Many organizations also rationalize poor decisions by inventing limitations that may not exist if they just went to the fanbase and honestly explained their decision-making. Maybe there was ownership interference as well...who knows but they should have stuck to their guns regardless of whatever history they're trying to overcome. Is the ultimate goal to finally win a playoff series or the Cup? Fact of the matter was/is it's hard to win when some of your best players are halfway out the door. It's a credit to them that it hasn't been a massive distraction up until recently. But even if we go along with the strategy, the execution was also pretty questionable. They did need a center but did they need to go all-in on Duchene and agree to not just give up one first rounder but also potentially a second one should they re-sign him? That's a poison pill type agreement. Was Dzingel really the player they needed vs. one of the many other options? The same goes for McQuaid, even if the D market was pretty thin.
The mix looks very off at the moment and some of that's hindsight but where I'd mostly center the decision-making is on whether their younger core group is deep enough to be so aggressive regardless of what may happen with UFAs. I think the answer on that has always been no, esp. with the season Wennberg is having and that they don't have much in the way of real high-end talent in the pipeline (although it's not altogether terrible). Even with a bunch of cap space this is probably a team that will need considerable alterations and retooling over the next couple seasons, particularly should they miss the playoffs. I'd bet on that vs. MTL/CAR and the next week or two may be all it takes to sink them mentally.