The trading deadline is an important decision point for many teams. In any given year, there are teams that, while playing in medium or even small markets, are still in strong contention in late July and not have a chance not only at making the post-season, but of playing deep into October. This year these types of teams include the Rays and Rangers in the AL and the Reds, Giants and Padres in the NL. The remaining contending teams are primarily big market teams like the Yankees and Braves.

Teams like the Rangers and Giants need to determine whether or not this could be their year in the weeks preceding the trading deadline and act accordingly. The Rangers seem to have already decided that 2010 could be a special year for them as they have already traded several top prospects for half a season of Cliff Lee. It is not yet clear what other teams like the Reds or Giants will do.

There is another group of teams for whom the trading deadline raises a different set of questions. These are the big market teams like the Yankees and Red Sox, and to a lesser extent Angels, Dodgers and Phillies. These teams have all created a narrative, although none more than the Yankees, that they need to win every year. This narrative means that they go into every trading deadline as a buyer, never as a seller. Over time, this can lead a team either to empty out their farm system in search of that elusive final missing piece to a championship or to miss opportunities by trading proven players for prospects. This was the treadmill on which the Yankees found themselves between 2002-2008.

While it is easy for a team like the Mariners or Astros to realize that Cliff Lee and Roy Oswalt are not going to help them win a championship anytime soon and to cash them in for prospects, big market teams are almost constitutionally unable to think that way, thus losing the opportunity to retool for the following season or two. As these players age they become expensive liabilities for these big market teams. Given the inequality in baseball, it does not seem to be some cosmic injustice that a team like the Yankees, Red Sox or Phillies will get saddled with the occasional big unmovable contract or two, but the phenomenon is still real.

In 2010, the team for which this dilemma is most acute is the Red Sox. In recent years, the Red Sox have emerged as one of the biggest spending teams outside of the Bronx. They have also, and equally significantly, sought to become the smartest run team around. Theo Epstein is, other than Billy Beane, the most prominent of the new generation of smart, sabrmetric savvy group of GMs. Epstein has added to the Red Sox brainpower by bringing in Bill James himself as an advisor.

The Red Sox have had a rough 2010 due to injuries, slumps and age. The team got off to a rough start, but played very well from mid-May through the All-Star break. Currently, with about 60 games remaining the Red Sox are seven games out of first place and five games behind the Rays for the wild card. It will not be easy, but they could catch the Rays and maybe even the Yankees. This would suggest that the Red Sox should be buyers at the deadline. However, another approach might be to recognize that while the Red Sox might be able to sneak into the playoffs as the wild card, this is not the type of team that, even if it snuck into the wild card, can play far into the playoffs and to be a seller.

For small and medium market teams this approach is difficult because these teams need the occasional playoff berth to keep fan interest. For teams like the Red Sox, however, a playoff berth will not be enough. If the goal is to win it all every few years, acknowledging that this goal cannot be reached every year is an enormous strategic breakthrough. The Red Sox would be in a much better position in 2011 if they could be sellers now and move older players like J.D. Drew, Mark Cameron or even David Ortiz for players who could help next year and beyond.

The baseball rationale for doing this is not entirely obvious, but a good argument can be made for it. However, trading players of this caliber would be a difficult sell in the media and throughout Red Sox nation. In this respect teams like the Yankees and Red Sox have made themselves prisoners of the expectations they have created.

Lincoln Mitchell