Every off-season the Bulls don't win a championship with Derrick Rose they are faced with similar question. Should we go all-in to win the championship next season?
This can be broken down into two primary sub questions:
Should we change the risk profile of how we bring players into the team? [Lakers bringing in Ron Artest, Bulls bringing in Rodman, Pistons bringing in Rasheed Wallace]
Should we take on large amounts of salary in order to increase our odds of winning by a small amount? [Mavs and Lakers both led the league in payroll when they won the title the last two seasons, Celtics have a massive payroll right now, Spurs just signed Richard Jefferson to a ridiculous deal to give it one last shot etc..]
The Bulls have built a very good team. A team that will challenge for an NBA championship without any changes, but also a team that is just as likely to come up empty without one last risk taken to put it over the top.
The risk of bringing on salary isn't a risk to fans. It's simply a risk to the owners. I don't want to go all-in on a Jerry Reinsdorf is cheap rant, because I can understand why he didn't want to splurge on a team with a second round ceiling [even if I could do without the complete outright lies in the season ticket holder letters saying they're raising prices to pay salaries when they're the highest profit margin team in all of sports and then repeatedly dump guys for expiring contracts faster than you can blink in order to avoid the luxury tax].
Given that Gar has little control over the salary risk, since Reinsdorf will either spend or not spend, let's assume for a moment that ownership is going to continue their consistently cheap view and not bring in lots of salary. A view which may also be mandated by the new CBA, at which point Reinsdorf will be off the hook forever in terms of us bitching about how cheap he is [and don't think he isn't one of the owners pushing for this just for that reason, I'm sure he'd love nothing more than to never again have to choose between trying to win a championship and profits or deal with the fans who are upset that he chooses profits].
That leaves us with when it makes sense to take on some character risk in order to attempt to win the title. Maybe the answer is never, and it's quite possible the Bulls could win a title without doing so. I'm proud that this team, as constructed, really doesn't have any complete knuckleheads.
Carlos Boozer's probably about as bad as it gets on the team, and I don't think he's a bad character guy, he's just not a full effort guy.
Generally, championship caliber teams have been able to cope with one complete knucklehead who has brings a lot to the table. The Bulls still don't have their knucklehead yet. They could fill the talented knucklehead void by bringing in J.R. Smith this off-season.
Say what you will about Smith, but he does many of the things this team really needs, and he has the physical tools at the shooting guard position to fill the void we have.
Create his own shot? Check. He's certainly not shy about it either.
Score the ball? Check. He's been an efficient scorer throughout his career.
Shoot the three? Check. Definitely a good outside shooter.
Play defense? He has all the physical tools and would only need to buy into Thibodeau's system.
Is completely available? Check. The Bulls can likely get him next season via S&T even if the MLE is taken away.
O.J. Mayo is another knucklehead who might be available. His knucklehead status probably isn't as well engrained as J.R. Smith's is with fans, but the signs are all there. Multiple drug problems, complaining about minutes, poor chemistry with teammates, decreased role for a guy who appears very talented, etc..
Much like J.R. Smith, you can check all of the same boxes except availability is a tiny bit of a question mark. He was traded for peanuts at the deadline only to have the deal rescinded though, so unless the Grizzlies long playoff run changed ownership's mind [it shouldn't he had a 12.5 playoff PER] about Mayo he's likely available though likely at a higher cost in terms of trade value making it not as straight forward a decision.
The real question is do the Bulls have to go for it now? Common sense would preach that the Bulls have another eight years of Derrick Rose's prime left to decide. They'll probably lock him into a five year deal after the new CBA is ratified, so they'll have a minimum of five.
However, the construction of the team makes their plight a bit more desperate. Carlos Boozer isn't getting any better, and Luol Deng is certainly at his peak now. They probably won't be able to keep both Joakim and Asik, and they might lose bench depth after next season when they have to decide on Korver, Brewer, and Watson's non guaranteed years.
They have a lot of talent that will stick around, but that talent is probably peaking over the next two seasons. If they don't strike over this period than bringing in new players might just break even with the outgoing and declining ones. This season, adding a legit SG is simply a bonus. Everyone else can come back the same, and everyone else [at least everyone important] can come back.
The alternative is to hope for a Pau Gasol trade in a couple of seasons. Maybe some team will be looking to dump a legit all-star for crappy draft picks and expiring deals in two years, but if the Bulls aren't so lucky, then their best chance at a title in the Derrick Rose era with the current core group is in the next seasons.
Maybe they can rebuild a whole new group around him four or five years from now, and they won't have to deal with a Miami team in their prime at that point either, but Orlando has seen how difficult it is to build up while not getting good draft picks and never having cap space.
In short, despite Derrick Rose's age, the Bulls best chance to win it all is probably over the next two seasons. The time to go all-in is right now.