IDK there was a real die-hard contingent defense following each moves as 'not that bad' and 'at least he is trying to win' steadfastly refusing to see the bigger picture and where this was going to end up. I don't think even the most pessimistic of us called becoming one of the worst rosters "in NHL history" but I personally wasn't surprised when it happened. I would say the biggest tool of the defender camp was to look at each move individually and be like oh it didn't do that much damage, or hey he got a few wins when he started rebuilding (like 7 years too late). The big picture was clear, and early on, but there was host of defenders and I enjoy the irony when those in that camp complain about how bad the team is currently still refusing to fully acknowledge the depths that this team sank to under Holland. Even if it was Illich giving ultimatums it's still Holland's legacy and we will never know for certain that is truly what happened because that is inner circle stuff. When Holland gets in the HOF the HOF will include a GM who built one of the worst rosters in NHL history.
I really don't get all these Yzerman is as conservative as Holland arguments. Yzerman would have been night and day just like he actually is now. I do wonder though if he would have stayed in the position if there truly was the ultimatum to prolong the streak. I don't think his continual improvement building style would have meshed with 'get in and anything can happen'. At any rate I doubt he resigns Helm or signs Neilsen, Cleary would have been off the roster and early, he probably signs Abby but for like 4 years, our drafting would have been better, promoted Nyquivst earlier, got better linemates for Datsyuk, did better than Colaiacovo/Quincey/Green, doesn't move Daytsuk's contract and we just eat it, probably executed half a dozen smaller moves upgrading players with younger and better versions, moves up in the draft instead of down.
I know there is a lot of agreeing to disagree and bygones be bygones over all of this but I still have some strong memories from those days.