It's a question that not only grips the minds of Bulls fans, but also ignites debate across the NBA landscape.
The trouble in this conversation is that the Bulls have been plagued by injuries the past two campaigns, so assessing their worth is tricky.
While Chicago may currently have a core that can win a title, one thing is for sure: Pairing Rose with another superstar in the next few years would be an ideal maneuver. This would make the Bulls a more proven threat, and it would also take needed pressure off of Rose.
So, what's the blueprint for Chicago landing a bona fide stud, plus what needs to take place and who should they target?
Let's take a look.
First Things First
Before the Bulls can even consider who to situate with Rose, there are some matters that must be addressed. They need to first establish financial flexibility.
The unquestionable move they must make is exercising the amnesty clause on Carlos Boozer next offseason. Boozer is slotted for $16.8 million during 2014-15, an excessive number that will strain their financial situation.
As a result, there is no way to justify keeping Boozer and it would be a complete shock if he's still a Bull a year from now.
Bidding farewell to Boozer is the first step in freeing up cap space, but the process doesn't end there. Luol Deng's status also beckons attention.
If the Bulls provide Deng an extension next summer, then their chances of snatching a top-notch free agent anytime soon take a serious hit. A new deal for him would mean that the brunt of their money would be going towards Rose, Deng, Joakim Noah and Taj Gibson.
Also keep in mind that foreigner Nikola Mirotic could be brought in next summer for a mid-level deal and the Bulls will also desire to re-sign Jimmy Butler in the not-so-distant future.
There simply will be little money left over if they retain Deng, and definitely not enough to lure a marquee addition.
If the Bulls long for a secondary star, then they should be content to move on from Deng. Perhaps they make a run with him this season and then let him walk next July, or they could dangle his name in trade talks prior to then so they at least acquire something for him.
At any rate, the Bulls will most likely deem Deng expendable as they ponder their future outlook. In fact, it already appears that they're processing that scenario since they haven't aggressively pursued contract extension talks with him.
This paints the picture of what must first take place in Chicago if the Bulls desire a superstar next to Rose. Nothing will be realistic unless a couple members of their current starting lineup, Boozer and Deng, venture elsewhere.
A 2014 Summer Splash is Unlikely
Even if Boozer and Deng depart, the Bulls will still be limited in their approach.
Rose, Noah and Gibson will gobble up much of the salary cap, and they'll also still have Butler, Mike Dunleavy, Marquis Teague and Tony Snell. These total salaries alone will be around $47 million.
Plus, factor in a contract for their 2014 first round pick and a potential offer to Mirotic, and the Bulls will be approaching $55 million.
With the salary cap projected at approximately $62 million, it's improbable that the Bulls conjure up enough money to attract a 2014 free agent like Carmelo Anthony, who has an early termination option, according to Hoopsworld.com.
Quite frankly, it could even be problematic if they want to bring back Deng. He may demand more than what Chicago's willing to offer. The Bulls may be forced to merely snag a couple players for minimum offers.
Simply put: A 2014 summer splash in free agency is highly unlikely. Any hopes of the Bulls headlining the offseason with a prominent addition is misleading.
What About a Trade?
There's always the chance of a trade, but the Bulls, unfortunately, don't seem to be proactive when it comes to wheeling and dealing.
This should change ASAP.
Chicago should at least explore trade scenarios involving Boozer and Deng. The reason they must do this ASAP is because the contracts of Boozer and Deng would help construct a deal.
If the Bulls were to wait and entertain trade offers a year from now once Boozer and Deng are presumably gone, then they'd have to most likely include Noah or Gibson so that the finances would work.
One might wonder what team has an interest in either Boozer or Deng since Boozer's aging and his contract goes through 2014-15 while Deng is amid a contract year with no guarantee that he'll re-sign.
This is where Chicago's possession of a Charlotte Bobcats first-round pick is crucial. The deal is protected in 2014 and 2015 (a top-10 slot in 2014 and top-eight slot in 2015), but is unprotected in 2016. With the Bobcats showing little signs of improvement, this pick holds undeniable value.
Furthermore, the Bulls could also consider adding Mirotic to a deal. The Bobcats' pick and Mirotic could sweeten any offer mightily.
Because the Bulls have such massive assets, they should probe trades immediately while Boozer and Deng are still available for the finances to agree.
If teams such as the Portland Trail Blazers and Minnesota Timberwolves, who both feature All-Star-caliber big men in LaMarcus Aldridge and Kevin Love, struggle from the outset during 2013-14, then they could be attracted by Chicago's trade bait.
