Baseball's annual winter meetings have begun and this year, the Boston Red Sox have to feel comfortable heading to Orlando considering they have few major league holes, a deep farm system and oh, by the way, they're the defending World Series champions. However, here's a few moves the Sox could make to spice up the winter.TRADE FOR MATT KEMP:
He's available and the Red Sox have a need in centerfield after Jacoby Ellsbury took the payday and ended up in pinstripes. Kemp is an intriguing mix of power and speed but he's saddled with a contract worth $128 million over the next 6 years. He's also sat out nearly a season's worth of games over the last 2 years with various injuries. The Los Angeles Dodgers, Kemp's current team, are willing to eat a portion of his contract for the right players in return. So what would that mean for the Red Sox? A trade that includes Will Middlebrooks sounds like a must. Not only that, the Dodgers are looking for bullpen help, so perhaps a value reliever like Alex Wilson fills a need. From there, the Sox own a dozen high ceiling, low minor league arms that could be thrown in. Would that be enough to get a guy who should have won the National League MVP two seasons ago? What do you think?



Headley isn't as available as Kemp but he isn't likely to be as expensive either. Headley brings a different type of frustration to the table for fans and evaluators alike. On one hand, Headley is a pure athlete with tremendous instincts at third base, a promising bat with solid power and he's patient at the plate. Unfortunately for Headley and the San Diego Padres fanbase, injuries have been the major factor in Headley being unable to live up to all of his promise. He's in a contract year, and while the Padres would like to keep him, if they're given a sweet offer, it might be hard to pass up. Most teams are looking for inexpensive pitching help, and the Sox have plenty of that to offer. But the Padres will want a premium prospect, likely an infielder, in order to pull the trigger on a trade of the guy that serves as their current franchise player. Perhaps a deal thats built around pitcher Allen Webster and infielder Mookie Betts would get the job done. Too rich for my tastes. What do you think?



Choo is the last big positional free agent on the market for 2014. Last season, he spent the entire year playing centerfield for the Cincinnati Reds. Choo is probably better served playing a corner outfield spot and thus, he should at least be on the Red Sox's radar. Choo is an on base machine, who also boasts a consistent average and moderate power. All of this makes him very attractive to any major league team. But there's a catch (or two). Choo is already 31 and will turn 32 in the middle of the 2014 season. Choo is also represented by Scott Boras, who is well known for getting contracts of insane worth for his clients that generally never live up to them. A safe bet on Choo would be that he's looking for a 5 year deal at $20 million annually. It's not outlandish by today's baseball standards but still something I'd prefer to the Red Sox avoid. What do you think?