Jon Lester and Why the Red Sox Are Smarter Than the Yankees

As the baseball trading deadline approaches, one of the most intriguing players who has been connected to trade rumors is Boston Red Sox pitcher Jon Lester. Lester is a top flight starting pitcher who was one of the mainstays of the Red Sox rotation during their 2013 World Series winning season. Lester was even more impressive in the World Series itself where he won two games while giving up only one run in just over fifteen innings. Lester was a strong candidate for the World Series MVP last year, in the other than David Ortiz bracket, of course. Lester is also a free agent after this year and could bring Boston valuable prospects from any team looking for a potential ace in the stretch drive and post-season.

The Red Sox might not be able to trade Lester, or the the prospects they get for Lester may not turn into valuable players in the future, but the willingness of the Red Sox to shop Lester demonstrates why the Red Sox are one of the smartest organizations in baseball. It also presents a stark contrast between the Red Sox and their top rival the New York Yankees. In recent years, the Yankees have never accepted that they are out of contention or decided to trade a player approaching free agency. This has contributed to a cycle that demands the Yankees sign increasingly expensive and old free agents to field a team that is unlikely to play deep into the playoffs.

Last year the Yankees missed the playoffs by seven games, but rather than, for example, trade Robinson Cano, a player on the cusp of free agency to whom they did not even make a significant contract offer, to a contender in exchange for prospects, they persuaded themselves they were still in the playoff hunt and held onto Cano, who signed with the Seattle Mariners after the season ended. Today the Yankees are in a similar situation. They are only two games out of the wild card race, but have little chance of winning much in the post-season even if they manage to grab the last wild card. The last thing the Yankees should be doing is trading what few prospects they have to build around a core of talent that is largely old, injured or both, but that is precisely what they are rumored to be trying to do.

These differences in approaches between the Red Sox and the Yankees are among the major reasons why the Yankees have won one World Series in the last decade while the Red Sox have won three. The Red Sox are able to recognize when a season is lost and reboot for the future while the Yankees are not.

The Yankees have never considered making those kinds of decisions. An aging Mark Teixeira, when healthy, for example, would be valuable to many teams looking for some power at DH, first base or off the bench. Veteran starting pitchers going back to Mike Mussina late in his career could have brought the Yankees good prospects in return, but the Yankees have never even considered being a seller at the trading deadline. The result of this is that the Yankees struggle and spend more money to play slightly over .500 while never having the flexibility and options afforded by a good minor league system.

Because the Yankees both refuse to ever recognize that sometimes it is not their year and persistently overvalue their own players, they end up with very little roster flexibility. Going into this season it was clear to most observers that Derek Jeter, Alfonso Soriano and Teixeira, even when healthy, were no longer the kind of players who could anchor a championship lineup, but the Yankees, either because of leadership that is five years behind the time or a fan base that forces the team to make poor decisions, were not able to accept that. Therefore, they added free agents and overestimated their chances, and are now in a position where, if things go right, they could get the second wild card and very likely an early exit from the playoffs.

The biggest Yankee weakness in recent years has been their farm system, other than aging stars and middle relievers, the only important player on the current team who is a product of that farm system is Brett Gardner. Moreover, the Yankees have no top prospects who will be ready for the big leagues in the near future. This is a big problem, but one that is made worse by an unwillingness to ever trade a veteran to help restock their farm system. The Red Sox and Yankees are an interesting rivalry in that they are both big spending teams with huge, loyal and to outsiders, annoying fan bases. They also have very different philosophies about building winning teams. Over the last decade, the Red Sox philosophy has proven to be the better one.