Theo Epstein & Red Sox – Free Agent Wish List

This year, unlike any other, GM Theo Epstein and the Red Sox will have to be at the top of their game in order to stay ahead of the curve. With a “weak” free agent market, there are few options for the Red Sox to target. If the Red Sox were to fail in their attempts to sign at least 1 or 2 of those top tier free agents, it will surely be considered a “failed” off-season for Theo & Co.
At the top of the list is Jason Bay. The Red Sox and Bay have been engaged in extensive negotiations to bring back the left field slugger for 4 or 5 years. But Bay has acknowledged that he is going to test the free agent market. If the Red Sox cannot get a deal done, where will Theo & Co. turn?
Epstein and uber-agent Scott Boras held talks regarding Matt Holiday among other things during the GM meetings last week in Chicago. The issue is how far to go with Boras and Holiday when they don’t know if they’ll win out in the Bay sweepstakes.
The Red Sox have also expressed interest in John Lackey as we have previously discussed, but it is unlikely that they will shell out the cash for an “older” pitcher who has dealt with are issues each of the last 2 seasons that have prevented him from pitching 200 innings in each of those seasons.
As we predicted, the Red Sox declined the $6 million club option to re-sign Alex Gonzalez at shortstop. They could try to re-sign him as a free agent at a “reduced rate”. The Red Sox are not sold on Jed Lowrie yet because of his health (Epstein said this about Lowrie: “We’re going to acquire somebody to be our shortstop. At this point, Lowrie has to prove his health… We can’t allow ourselves to have instability at shortstop again if he’s not able to answer the bell health-wise… He has to show up abd do it day in and day out before we rely on him. So yeah, we’ll be acquiring a shortstop via trade or free agency.”). Free agent shortstops Marco Scutaro and Orlando Cabrera are both Type A free agents, so if the Red Sox were to sign either player, they would have to supply 2 draft picks in the 2010 First-Year Draft, something Theo & Co. might be opposed to doing.
Theo & Co. always explore trade opportunities as well. Could that mean a move for 1st baseman Adrian Gonzalez or starting pitcher Roy Halladay at some point this off-season? Maybe, maybe not, but we will likely hear the Red Sox in the mix for either or both players as the season progresses…
For some reason, I have a bad feeling about this off-season. I really hope they sign Bay, even though I think that Holiday may be the better player. In any event, I am worried that if they fail to sign Bay, they may be late to the Holiday table. Hopefully they made it clear to Boras to keep the Red Sox in the loop as he progresses with any moves for Holiday. But if it does get to that point, Boras will know that the Red Sox are in a jam to sign one of those guys, and they could end up shelling out major bucks to make sure they have a great left fielder patrolling the grass in front of the Green Monster for years to come.

Interesting times for Theo & Co. and Red Sox Nation. Fasten your seatbelts for a bumpy ride – we’ll keep you posted along the way…
