The Red Sox are walking away from 2009 season realizing they are going to need more.  They watched the 2009 Yankees be the first team in the Wild Card Era to use a three pitcher rotation to win a World Series.  Meanwhile the Red Sox lineup completely stalled and as they were swept in the first round by the Angels.  The Yankees used a stellar line up to power their way through the playoffs (as well August and September) with only three major league starters.  Now the Red Sox realize that they have to improve in order to compete. 

The biggest weakness this postseason was their offense.  Before they are going to improve they are going to have replace their second most productive hitter from last year Jason Bay who has become a free agent.  Bay's .267/.384/.537 is not easily replaced as he had the highest on base plus slugging of any regular AL OF.  The Red Sox were able to get Jeremy Hermida however the former stud prospect is not at Bay's level offensively yet and may never get there.  That leaves only a few options to improve offensively.

One step is signing Bay again.  The big problem with this is Bay is a poor defender.  And as he gets older his defense will probably suffer even more.  Bay will most likely end up DHing in a couple of years. And Bay is looking for a large contract which he should be entitled due to his work at the plate.

The only other LF bat on the market is Matt Holliday.  Holliday's career numbers .315/.385/.545 which were certainly replace Jason Bay's bat.  Holliday is also a considered a plus defender.  Holliday has a more complete game and is a younger than Bay.

However Holliday will be costly.  Not only would he cost a draft pick, but you have deal with his silver tongued agent Scott Boras, the man who could get Hugh Hefner take one for the team and talk up a fat girl at the bar.  It is going to take a small fortune to sign Holliday though Holliday certainly has the skill to warrant a paycheck.

While on paper Holliday seems like the ideal candidate for LF in the free agent market, there have been questions about his make up.  Several columnists have quoted GMs and scouts wondering if Holliday has the make up for a big media market.  Holliday himself has made several comments alluding to his preference to stay out of the limelight,

Players in Boston cannot shy away from the media especially players getting the kind of contracts Holliday will be receiving.  He will have a huge target on his back and will expected to perform at an all star level from the get go.  Anythign less it will start to get ugly in Boston.  If Holliday is the kind of players tha lets that rattle him we will be in for long suffering both the fans and Holliday.

The last RHH LF we signed to major contract forced his way out of town.  He hated playing in the Boston media spotlight.  Despite his misgivings, Manny still smashed the ball.   Then again Manny would probably hit if people were rioting outside his house every night.  Manny was able to overcome that stuff as soon as got in the batter's box.  Some playersdon't have that ability though.  Renteria struggle his entire time in Boston just to be shipped to Atlanta where he had an all star season.

That is why it may be better to sign Bay who is already accustomed to Boston and has succeeded here.  Holliday may not be able to adjust a town who will crucify you even if you are producing.  People crucify JD Drew still despite him being the second best hitting OF in the AL this year.  There is just too much money at stake to risk on player thats not ready to play here.