The bidding for Lee is pretty much a two horse race at this point. Boston essentially took themselves out of the running for him last year when they signed Lackey, then extended Beckett.
Right now, the most pressing issue for Boston this post-season is surrounding Adrian Beltre.
Needless to say, Beltre lived up to his one year contract, finishing in the top five in the American League in WAR (both offensive and defensive), Batting Average, Slugging Percentage, On Base Percentage, Hits, Total Bases, Doubles, RBI, OPS, Runs Created, Extra Base Hits, Putouts, Assists and fewest errors committed.
Traditionally, Beltre has been a Gold Glove caliber 3B, and it could be argued on defense alone, he's one of the best in the sport. While he takes a fair amount of criticism for his offensive production in Seattle, minus his final season there, he averaged over 20 homers and 80+ RBI (26 in three of five) in a pitcher friendly ballpark.
His numbers in his first (and possibly only) season in Boston did spike (his batting average was over 50 points higher than his norm, and he was 3-4 homers up from his norm), however it is concievable that these could have been him benefitting from a much more hitter friendly ballpark, and being in a lineup with more protection than he had in Seattle and Los Angeles.
Question is, do you give Beltre the reported 4-5 year deal worth $14 million per that he's looking for?
Also, another decision seems to be looming with Victor Martinez. Reportedly he too is looking for a 4-5 year deal with $12 mill as a starting point. Do you give that kind of loot to a catcher who is going to be 32 at the start of the 2011 season, and the essential reality that he's slowly moving into DH territory?
Chances are, even with Boston's payroll as is, there's a zero percent chance they could and will keep both, leading towards the "which do you pick" debate. Of course, there's also the rumors that the Sox could be linked to Adrian Gonzalez and Prince Fielder, both of whom are expected to be shopped extensively this off-season.
You're Theo Epstein. Which avenue do you go with this? Do you re-sign Martinez, do you re-sign Beltre or do you make a run at one of the bashers (Gonzalez/ Fielder) and shift Youkilis to 3B full-time?