With the Red Sox firmly entrenched in The Land of Crappy Baseball (to put it mildly), it's become more clear than ever that they should be sellers at the trade deadline. One big exception to the sell, sell, sell mantra is Jon Lester. Jon Lester may not at the very top of the major league pitching pyramid and he has his drawbacks, but he's the best pitcher the Red Sox have at the moment and he is a proven post-season stud. The Red Sox may have a farm full of young pitching, but none of those arms currently projects higher than mid-rotation. Ergo, there is currently nobody to take Lester's place should he depart for free agency in the off-season.
Ben Cherington is a GM who is loath to give out long-term deals to free agents. His strategy may have worked in 2013, but most of the time it reads as small-market strategy that puts a team in perpetual rebuilding mode. The Red Sox are not a small-market team. They can afford to give out large, long-term contracts to the right players. The key is determining who the right players are. I believe that Lester is one of those "right players" and that failing to extend him is as good as fitting him with pinstripes. The Yankee way of relying on aging stars at the expense of developing the farm has its own problems, but a combination of developing young talent and ponying up for the proven veteran is a strategy that should keep a team contending most years.
If the Red Sox don't extend Jon Lester, which would be a huge mistake as far as I'm concerned, they could face a multi-year rebuild that would not go over so well with the fanbase. Some rebuilding is necessary, but waiting three or four years for a new frontline pitcher to establish himself, if that even happens, could mean more seasons just like this one. There are options on the free agent market, but the ones worth paying (i.e. Scherzer) would cost just as much, if not more, than the one who has proven he can handle playing in Boston and pitching in a hitter's park like Fenway.
As far as who the Red Sox can part with, the first to go should be A.J. Pierzynski. The return of the whining and excuse making that characterized the 2012 team under Bobby Valentine suggests that something is rotten in the Red Sox clubhouse. It may not be fair to dump all the blame on Pierzynski, but he came to Boston with a reputation for rubbing his teammates the wrong way. Peavy is next in line and his back-to-back quality starts should help his trade value. Lackey shouldn't be untouchable either. Gomes, Carp, Mujica, Badenhop, Breslow, and even Koji could be shopped. The prospect haul might not be that impressive, but it clears the way for some of the young talent on the farm to get their feet wet at the major league level. Some might not be ready for prime time, but this season is lost anyway. The Red Sox might as well see what they've got in some of those kids.
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