Ira Winderman came out and said it -- that the price the Bulls would have to pay for Dwight Howard creates problems similar to those of the Knicks. That any price that ends with Howard as a Bull is a long-term net positive is not a self-evident claim.
The common counter-point is simple -- that the Bulls' status quo is to consistently fall a step short, barring elements out of their control (health of the Heat and aggressiveness of other front offices playing catch-up in the meantime).
Winderman's point is a simple master-of-the-obvious that ought not be marginalized: if the Bulls can't essentially re-build a team to be better with Dwight than without him, paying the high price is a waste:
The point being that all-for-one can work and the Bulls, with Derrick Rose and Dwight Howard and anyone, would be as good as anything in the league this side of the Heat.
But that's the rub, they just might be that right now, anyway.
Start peeling layers from arguably the league's best chemistry and the Bulls wouldn't be the Bulls, at least "these" Bulls anymore.
It is one thing to unload Carlos Boozer (no one is taking), another to start pushing chips such as Joakim Noah, Luol Deng, Taj Gibson, Omer Asik to the middle of the table.
The Knicks went all in last season and this season appear lost because of it.
But the Bulls are ahead of both those teams already, and in cashing in for Howard could cash out on a good thing already in place.
Nuggets GM Masai Ujiri gambled hard on taking so long to trade Carmelo Anthony. He risked the price he could demand plummeting out of the universal knowledge that the Nuggets were in a dilemma of trading their franchise player or losing him for nothing. When the market rationale was to not let such a scarce amount of trade partners regressively lowball their offers to prey on desperation, Ujiri aggressively shopped Anthony to any and all suitors to field competitive offers that actually drove up the price to acquire 'Melo; and the Knicks paid a huge price on what was supposed to be an easy-breezy take.
Now, the Knicks stand at 8-14 with 'Melo, 22 games into this season, after starting 13-9 in so many games without him last season. Though the move isn't a lateral one, as the Knicks had nothing for which to live but mediocrity before 'Melo and now have an attractive destination and Tyson Chandler, the Bulls' status quo has much higher potential than those pre-'Melo Knicks. And, therefore, more to lose with a lateral move that risks handcuffing their wiggle room to build upon a Bulls team with Howard.
I can only plead humility on this topic of conversation and say that I'm not sure what the correct decision is for the Bulls. And this is because there isn't any reason to believe the already aggressive Magic GM, Otis Smith, won't take a page out of Ujiri's book and drive a bargain so tough to force no team to easily press that button and execute a deal.
There are ways for a Boozer or Noah deal to work with other pieces, including the Charlotte draft pick, to match up with Howard's salary in order to make a favorable deal in accordance with the league's regulations. But the Bulls aren't the only team in the NBA; and the other suitors are in greater states of disarray, slowly trending downward, or more pieces short of contending (Lakers, Nets, Clippers, Mavericks) that they're in less risky positions to make better offers than the safer ones from the Bulls.
Add in that it's pretty uncontroversial that Smith will demand whoever takes Howard also take Hedo Turkoglu and the money adds up in ways that the pieces necessary for the Bulls to execute a deal re-creates the Bulls into an unknown element of the league. This compared to being a known contender right now.
That said, the conventional wisdom in the NBA is that you get the best player you can one at a time, minimizing the amount of players you absolutely need to over-perform in order to contend for and win a championship. The Heat, Knicks, and Clippers are operating that way; and they're all better off now than when each team began these aggressive missions, while the Cavs, Hornets, and Raptors are struggling for relevancy.
Smith sees all of this and knowing that he can be the Nuggets will keep him from becoming the Hornets. And that equals a sell-it-all offer from anyone to acquire Howard.
Also, think of what the team who acquires Howard will be. Wouldn't they pretty much be more like the Knicks than the Bulls would? So who cares if the Lakers further deplete themselves for Howard; or the Nets give more up, adding to what they already gave up for Deron Williams; or the Clippers get more dangerous on paper with Vinny Del Negro still coaching them; or the Mavericks get him without coming any closer to solving their age problem, assuming that Smith is looking for players on the other side of 30? Do any of these scenarios potentially threaten the Bulls, compared to taking on the risk of paying a high price for Howard themselves?