Note: Get used to these discussions, because the A's and Zito are unlikely to have any meaningful contract talks before the end of the season...
The main reason the A's probably won't keep Barry Zito past 2006 is that Billy Beane has done something pretty difficult--and next to impossible with an annual payroll in the low-to-mid 60s--and that is to build a team that figures to be highly competitive without Barry Zito. While assembling a team with arguably as good a chance at the AL crown as any 2006 team, Beane has also assembled a 2007 rotation that will feature a true ace in Rich Harden, 3rd year veterans in Danny Haren and Joe Blanton, a solid veteran "horse" in Esteban Loaiza, and a 5th starter no worse than Kirk Saarloos, a healthy Dan Meyer, or the next best-kept-secret the A's acquire in the next 12 months.
The fact is, the A's rotation, which might be the league's best in 2006, figures to be among the league's best in 2007 even if the A's let Zito walk. There is a reason devotees of AN are so faithful to the A's General Manager: He's really good at what he does, folks.
Will the A's take a serious shot at keeping Zito beyond 2006? Yes and no, I'd say. It is, indeed, a new era of management, and we're seeing it with the Zito negotiations. Whereas Schott told Beane to tell Tejada, "Look, we can't make you a competitive offer so we're not even going to try," Beane has been empowered to tell Zito, "Look, we'd like you to stay and we want to talk, though we know it's going to be hard for us to make an offer good enough to keep you." I expect the A's to make an off-season offer to Zito of between 11-12 million/year, and for some team to offer him 14-15 million/year (it only takes one).
Ultimately, if I had to guess, I would gauge there to be about an 80% chance that Zito leaves after 2006, and about a 20% chance that he signs an extension. The 20% chance is the chance that either Zito decides it's worth taking 3 million/year less to stay with a winning team, a good organization, and a desirable place to live, or the chance that Rich Harden gets hurt again in 2006 and the A's decide they'd better up the offer and commit to Zito--and not Harden--for the long haul.
But having helped the A's take their best shot at the WS in 2006, Zito will probably be walking away from the A's--and the A's will probably keep on winning throughout the decade. I believe it to be a win-win scenario for the A's: they will either keep a fine pitcher for less than market value, or they will avoid committing too much of their payroll to a pitcher who keeps almost being really good.
The way I see it, the only one who stands to lose is Zito--if he chooses to walk away. Jason Giambi, Miguel Tejada, and Keith Foulke all expressed regret or dissatisfaction soon after they left Oakland. Have any players ever regretted choosing to stay?