The Bulls are just a complete mess from top to bottom and it goes way beyond the saga that has been Rose's career.
I've alluded to it in the past but the organization is rotten from top to bottom in terms of the relationship that Reinsdorf has with the front office, and in turn the relationship the front office has with the HC and the team. The main reason for it is that there is an overarching philosophy within the organization that "organizations" (see: the GM/front office executives) are what win championships, not players, and Reinsdorf is willing to have complete unwavering faith in his front office executives no matter how bad they fuck things up. This is the same organization that fostered a toxic relationship between then GM Jerry Krause and literally the GOAT player/arguable GOAT HC because of some horseshit ideal that "organizations" are what win titles and not players.
I can't even believe that type of arrogance and tone deafness exists.
Sure, the organization drafts reasonably well (Butler, Gibson and Mirotic at the end of the 1st, Noah at the back end of the top 10) but is that really that much better than above average league wide over a 10+ year period?
If they hadn't lucked into Rose this team would've been nothing but a 2nd round and out team for damn near 15 years, and yet they don't even consider making changes at the top?
And even with the fortune of having a guy like Rose, when did this team ever complete a moonshot to try to win it all? Their best shot was what, Pau Gasol? Come on.
They are never able, or seemingly never willing, to close the deal on top free agents or big trades. There is always some nebulous "future plan", the 2010 plan for LeBron that netted Boozer, the 2014 plan for Carmelo that netted Gasol and an extreme, almost pathological reluctance to trade "young assets" until they are lost for nothing (Deng, Asik, even going back to Ben Gordon).
The whole thing with Rose has been nothing but a crutch for the front office to "sit tight" so they can "see what they have", an excuse for them to not go outside of their comfort zone. Well, even if/when Rose is gone, I highly doubt much of anything changes. You'll still have a risk-averse front office that is more than happy to sit on draft picks while being a 45 win, 1st or 2nd round playoff team each year.
And I'm not even going to get into the complete ridiculousness that was the hiring of Fred Hoiberg, a guy who doesn't have any kind of actual NBA coaching ability and was only hired because he is boys with HOF idiot Gar Forman. Of course Forman is the reason that Ron Adams, one of the best assistants in the league, was fired because he got in a pissing match with Forman (of course the organization will always choose the front office executives over the coaches or players) over Forman not being a good evaluator of talent with regard to Forman wanting to take Marquis Teague over Draymond Green.
We see how that one turned out.