These trades aren't happening. This organization is paralyzed by the restraining aspects of Prospect Theory
https://www.behavioraleconomics.com/mini-encyclopedia-of-be/prospect-theory/
Not winning the Cups is not prioritized over having a CHANCE to win the Cup. So the bigger loss is perceived as not making the playoffs no matter what they say. Hence the big moves after the last playoff miss, and the constant "this is fine, we just didn't do X like we should have" background message through little changes after playoff disappointments.
This means the organizational attitude is always "anyone can win in the playoffs", which may be true in the sense that seeding seems to be less important in the current format, or else they for SOME reason believe they keep putting together
playoff-ready teams that inexplicably fall short. Since they've had this "just get in" attitude prior to the changes to playoff format I'm inclined to believe they see themselves as viable playoff contenders based on regular season success, and think that "anyone can win" because they don't recognize what separates winners from losers in the postseason. Which means they don't understand what it takes to go deep and will keep repeating these mistakes while making tweaks.
If failure was defined as anything short of winning the Cup in Y years then the script would flip and the loss aversion would change to risk taking. We heard about this "window" for the last 3 years but that's likely going to be another half-measure solution and just more talk.
-Dr. g00n