The Key to Landing Holliday: Jason Bay?

Scott Boras is hoping that negotiations between Boston and Jason Bay fall apart.

Scott Boras is hoping that negotiations between Boston and Jason Bay fall apart.


                With baseball’s winter meetings in Indianapolis just 9 days away, the hot stove figures to pick up steam quickly. Although there aren’t a lot of signings or trades happening yet, agents and general managers are very busy laying the groundwork for possible deals in the future. John Mozeliak figures to have a busy time in Indianapolis, as he will have to continue to go forth with his parallel tracks off-season plan (click here for an explanation). Matt Holliday is obviously plan A and the goal of the off-season, but the key to landing him might be what happens with Jason Bay and the Red Sox.

                After missing out on Mark Texeira last off-season, the Red Sox definitely need to add a big bat this winter. Jason Bay has performed very well for Boston, but recently rejected a 4 year $60 million dollar offer. Bay can hit, but his defense leaves something to be desired, and one of General Manager Theo Epstein’s goals this off-season is to improve the Red Sox defense. Theo said this in an article, stating: “If you look back at this year’s club, I think we weren’t the defensive club that we wanted to be. So there’s room for improvement with our overall team defense, our defensive efficiency.” Holliday would be an upgrade over Bay defensively, and with left-field and shortstop the only two positions that the Sox need to fill through trades or free-agency this winter, Matt Holliday could be a great fit in Boston.

                Why is Boston such a key in the Holliday negotiations? Matt Holliday is a Scott Boras client, which traditionally means that the client will sign with the highest bidder. In this Wednesday’s post I explained why the Cardinals had to look for value in their free agents because of their $100 million dollar payroll, but in Boston’s case Theo Epstein can afford to pay market value for players because of higher payroll Boston has. Boston’s payroll has been in the $121 to $143 million range the last 3 years, so the Sox top offer could top the Cardinals top offer because of the payroll disparities between the two teams.

                Another variable in the Holliday negotiations if Bostons gets involved are the Yankees. I dubbed them the “sleeping dog” in the process in my post that focused on potential suitors for Holliday, because although the Yankees appear willing to bring back Johnny Damon now, if Boston goes after Holliday the Yankees will likely enter the bidding as well. Even if the Yankees have no intention of signing Holliday, they will likely bid just to drive up the price on Boston, which would probably make the Cardinal’s offer a distant third.

                Of course this could all just be speculation of Bay re-signs with the Red Sox, which is a possibility. Theo also talked about a potential deal with Bay in that same NESN article, stating that “he hopes it does (happen).” Bay will likely be cheaper than Holliday, and with the Red Sox in the Roy Halladay trade talks, Josh Beckett needing a contract extension, and the fact that they still don’t have a shortstop, it’s possible that Bay could be a more attractive option than Holliday because of the price. This year’s winter meetings figure to be an exciting time for Cardinals, and in addition to paying attention to the Holliday negotiations, need to follow the Bay situation as well.





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