With the trade deadline approaching, the Bulls should look at the potential to achieve any one of three or four different goals. A failure to achieve a goal isn't a failure by the front office though as frequently there's no possible method to achieve your goals. If there was then 30 teams would hoist the championship trophy every year.
Add the missing piece
The goal every season for pretty much every team is to add the missing piece that gives the squad a major boost in performance. Typically a high priced player demanding out from his present team or possibly leaving the next year in free agency or maybe a guy on a dicey contract. This year, the missing piece candidates are Dwight Howard (looks like the Lakers won't trade), Rudy Gay (already traded to Toronto), Eric Gordon, and Josh Smith.
Crossing out the first two names, the Bulls can look at Gordon/Smith and decide if either guy is likely to put them over the top or give them a considerable improvement relative to what it would cost to get them. Eric Gordon has three years left at 15 million a year and has had significant injuries virtually every season of his career.
He's an undersized SG who can drive the lane and despite excellent shooting in college has been only a pedestrian three point shooter in the NBA. He was a guy that everyone drooled over three years ago creating a sentiment that the Bulls should continue to pursue him despite having multiple serious knee injuries since then which has caused his game to seriously regress in the little time he has played on the court.
Eric Gordon's probably not worth his 15 million dollars a year when healthy nor has he shown any ability to stay healthy. New Orleans has said they're open to shopping him and because he's still young (and healthy right now) there should be plenty of interest. A Bulls package would likely need to include Luol Deng, Carlos Boozer, or Joakim Noah to make the salaries work.
I'm sure Bulls fans would fall all over themselves to dump Boozer in this deal, but New Orleans isn't saying yes to that for obvious reasons, and I'm saying no personally to anything including Deng or Noah. The team gets significantly worse if it dumps Noah for Gordon and with Deng the team probably stays around the same level except it adds more salary and far more injury risk to it.
Eric Gordon effectively has SG version of Carlos Boozer potential, and so you don't give up one of your very good players to get him 16 games after he's effectively missed a season and a half and still hasn't shown an ability to get back to 100%.
As for Josh Smith, the only trade really makes sense for Smith is Boozer for Smith, but the Hawks aren't going to touch that, so it seems unlikely something would get done. Smith is expiring, so the Hawks are likely looking for another expiring (or quality player) back and a draft pick to unload him and prep for next season.
The Bulls can't really get their salaries high enough to match for Smith in any practical way, so he's more or less off the table unless the Hawks want Boozer in which case let me help pack his bags to ensure he doesn't trip and blow the whole deal.
It doesn't look good this year (like most years for most teams) for adding the missing piece.
Adding the key role player
If you can't add the missing star then frequently you look to add the role player that you can use. The Bulls could definitely use another big man in their rotation, but they're kind of caught in big man limbo because any big man worth having will cost way more than the Bulls want to pay. I've mentioned options like Timofey Mozgov or Samuel Dalembert before, but Dalembert probably has played his way out of consideration recently and Mozgov probably isn't worth giving up an asset for.
The Bulls best bet to add a fourth big man might be to dump some salary through another trade (if possible) and then pick up one of the big men floating around on a minimum salary deal somewhere or simply wait until they have enough salary room to afford someone for the rest of the year (probably another 10-15 games or so).
J.J. Redick also fits the key role player role, and Alex Kennedy reported the Bulls had interest in adding the SG whom they signed to an offer sheet two and a half years ago. Redick is in the final year of his deal and doesn't figure to be coming back to Orlando. A move of Hamilton + Belinelli + draft pick for Redick may work for both teams. The Bulls probably send Orlando $1 million in cash as well in order to facilitate Rip's buyout next season.
Redick would considerably improve the Bulls SG rotation. Jimmy Butler would then back up the two and the three, at least temporarily, with Kirk Hinrich sliding over to play some two when Derrick Rose comes back. They'd also have three point specialist Daequon cook available to fill in emergency minutes there as well.
The move makes plenty of sense for Chicago, the question really is whether or not it makes enough sense for the Magic to pull the trigger. If you're the Bulls you don't give up more than your first rounder this summer for Redick who may simply be a rental player. There's no telling what kind of offer he'll get in free agency next summer.
Of all the trades I can think of this one makes the most sense, but it really relies on whether or not the Magic find the offer of 1st rounder in the 20s worth the trouble of trading J.J. for.
Improve the salary structure/flexibility of the team
Chicago's presently set to pay the luxury tax, and you know they'd really rather not. I don't think the Bulls have a get under the tax at any cost mentality, but I do think they have a very strong desire to get under the threshold and will sacrifice some team performance to get there.
In an ideal world, the Bulls could save money by shipping out Hamilton for nothing to some other team. I don't think any Bulls fans would mind seeing Rip go, and the trade exception earned could be used as an excuse to give up a 1st round draft pick even if the team isn't likely to ever use the exception later.
Chicago would also like to move Carlos Boozer in order to save money, but a few Boozer trades that make any sense since Chicago needs to bring back a big man in this scenario, and they'd still need to expand the deal to get under the tax unless they trade with someone under the cap (unlikely in this scenario).
The Bulls could also move Boozer to clear up long term salary rather than as a tax saving move this year and would likely love to achieve that goal too. That's where the Bargnani for Boozer rumors come from. While it hasn't been rumored in the press, a Kris Humphries for Boozer trade would fulfill the same goals of both lowering present salary by a few million and future salary by a few million next season and takes one year off the books (the Bulls could amnesty Boozer to save that year from the tax but would then still have to pay him).
A Boozer for Josh Smith trade would do much the same, but I don't think the Bulls could add enough sweeteners to make the Hawks bite.
Expect a quiet deadline
It's always been interesting to me that Bulls fans frequently lament Chicago not doing more at the trade deadline when they've actually done at least something in most year, and that something ha turned out well in virtually all of them.
Noc + Gooden for Miller + Salmons
Thabo for pick that turns into Taj Gibson
James Johnson for the pick that was traded for Nikola Mirotic
Tyrus Thomas for the Bobcats future pick
Kirk Hinrich + pick to get a shot at cap space for two max FAs
Probably a few more in recent memory, but all in all, the Bulls have generally made at least one tweak at the deadline every year, and it's always been a nice move that helped forward the organizations goals.
This year I think the most likely scenario is no trade at all. The Bulls have too little financial flexibility to make much happen.