Let’s get this out of the way right now, Dwight Howard will either sign an extension between now and the NBA Trade Deadline, or he will be dealt. Orlando would be extremely foolish to try and roll the dice that he re-signs with them, when all signs point to him moving on. He recently decried that he would be open to moving to the Chicago Bulls, so let’s explore that a little further.

Why It Makes Sense

Bill Simmons was banging the drum two years ago for LeBron James to go to the Chicago Bulls. His theory was that if LeBron cared as much about winning as he claimed, that was the best place for him. There is no reason the same doesn’t hold true for Dwight Howard. Howard wants to play in a “big market”, whatever that really means is up for debate, which probably leaves only a handful of teams in the picture: both Los Angeles teams, New York, New Jersey, Dallas and Chicago.

The Clippers just traded for Chris Paul and in all likelihood will be committing to him and Blake Griffin. It’s unclear whether they have the trade parts to get Dwight, and might not have the money to sign him as a free agent, but he’s got to be intrigued with that team. New Jersey might have the parts, and could lock up Deron Williams as well, but the supporting cast there is somewhat weak. New York has their big guns and are almost certainly out at this point unless they can find a taker for Amare. The Lakers could find a way to make it happen, but that team doesn’t seem on the upswing unless they plan on landing someone else like Deron Williams. Dallas is in a similar situation, with mostly aging stars, but they still have Dirk.

Meanwhile, the Bulls have the best young point guard in the NBA, a power forward who can face up, a selfless wing player and a veteran two guard. It maybe too easy to say, but with Dwight Howard, the Bulls don’t lose to the Heat in the 2010 Eastern Conference Finals. With no low post offense last season, the Heat committed to shutting down Rose, and succeeded at suffocating him at times. It would be impossible to double Rose and contain Howard without leaving virtually everyone else wide open. The Bulls are already a top 5 team, and (hopefully) wouldn’t have to give up the farm to get Howard. It makes sense for everyone involved.

What It Would Take

The good news for Bulls’ fans is that there are plenty of pieces Chicago can offer. Any trade would almost certainly involve Joakim Noah, for multiple reasons. First off, Orlando doesn’t have another true center on their roster and would have to replace Howard. Also, the Bulls wouldn’t need Noah with Howard. Noah’s contract would also be needed to make the trade valid, as salary gaps need to be filled. It’s also likely that the Bulls would have to include Taj Gibson and probably Omer Asik as well. Both are young and both play hard. These are the kinds of guys teams want. Gibson is probably already good enough to start for most teams and Asik may never be a full-time starter, but he can give 12-15 quality minutes off the bench. Obviously some picks would have to be included as well, but whatever these picks are, it’s worth it.

There is another scenario though, that could make thing’s tricky. At the moment, Orlando is stuck with Hedo Turkoglu’s bad contract through 2014 and would certainly love to be rid of that without having to use the amnesty provision on him. They could “force” a team to take Hedo along with Dwight, which would bring the included salaries up to around $29 million.

This would make it difficult for the Bulls and would likely leave them with two options. The first would be to also include Kyle Korver, Ronnie Brewer, and CJ Watson in the trade. That would be enough to even out the salaries, and since all three come off the books at the end of 2013 Orlando would basically free themselves of Hedo one year early. The downside to this is that it would literally gut the Bulls entire 2nd team.

The other (and probably worst) option would be to include Luol Deng. Deng probably has the most trade value outside of Gibson and Asik and would be the most useful to Orlando, or potentially a third team. If Orlando could acquire Noah, Asik, Gibson and a slew of draft picks from both the Bulls and a third team, they would be esctactic. It would be interesting to see if a team like the Hawks, Clippers or Lakers would get involved if Howard wasn’t coming to them. It’s even possible that the Magic would be OK with paying Deng since he is an upgrade over Hedo.

This last scenario is likely a bit of a stretch, but it’s at least a possibility.

What It Would Look Like

Just acquiring Howard for Noah/Asik/Gibson would leave the Bulls in an amazing position. The starting five of Howard/Boozer/Deng/Hamilton/Rose would easily be the best starting five in the NBA immediately. Korver/Brewer/Watson would continue to provide depth at the 1-3 positions, but would have to find depth to replace Asik/Gibson. This is likely easier said than done, but Howard wouldn’t need to be removed at crunch time the way Noah sometimes was, and if Boozer isn’t the only option down low, he might be able to play more minutes as well. Still this void would have to be filled somehow.

If the trade for included Turkoglu, but not Deng, the Bulls would completely gut their bench, but still have the same starting five of Howard/Boozer/Deng/Hamilton/Rose with Hedo as the 6th man. A solid one through six to say the least. Things would drop off considerably as the team relied on rookie Jimmy Butler and John Lucas III (who has played valuable minutes so far this season), as well as fan-favorite Brian Scalabrine as the 2nd team. This is likely enough to survive the regular season, but there would have to be some depth added for the playoffs.

If Deng were included instead, the team would still look considerably different. The starting five would then likely be Howard/Boozer/Hedo/Hamilton/Rose, with a bench of Korver/Brewer/Watson/Butler/Lucas/Scalabrine. Much like the trade for just Howard, front court help would be required to make it through the playoffs.

In either of the first and third cases, the hope would be that some veteran(s) eager for a ring, would be willing to play for cheap to make a run, at least in 2012. With Korver, Watson and Brewer all coming off the books at the end of 2013, the Bulls could have a bit of room, or expiring contracts to use to strengthen their bench.

Why It Won’t Happen

The biggest roadblock is that the Bulls trade chips aren’t that valuable. Joakim Noah hasn’t taken the next step and has four more years after this season left on his contract and a hefty rate. Assuming that Dwight Howard is gone at the end of the season regardless, Orlando will likely either want just expiring contracts and draft picks, or some younger, cheaper players. So Noah probably doesn’t make a lot of sense for them. It’s possible that a third team could help solve this issue, but three team trades are hard.

Wrap-Up

In all honesty, I don’t think the Bulls will be able to pull this off. Even dumping Noah’s contract won’t be enough to offset the contract they would have to sign Howard to, as well as finding a way to also have a bench deep enough to win a championship. I am not sure what Jerry Reinsdorf’s feelings are regarding the luxury tax, but I am guessing he wants to try to avoid it as much as possible.

An absolute perfect world would have the Bulls finding a way to trade Boozer and Noah for expiring contracts, sign Howard as a free agent, and roll with Howard/Gibson/Deng/Hamilton/Rose/Asik/Korver/Brewer/Watson all the way to Finals. But that’s even more ridiculous than the other scenarios.

Instead the Bulls probably can just root for him to end up in Dallas or with the Lakers, where hopefully there wouldn’t be enough talent to get him to the NBA Finals, and thus never being a roadblock to the Bulls’ success.