Last season, the Chicago Bulls had one of the best benches in the NBA, which was a huge reason they were so successful despite all those Derrick Rose injuries. But when bench players begin playing like starters, it’s safe to assume they’ll eventually get paid like one. While the Bulls would love to pay every talented player on the roster what he deserves, the salary cap doesn’t always allow for that.

That’s why the Houston Rockets’ three-year, $24.3 million dollar offer sheet that center Omer Asik has verbally agreed to will be so hard for the Bulls to match. General manager Gar Forman has said all along that he would match any offer for Asik, that his decisions would be based on basketball, not finances, but that might change thanks to the odd nature of this contract, constructed as a third-year “poison pill” deal thanks to the Gilbert Arenas provision in the new CBA.

In the first year of the deal, Asik would make $5 million, followed by about $5.2 million in year two. That third year would pay the center over $14 million, however, which is what could force the team to balk. The loophole here is that the team offering the deal is allowed to average the cost over the life of the contract—$8 million a season in this case—but the team matching the deal has to count actual numbers against their cap. Chicago would be fine in years one and two, but year three would destroy them as repeat luxury tax offenders, which they could very well be by 2015.

If they were to match the offer sheet to keep Asik, Chicago would have $59 million already committed to four players (Asik, Rose, Joakim Noah, and Carlos Boozer) for the 2014-15 season, though there’s virtually zero chance the Bulls keep their fingers off the amnesty trigger with Boozer by that point. Even if they remove his salary off the books that year, they’ll still be on the hook for $45 million for the other three, which is quite a bit of money committed for a team three years away.

Regardless of what happens down the line, though, a match for Asik would bump them right up against the luxury tax threshold for next season, despite the fact that they’d only have nine players under contract. Assuming they cut Kyle Korver, who only has $500,000 of his next year’s salary guaranteed, the Bulls would be less than $1 million away from paying luxury tax, and this isn’t a team that typically bites the bullet and pays the luxury tax. Considering Rose is out for most (if not all) of next season and the new CBA is so punitive for repeat tax offenders, it would be hard to justify paying it next year, when expectations are relatively low for the team anyway.

To match Asik, Chicago would have to amnesty Boozer at some point (which they were probably going to do anyway), and then eventually make a decision between Noah and Asik sometime before the ’14-’15 season begins. There’s also the possibility that, by the time Asik is in that pricey third season of his deal, a $14 million expiring deal for a talented young player could end up being a pretty nice trade chip.

And none of this even takes into consideration retention of Luol Deng or, perhaps more interestingly, an eventual extension for Taj Gibson, which would be almost impossible to do with this kind of money on the books. Gibson might be the more valued asset for the Bulls, particularly if Boozer isn’t in the long-term plans for the team. There’s also the argument that using the amnesty provision on Boozer shouldn’t be to re-sign the bench, but to bring in another star. Do great teams hamper themselves with expensive benches, or invest in studs and then rotate the role guys in and out as necessary?

Whatever ends up happening, Houston did their job in offering Asik just enough money to be reasonable (an $8 million-per-year average isn’t outrageous for him at all), but also just enough money to make the debate about matching plenty interesting. Two weeks from now, we’ll see what the Bulls do, but Forman and team president John Paxson are almost surely cursing Daryl Morey as they begin their deliberations. Between the money they’d have to pay to amnesty Boozer to keep Asik, or even the luxury tax penalties they’d have to pay for Asik, it results in Chicago paying way more than they need to for a backup center. That’s why it doesn’t seem likely the Bulls will match this deal.

Houston definitely has put Chicago in quite a pickle, which perfectly personifies the delicate art of signing restricted agents under the new CBA. And it won’t be the last time we see the Gilbert Arenas loophole used in free agency, either. This one’s just the first.