That question, more than anything else, will define the next 12 months for the franchise.
All three of the Heat stars possess early-termination options in their contracts, which would allow them to become unrestricted free agents following the 2013-14 season. Opting out would make plenty of financial sense for each, as they'd likely be able to secure (at least) an extra two years and $40 million more on their contracts.
Because there's a clear financial incentive for James, Wade and Bosh to exercise their early-termination options, Miami likely won't be able to convince them against doing so. That means if the Heat fall short in their quest for a third straight championship, it's entirely possible that this will be the last go-around for Miami's Big Three.
Here's what the team needs to do to prevent that nightmare from becoming a reality.
Convince D-Wade and Bosh to Take a Hometown Discount
When James, Wade and Bosh originally decided to unite during the summer of 2010, each star opted to leave roughly $2 million per year on the table. Instead of signing for the maximum six-year deal ($123,658,089), Bosh and James signed for $109,837,500 while Wade took $107,565,000, according to Basketball-Reference.
Even now, such a concession remains a virtually unprecedented move for players of their caliber. James Harden, for instance, left a veritable championship contender in Oklahoma City because he refused to take a similar discount.
The Heat can't necessarily bank on LeBron being so generous during these upcoming contract negotiations. He's backed up his slew of regular-season MVP awards with a pair of championships and Finals MVPs, making him the undisputed best basketball player on the planet.
That means Miami must convince Wade and Bosh to agree upon a major pay cut.
The league's latest collective bargaining agreement makes it effectively impossible for a team to sign three players to maximum-level contracts at one time. All three players, if they decide not to opt out, will each earn north of $20 million in 2014-15.
Let's assume that LeBron agrees to a contract that starts with a $20 million payday in 2014-15. If Wade and Bosh additionally pursue $20 million each, the Heat would be nearly capped out with those three players alone.
Once you add in cap holds for other roster spots, Miami won't be able to add free agents except through its mid-level exception and veteran's minimum contracts.
Now, let's assume James takes $20 million, but Wade and Bosh each agree to take a $5 million discount. That frees up an additional $10 million in cap space for the Heat to play around with, which could allow them to add a legitimate complementary player for more than just a veteran's minimum.
Convincing both Wade and Bosh to take such a massive pay cut won't be an easy sell. But if it's between that and breaking up the Big Three, they have little choice in the matter.
Find Cheap, Complementary Role Players
Since the Big Three came together in 2010, the Heat's ability to surround their stars with inexpensive complementary talent has been unparalleled.
It started with the five-year, roughly $25 million contract for Mike Miller in the summer of 2010, then continued with Shane Battier (three years, $9.4 million) in 2011 and Ray Allen (two years, $6.3 million) in 2012. All three proved critical in the Heat's back-to-back championship runs, as role players are often wont to do.
The presence of James, Wade and Bosh has also convinced numerous players to sign for sub-market minimum contracts over the years. Chris "Birdman" Andersen and Greg Oden both likely could have signed for more than the veteran's minimum during the 2013 offseason, but both prioritized the chance at a ring over more money.
Of course, it's a lot easier to attract cheap talent when they assume they'll have a legitimate shot at a championship each season. In 2014, if James, Wade and Bosh decide to opt out, free agents won't be nearly as likely to favor Miami until the Big Three re-sign.
The Heat must enter next offseason targeting few complementary shooters who can help provide floor spacing for James and Wade. Ben Gordon, Vince Carter or Mo Williams all stand out as potential 2014 free-agent bench guards that could be ripe for the taking.
Moreover, Miami should share its plans with James, Wade and Bosh before they officially reach free agency. It's a risky move, especially if one or more of the Big Three departs, but the Heat can't afford to be risk averse during this crucial period.
Keep on Winning
Before the Heat even begin to grapple with the business side of this potential free-agent decision, they must focus on basketball.
And what's the easiest way to keep the Big Three together? Keep on winning.
If the Heat take home their third straight championship in 2014, it'll virtually eliminate any chance of James, Wade or Bosh exercising their early-termination options. Who in their right mind would sacrifice a chance at a four-peat, especially considering each has a player option for the 2015-16 season?
The biggest key to another championship run will be avoiding the injury bug. Wade appeared to be a shell of himself at times throughout the 2013 playoffs due to his balky knees, something which the Heat can't afford this coming year.
If Wade's knees break down again and it leads to an early playoff demise for the Heat, LeBron would have to consider taking his talents elsewhere in the 2014 offseason. For him to have any shot of one day usurping Michael Jordan as the greatest player in NBA history, he needs to keep accruing rings on a near-annual basis.
The Cleveland Cavaliers and Chicago Bulls loom as potential suitors for James should the Heat falter during the 2014 playoffs. If Miami three-peats, though, it's unfathomable to imagine any of the Big Three bypassing a chance at a fourth straight title.
Pray Other Contenders Don't Get Stronger
The Heat would like to have full control over their Big Three's free-agency decision in 2014, but barring a third straight title, they won't.
At this point, James, Wade and Bosh have earned the right to flirt with other suitors. That's what back-to-back championships and three straight NBA Finals appearances get you.
By the time the 2014 offseason rolls around, all three players will either be in their prime or already past it. Realistically, opting out may be Bosh and Wade's last chance to secure a major long-term contract.
If other teams with an abundance of 2014 cap space significantly improve by then, it could prove detrimental to the Heat's chances of re-signing the Big Three.
Assuming Paul George gets a max-contract extension by Oct. 31, the Indiana Pacers should be capped out and unable to pursue one of Miami's Big Three. The Cavaliers and Bulls, however, could have significant cap space next summer, depending on some of their other roster moves.
It's not only Eastern Conference teams that the Heat have to sweat, either. The Los Angeles Lakers are currently positioned to have an abundance of cap space in 2014, although one can only assume Kobe Bryant will gobble up a healthy chunk of it.
Once James, Wade and/or Bosh exercise their early-termination options, other teams will smell the blood in Miami's water and pounce accordingly. At that point, the Heat will simply need to pray that they're one step ahead of their competition.
The Likely Outcome?
It's important to keep both the basketball and business sides in mind when considering whether Miami's Big Three will stick around past 2014.
Basketball-wise, if the Heat three-peat, there's virtually no chance that James, Wade or Bosh opt out and bypass a shot at four straight rings. They can always decline their player options following the 2014-15 season and simply delay free agency for a year.
If the Heat fall apart in the playoffs, though, and injuries are to blame, it's entirely possible that at least one member of the James-Wade-Bosh trio will defect.
The Miami Herald asked Wade during the 2013 offseason whether he believed the Big Three would stick together past 2013-14, and he expressed nothing but confidence.
I have no reason to believe anything else. We all love it here. We're all committed to compete for many, many years to come. Obviously, the business side will take over at one point.
Will that love of Miami be enough to convince the Big Three to take another pay cut? Especially if their quest for a third straight title falls apart earlier than expected?
Expect those questions to hang over the heads of the Heatles like an anvil throughout this upcoming season.