for that first conference finals appearance as he had just come in from outside the organization and had been with the team for less than a year. But he deserves credit for every single other success they've had since.