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Jason Bay has been waiting a long time for his big payday, and after an excellent 2009 season, he’s all set to cash in. I don’t blame the guy – how many chances does a guy have in his life to sign a contract worth $50-60M or more? Sports Illustrated has reported that Jason Bay has turned down a Red Sox offer of 4 years and “close to” $60M, and gone to free agency. Keep in mind that this report is from Jon Heyman, who Scott Boras routinely uses to achieve his ends; in this case, it seems he wants to drive up the market expectation for left fielders and his client Matt Holliday in particular. In Hot Stove double-talk, “close to” could mean anything, so I wouldn’t read too much into this. I, for one, certainly hope that the Red Sox will NOT go past this offer to Bay. Here’s why.

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Matt Holliday will likely get the biggest deal this offseason, but he’s no Mark Teixeira.

John Lackey might not be as good a signing as some think, warns FanGraphs.

FanGraphs gives an argument as to why trading for David DeJesus might be a better move than overpaying for a top free agent left fielder this offseason. Xavier Nady could be average with the bat, but don’t expect his arm to be what it used to be.

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The Red Sox definitely need a contingency plan in case they can’t land Matt Holliday or Jason Bay this offseason. Theo Epstein and company have been thinking outside of the box, even looking at acquiring Dan Uggla to play in left. A right-handed OF with some power who could play left field in Fenway. Hmm, let’s see. How about asking Vladimir Guerrero to move to left?

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As expected, catcher Jason Varitek has chosen to exercise his $3M player option to stay with the Red Sox in 2010. My guess is that the front office will keep him on as the backup catcher until he starts hitting (er, whatever that was) like he did in the second half of 2009. The Sox have already announced that they plan to make Victor Martinez the “full-time” catcher next year, which basically means he’ll be catching a lot more than 50% of games, as he has done for the last few years. Let’s hope his body and hitting hold up under the extra workload.

All the comparisons have been between Jason Bay and Matt Holliday, but Dave Cameron touts Mike Cameron (no relation) as a better free agent signing. Preview: it is about the defense, but even if you discount the UZR numbers 50%, it still works out in Cameron’s favor. Bay is likely to sign for as much as 5/85, while Cameron may get 1/10. R.J. Anderson confirms what I said about the rumor that the Sox had an offer of 4/60 on the table for Bay, that it’s probably just a Scott Boras lie.

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I know, he’s an injury risk and a punk, but outfielder Milton Bradley is reportedly eminently available. After signing him to a 3-year deal just last offseason, the Cubbies can’t wait to deal him. As we know, the Red Sox front office is all about “value” these days (for better or for worse). In baseball, one man’s garbage could be another man’s treasure; and this garbage could come cheap, given the circumstances.

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Hmm, I didn’t see this one coming. Not at all. The Red Sox today traded LHPs Hunter Jones and Jose Alvarez for the rights to 25-year old OF Jeremy Hermida, who is entering his second year of salary arbitration. The 6-2, 222 Hermida has been slightly above average playing for the Marlins in the NL. As far as we can tell, he is potentially the fourth outfielder for this club in 2010; he may also be a trade chip as part of another deal. I think the latter may make more sense, because Hermida is pretty wretched with the leather and the Sox have more need for a right-handed OF reserve to spell J.D. Drew. So let’s take a look at what we got:

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Look, I love Jason Bay as a human being. And I appreciate all that he’s done for the Red Sox since arriving in Boston a season and a half ago. But he’s just not the guy for the Red Sox to sign this offseason – he’s coming off a career year and a half, and he plays defense roughly like a bump on a log. To think that he may sign a deal on par with or even bigger than Matt Holliday this offseason just boggles my mind.

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You’re going about this all wrong. Would it be nice to get an elite slugger or a young ace this offseason? Of course! But at what price? Despite how it looked at times, the lineup is strong, and finished 3rd in runs scored, despite playing Nick Green and Jason Varitek as much as we did. And the rotation already has four strong pitchers if Daisuke Matsuzaka can come back. Trading Clay Buchholz now is the wrong move; he will give you 80-90% of what Hernandez will over the next four years at a bargain price. The Red Sox have talent and should continue to build from within. We certainly need to address that left field vacancy, as well as the lack of pop in the lineup; signing Matt Holliday should be enough on both counts, and we can fill in as needed around these guys. Here’s how to approach the off-season with measured restraint:

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It’s all well and good to consider all of the free agents and trade possibilities out there, but in my mind, you have to set a direction by placing the most important piece of the puzzle first. Then you fill out the roster based on what you have to do to get that piece. Here’s a look at some of the major pieces available, and what it might cost to land them.

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We’ve covered our impending free agents here. Now we need to step back and see what the team looks like, sans those guys we’re gonna let walk. Then we can examine our strengths and weaknesses and formulate a plan for the offseason. Let’s take a look at what the Red Sox have already in-house, and what players could be gone:

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Fenway header image by Eric Kilby, used by permission under Creative Commons.

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