This is stupid. Sign an extension now when his value is not great. Sure, in the worst case scenario, you may dodge a bullet if he tanks this year, but barring an unmitigated disaster, there is little to gain. The scenarios as I see them are: 1. If he has a great year, you end up paying more. Lots more. 2. If he has a so-so year, you still have to bring him back (there are no other real options, within the organization, or via free agency) but then you pay more because other teams are in the mix. 3. If he has a bad year, you may be able to save some money, but you have to bank on the fact that no team will pony up the cash and gamble that he returns to form. In other words, you might save money, but you might not. 4. If he has a bad year, and suffers some sort of injury that will affect the rest of his career, you've dodged a bullet. To me, scenarios 3 and 4 are not enough to offset 1 and 2, which I feel, are more likely to happen anyway. Plus he's a home-grown player. Sandy should be talking to him right now.