Possible SP Acquisitions
Roy Halladay (trade)
Felix Hernandez (trade)
Rich Harden (FA)
Ben Sheets (FA)
Justin Duchscherer (FA)

Tim Wakefield has a $4-million club option for 2010, with a perpetual annual club option until Boston declines to exercise the option once. Theo Epstein has indicated that Wakefield is in the team's plans for 2010.

Possible RP Acquisitions
Billy Wagner (FA)
Ron Mahay (FA)
Scott Eyre (FA)
Kiko Calero (FA)
Russ Springer (FA)

According to WEEI.com, Boston declined Takashi Saito's $6-million club option for 2010, ultimately resulting in Saito declaring himself a free agent.  Regardless, it is believed that the two sides may still negotiate a deal for 2010.

Fernando Cabrera pitched quite well for the PawSox in 2009, but struggled in limited major league action.  He has 3+ years of service time, making him arbitration eligible this off-season.  He could be one of the first cuts if the Sox need space on the 40-man this winter, but if he makes it until January, he's a candidate for a non-guaranteed pre-arbitration deal.  He's also out of options, meaning he'd have to clear waivers in order to go back to Pawtucket.

Miguel Gonzalez was selected in the 2008 Rule 5 Draft from the LA Angels.  He spent the entire 2009 season on the DL after March 2009 Tommy John Surgery.  As such, the Sox will need to keep him on the active roster for an aggregate of ninety days in 2010 or they must return him to the Angels.  He'll likely remain in the Sox organization until he returns to the mound, at which point he may see some rehab time in the minors. However, he'll make a major league salary for whatever time he rehabs next season, so don't expect the Sox to give him a long rope.  

Victor Martinez has a $7.5-million club option for 2010 that the Sox are expected to exercise.

Possible 1B/3B Acquisitions
Prince Fielder (1B) (trade)
Adrian Gonzalez (1B) (trade)
Chone Figgins (3B) (FA)
Adrian Beltre (3B) (FA)
Carlos Delgado (1B) (FA)

Alex Gonzalez has a $6-million mutual option for 2010.  It is believed that Gonzalez will return to Boston next season, but there is some speculation that the two sides may attempt to restructure a new deal first.  If the Sox don't bring Gonzalez back, a long-term Type A free agent signing is unlikely.  In that case, JJ Hardy, Adam Everett, and Jack Wilson could be potential targets. Hanley Ramirez is also an outside possibility as a trade target, but would come at a hefty price.

Jason Bay is eligible to become a free agent fifteen days after the end of the World Series. He will likely test free agency, but he has indicated that Boston is one of the few teams on his radar.  If Boston is unable to sign Bay, other free agent outfielders that the Sox might target include Matt Holliday, Bobby Abreu, and Gary Sheffield.

Possible C Acquisitions
Jason Varitek (mutual option)
Henry Blanco (FA)
Ramon Castro (FA)
Brad Ausmus (FA)
Miguel Olivo (FA w/ option)
Ramon Hernandez (FA w/ option)

Possible OF Acquisitions
Rocco Baldelli (FA)
Jerry Hairston Jr. (FA)
Reed Johnson (FA)
Cody Ross (trade)
Ryan Spilborghs (trade)

George Kottaras has just 1 year and 21 days of major league service time, meaning Boston has the option of bringing him back as the backup catcher for the major league minimum in 2010.  However, he is out of options and thus can't be assigned to the minors without clearing waivers.  Given that Kottaras threw out only 16.1% of would-be base stealers in 2009, the Sox may look for a more defensive-minded backstop for the 2010 season.

Casey Kotchman will be arbitration-eligible this off-season, meaning he will likely receive a raise from his $2.89-million salary from 2009. The problem for Kotchman is that there doesn't appear to be a lot of space for him on the 2010 roster unless the Sox anoint him the starter at first base.  Even if Boston doesn't sign a corner infield bat this off-season, there will still be a crunch for playing time at first and third base next year between Kevin Youkilis, Victor Martinez, Mike Lowell, and even David Ortiz when the Sox play in NL parks. As Kotchman is good enough to start for a mid-market team, and his contract is still relatively reasonable, he may be a candidate to be traded this off-season.  Otherwise, he'll be an excellent bench option for the 2010 club.

After getting off to a nice start in 2009, Nick Green hit just .167 in the second half and missed a lot of time with a bulging disc in his back. He's arbitration eligible this off-season with just over four years of major league service time.  The 31-year-old may be a candidate to sign a non-guaranteed major league deal outside of arbitration in the hopes of making the club out of spring training.  However, if the Sox need space on their 40-man roster this winter, Green may be one of the first names on the chopping block. He'll likely need to prove that he's healthy if he wants to nail down a major league deal with any team.

Joey Gathright is arbitration eligible this off-season as he has 3+ years of major league service time.  Gathright could be back in 2010 if the Sox fill the other bench spots with some bats, but he's really better suited as a fifth outfielder.  Unfortunately he doesn't really complement JD Drew enough to serve as Boston's first outfielder off the bench. Brian Anderson remains an option off the bench, but he has one option left so the Sox may stick him in Pawtucket to start 2010.  Similarly, Josh Reddick is probably better served paying everyday in Pawtucket to start the 2010 campaign.