The Bulls have plenty of tough decisions this off-season that depend largely on how much luxury tax they're willing to pay now, how much luxury tax they're willing to pay in the future, and how much they want to go for it this season
Is Omer more valuable than the MLE?
I like Omer, I'd like to keep Omer, but if I can get a TPE and a future 1st from Houston for Omer, then I let him go. The question ultimately comes down to whether Omer is more or less valuable than the MLE and ability to use a S&T. It depends whom the Bulls can get for the MLE of course, but if they can land Brandon Rush, Nick Young, Lou Williams, Courtney Lee, or O.J. Mayo with the MLE then I'd be tempted to go that route over keeping Omer.
Omer is valuable, but he's less valuable to Chicago whom already had a ton of money tied up in the front court. If you're going to lose one of your big men, Carlos Boozer would be the number one choice. However, given that there aren't likely any takers for Boozer, Omer Asik should be next on the list. I'm tying myself to Noah and Gibson as the big men I want to stick around for the future. Particularly with Mirotic being the guy who comes over in a couple seasons.
That said, there's no guarantee you can get one of those players for the MLE either. Lee, Rush, and Young are restricted. Lou Williams will likely sign for more than the MLE to stay with Philly, and O.J. Mayo may get a better offer as well.
How much do you offer Taj in an extension?
I think if Taj has another healthy, productive season, you have to assume he's going to get 9-11 million in offers from other teams. Lowering the number of years in deals has also made teams more aggressive in the total dollars they can offer per year. Four years simply isn't that long of a time even if you box yourself into something crappy. Typically, if you like a guy enough to make him an offer one year, you won't sour on him until at least season three at which point he's a relatively short term problem.
As such, I'd probably start negotiations with Taj at around eight million per season, but I'd come to terms on an agreement at nine million if I had to. If you're not willing to pay Taj nine million next season then you need to start exploring trades for him right now and attempt to get as much value back as you can, because he'll be gone anyway.
Do you keep one of Korver, Brewer, or Watson?
If you want to win, the obvious answer would be yes. Particularly if you keep Omer Asik as well. The luxury tax bill will be higher, but the Bulls will spend a half season [minimum] trying to replace Rose, Watson, Brewer, and Korver with Jimmy Butler, Marquis Teague, and some guy making 3/9.7 [which is less than all four of those guys].
Brewer is better than Butler, Watson will almost assuredly be worlds better than Teague initially, and some dude making three million isn't likely to replace Korver. We still haven't touched on how you make an attempt to replace any of Rose's skills [obviously impossible to replace his impact]. However, if the Bulls keep Watson around, then they can use that MMLE slot on a wing player to help add depth.
This might be crucial if Rip Hamilton is unable to play significant minutes and given his past few seasons why would we expect anything other than significant Hamilton injury problems? I don't think Rip is a bad dude, and I think he can still help a team while healthy, but he's not someone I want to count on at this stage of the game.
In short, if you can only bring in one non vet minimum guy to go along with one rookie and need to replace three quality veterans and a superstar good luck. If you can at least keep one of those veterans it would help significantly.
The long term tax implications will decide on Asik
This is a tough year to stomach going into the tax if you're going to be squeamish about paying it later. The Bulls aren't likely to compete for a title this season with Derrick Rose coming back mid-season to likely considerably less than 100% form. They will field a similar team to last year except losing three valuable role players for three guys who are worse.
If you keep Omer, you'll almost certainly be in the tax this season, and even if you just dip a toe into it, it sets up the Bulls to become repeat offenders down the line. It will become difficult to avoid the tax the next two years as well. While Chicago won't necessarily be deep in the tax in any of the three years [probably 3-8 million], they'll get hit with a repeat offender bill in that third season.
The alternative would be to make a move like trading Noah, Deng, or letting Taj go in order to avoid the tax, but then if your plan is to keep Omer over one of those guys you'd better simply rethink that plan. Omer's an incredible defensive player, but he's one of the worst offensive players in the NBA.
In short, the contract isn't that difficult to match for Chicago as overall it's at market value with two years being under and one being over. The year that's over the Bulls are largely expected to amnesty Carlos Boozer which would get them back into reasonable tax shape while Luol Deng will have expired and may be playing elsewhere or, at a minimum, take a paycut down to the 10-11 million dollar salary range.
In short, the poison pill in year three really isn't that poisonous to Chicago, but they'll likely considerably hurt the team or be in the low luxury tax area for the next three seasons if they keep him.
Cheap options to chase?
It's hard to know who will be a cheap option out there. In June we're worried about Steve Nash taking a huge discount to play with the Heat and where all the ring chasers will go. In July, we tend to laugh at how silly those thoughts are as basically ever player follows the money [nor do I blame Nash whom would give up 27 million or so to sign with the Heat].
As such, the options available won't really be known for another couple weeks when we see who shakes out and who doesn't. Kirk Hinrich, Delonte West, Brandon Roy, Ramon Sessions, Willie Green, and Derek Fisher are names being kicked around right now, but we'll see how many of those guys are really left when all the better offers are taken.