With Mike Napoli re-signing with the Red Sox for 2-years $32 million - the biggest off-season priority for Boston is done. So what is left for Ben Cherington to do at the Winter Meetings? Here's my Top 5:
1. Find a super utility guy - someone who can back-up 3rd, SS and 2nd. Seriously - the pitching staff and the position players are pretty set. As other teams try to fill gaping holes - the Red Sox biggest need is a capable utility guy. Stephen Drew could fit the bill with at-bats shared between Drew, Xander Bogaerts and Will Middlebrooks and there are many who want Drew back but I'd prefer to have Bogaerts play short fulltime and the Red Sox to enjoy the supplemental pick they would get when Drew signs elsewhere.
2. Sign Jon Lester to an extension. He recently said he wants to stay in Boston and would be open to a home-town discount contract like the one Dustin Pedroia signed. Take him up on it before the costs of top shelf starters goes crazy. Say 5-years $100 million? Everyone happy?
3. Trade Ryan Dempster and his $13 million contract. Boston has six starters and only 5 slots. Trading Dempster and his $13 million contract makes the most sense. Of course you could always wait till Spring Training to do this in case of injury.
4. Trade Ryan Lavarnway to a team that needs a catcher. I like Lavarnway but there just isn't roster room either in the bigs in Boston or AAA in Pawtucket. Once again - maybe wait till Spring Training.
5. Sign David Ortiz to an extension. I know both sides agreed to no extension until the current contract was done but that was before Ortiz was World Series MVP. How about 2-years and $30 million?