Yeah, usually other organizations will fire their "buy-now get-success" GM after the "window" is gone and sign a puppet-GM to do those "horrible sell-trades" when they rebuild and stockpile talent. And then sign a "buy-now get success" -GM again when the new core in on a rise. Calgary Flames is a good example of it. They were bad and Feaster got the hate, but at same time they stockpiled great kids pretty nicely. Now they are on a new rise.
Red Wings are doing the whole operation with one GM. Period. No firesale, stockpilling young talent again like 80-90s and keeping the team at playoff push. This is definitely the hardest way and toughest challenge for any GM to do, and I think Ken Holland is the only guy who can accomplish it.
He has already won a Stanley Cup with prospect stockpillin. 97&98. He did won 2002 Cup with money and and he did win 2008 Cup when there was a cap. Any other GM hasn't been able to win multiple Cups in this kind of different circumstances and maybe he just wants to finish his career winning one more Cup with this kind hardest possible challenge.
There's so many guys hunting their first. Kenny wants to win his fifth Cup with a style.