They could bite on an offer that gives them two significant future pieces (Bobcats pick and Mirotic) along with a decent veteran in the meantime in Deng or Boozer.
The likelihood is that such a transaction would involve three teams, and perhaps Deng and Boozer are both dealt.
The bottom line is that this is not the time for the Bulls to sit quietly. Their chances of acquiring a true sidekick next to Rose could best occur via trade. And it could happen sooner rather than later.
Assuming the Bulls do not seek a blockbuster trade, they will specifically analyze free agents down the road.
According to Jerry Zgoda of the Star Tribune, Kevin Love has reportedly been "enthusiastic" about the direction the Timberwolves are taking, so it could be illogical to envision him elsewhere anytime soon.
This could dramatically change, though, before he becomes a free agent in the 2015 offseason with a player option for 2015-16.
While Minnesota should be improved and could even grab a playoff berth next spring, it's doubtful they can become a contender in the next few years with the Western Conference only getting deeper.
If Love grasps that Minnesota isn't at an elite level, then he'll likely bolt for where he can chase a championship.
Is there a better option of that happening than in Chicago?
A threesome of Rose, Love and Noah would be dynamic. From a basketball standpoint, this would create a wondrous lineup.
Finances would once again be an issue, but there could be a way to figure that out during the 2015 offseason. It would be much different than in the summer of 2014.
A couple sticking points, however, could be Mirotic's contract and an extension to Butler. Those two salaries—on top of the contracts of Rose, Noah and Gibson—could unfortunately inhibit an enticing offer to Love.
The Bulls could have some major decisions in view of this. Should they trade Mirotic or Gibson and let Butler walk in free agency so they have more flexibility to go after Love?
Or could they find a way to ink Love, maintain either Mirotic or Gibson and also keep Butler? This would be perfect, but the financial layers of this could be troublesome. They're unpredictable to gauge at this point, but signing Love could mean that other core contributor(s) have to go.
At any rate, K-Love is someone the Bulls should have their eyes on, whether it be through a trade in the next couple of years or during the summer of 2015.
If they were able to lure Love come 2015 without losing numerous integral pieces, then the Bulls would be more than formidable. They'd be loaded.
The most intriguing superstar to pair next to Rose will become available in the summer of 2016.
I know, it's a long way away and, yes, I also know that the thought of Kevin Durant in a Bulls uniform is a mere dream right now. He could very well remain with the Oklahoma City Thunder for his whole career.
Let's explore this, though, because looking under the radar, this could be a compelling option for not only the Bulls, but also for Durant.
In a Comcast SportsNet interview late in September, Durant expressed praise for both Rose, his offseason workout partner, and Bulls coach Tom Thibodeau. Durant clearly respects what the Bulls are doing.
Further, there is current ambiguity surrounding how content Durant is with Oklahoma City's decision-making in the past year or so.
This can't help but make you wonder if Durant would consider joining the Bulls when he becomes a free agent. While it's a few years off, let's contemplate what could happen between now and then.
The Thunder could fail to reach the NBA Finals again because they are becoming more of a two-man team with Durant and Russell Westbrook. This could prevent them from making a deep playoff push in the West with teams like the Los Angeles Clippers, Houston Rockets and Golden State Warriors quickly emerging.
Durant could also realize that while Westbrook is a premier point guard, he is not the optimal complement. Westbrook's high energy is his staple, but it often leads to ill-advised shots when Durant should be getting touches.
A few years from now, this could be crystal clear and the Bulls could have a maximum contract spot open for the Durantula.
There is surely a way for the Bulls to configure their finances so they could chase Durant. It would likely mean losing a current core member or two, but would anyone really care if it meant they would have a tandem of Rose and Durant?
D-Rose and KD would flourish alongside each other and they would both be 28 years old entering 2016-17. They would still have quality years in their prime together.
Rose's understanding of the game would enhance Durant's repertoire and vice versa. They would foster chemistry with one another that would be virtually unstoppable.
This would be the ultimate blueprint for the Bulls: to unite Rose with another superstar.
How should the Bulls approach pairing a superstar next to Rose?
That said, it's not like the Bulls should disregard their current opportunity to contend. If they can stay healthy during the 2013-14 season, they can make noise in the playoffs.
However, netting a true superstar in the next few years is something to speculate upon.
The intangibles outlined here magnify what could be involved in this. If things fall into place properly, the Bulls could form a dynasty, with Rose and Love or Rose and Durant leading the charge.