It's close. A lot depends on how he fits into your overall plan. If you can bump payroll to $115-120m next year and believe that you can add another bat on top of Headley, replace Garza and fix the bullpen, then you can probably justify it. If you can't afford to do all that, then I think you'd be better served waiting to see what the (admittedly thin) free agent market can bring and commit your money there rather than trade prospects for the privilege of giving Headley an FA-cost extension. If 3b was our only hole, then it'd be more pressing. But we can make plenty of strides next season in the OF, the bullpen, 2b, catcher, replacing Garza in the rotation.