Should Theo Epstein Break the Red Sox’ Bank Account at Winter Meetings?

Should Theo Epstein Break the Red Sox' Bank Account at Winter Meetings? There's a big check mark on the Red Sox' offseason to-do list next to the word "shortstop," but where does this list go next? The winter meetings may very well solve this mystery since the Red Sox still have holes to fill, a city to please and a rival to dethrone.

Starting Monday, all eyes will be on the Boston brass during the winter meetings in Indianapolis. The club was embarrassed out of the postseason, and to add insult to injury, the Yankees captured their 27th title. Something needs to be done.

And the club has started off on the right foot so far.

With the addition of Marco Scutaro, the shortstop position — a revolving door in Boston since 2005 – should be stabilized until 2012. Now Theo Epstein and company can address the rest of the problems that have stirred Red Sox Nation since Boston's ALDS loss.

Left field is the obvious vacancy that needs a tenant in 2010. The usual suspects — Jason Bay and Matt Holliday — are ready for the taking, but which one will look better in the shadows of the Monster next spring? Do the Red Sox take a gamble on the slightly younger and perhaps more well-rounded Holliday, knowing very well that Scott Boras stands between him and a spot in the Boston lineup? Or does Boston stick to what they know in Bay, who might be comfortable returning to Boston but is seeking top dollar in a market full of eager buyers?

The way things ended in Boston this fall, many experts expect Epstein to do some significant damage to the Red Sox' bank account this winter. Whether it's grabbing one of these big-name left fielders or adding a first baseman via trade, all signs point to a major upgrade to last year's lineup. Especially after seeing their rivals, the Yankees, end up with a World Series trophy after going on a spending spree last winter.

"I think it could go a number of different directions," Epstein told MLB.com earlier this offseason. "I think we're always open to change, because I think you need change to improve as part of the natural cycle in baseball and in life. Sometimes, the market doesn't bear that out. Sometimes, there aren't the right fits. Sometimes, it's not the right free-agent market, and sometimes, you end up with more status quo than you want."

Just because the Red Sox want Bay or Holliday doesn't mean the Red Sox will get them. Almost every team wants these two, and many have the funds to land them. If Boston misses out on both of these sluggers, look for Epstein to take a shot in the veteran free-agency barrel. Players like Jermaine Dye, Rick Ankiel and Marlon Byrd could thrive in the Red Sox lineup at a medium cost. Although this method didn't work for Epstein last season, who's to say they won't land a veteran gem this offseason?

Additions aren't just limited to the offensive lineup. Sure, the Red Sox rotation is all penciled in from Jon Lester at No. 1 to Tim Wakefield at No. 5, but there's always a chance to improve. Roy Halladay is everyone's No. 1 target, but don't be surprised if Boston takes a shot at Ben Sheets, Rich Harden or Kelvim Escobar. All of those pitchers are risks due to recent arm troubles, but there's a very high reward should they remain healthy.

And then there's first base, where everyone from Southie to Newton is crying for Adrian Gonzalez. Boston has trade bait, but it's a little more limited these days than in years past. All of the Red Sox' big prospects (Casey Kelly, Ryan Westmoreland, Ryan Kalish, Josh Reddick, Lars Anderson and Jose Iglesias) are still a year or two away from everyday jobs. Of course, Gonzalez or Miguael Cabrera would look superb in Boston's cleanup spot, but would San Diego and Detroit be willing to part ways with their sluggers in exchange for, say, an impressive young player and a few untested prospects?

We'll find out next week.

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