The Red Sox have multiple holes that people have been hoping they'll fill before the trading deadline on Wednesday. Primarily, those holes have revolved around the pitching staff, whether it be for a starter or a reliever. Another spot for which people have called for reinforcements is the left side of the infield. While I'm not convinced they are in need of any sort of boost there, it is certainly an interesting spot for this roster moving forward for the next few years. There is a lot of depth there in the farm system, but it is obviously uncertain whether or not that talent will translate at the big-league level. With all of the moving pieces that are able to fill two positions, Boston's front office has a few different courses of action to choose from. Whichever they choose, the goal will be maximizing value from every piece, whether it be in Boston or in the trade market.
To start out, the smartest move would be to stand pat for the remainder of this season at the position, and concentrate on adding an arm for the stretch run, preferably a reliever. For all of the grief he seems to get throughout the fanbase, Stephen Drew has been playing just fine when healthy. He's batting .228/.313/.413 this season, which is significantly above-average compared to the typical shortstop, despite the low batting average. His current wRC+ of 94 is 10 points higher than the league-average player at his position, and he's supplemented his bat with good play in the field. Jose Iglesias is coming back down to earth after his ridiculously hot start to this season, but that wasn't hard to predict given his sky-high batting average on balls in play. However, his performance this month isn't his true-talent level either, as his BABIP in July is just .246. It's hard to call his good performance unsustainable based on a high BABIP in a small sample, then turn around and criticize him based on a low BABIP in a small sample. He's also maintained his newfound low strikeout-rate, with virtually no change in that regard during this slump. Brock Holt, Brandon Snyder and (hopefully) Will Middlebrooks are perfectly suitable depth pieces for the stretch run. While a move for someone like Michael Young wouldn't be the end of the world, they should focus their energies elsewhere.
Now, despite everything that was just said about Iglesias, once the offseason begins the Sox should gut the current left side of the infield. Firstly, Stephen Drew is playing himself into being worthy of a qualifying offer. Good-hitting shortstops who can also play defense are rare, so he should fetch a decent contract in free agency, giving the Red Sox a compensatory first-round draft pick. Iglesias, on the other hand, will probably see his value as high as it's been in a few years. He's shown that he has the ability to hit major-league hitting, while also showing off the glove that everyone had heard about for years. The added versatility given his ability to play third as well certainly won't hurt. Because of this, I'd see if he could fetch a good return, perhaps from a team like the Cardinals or the Pirates, both of whom have long been looking for a shortstop. It wouldn't be absolutely necessary to deal him -- they should hold out for good value -- since he can be a utility guy moving forward if nothing else, but the shortstop position should really belong to Xander Bogaerts from the get-go next season. As we got a glimpse of in the Future's Game, his approach is mature beyond his years. If his glove is truly able to handle the shortstop position at the big-league level, then that's where he should play in Boston to maximize his value.
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Also in the farm system is Garin Cecchini, who could be ready to play third base as soon as 2015. While he's far from a sure-thing at this point, the Red Sox have to keep that option available, meaning a stopgap player would have to come in for third base next year. Ideally, that player would be Will Middlebrooks. If last year's breakout rookie could use the rest of 2013 to convince the organization that he is worth another shot at the starting gig in 2014, the Red Sox would be able to save their assets to fill other positional needs, like first base or catcher.
If Middlebrooks can't earn that spot back, the Sox are either forced to search outside the organization or keep Iglesias there again. To me, looking elsewhere is more appealing, though the free agency corp isn't at all appealing. The trade market does have a couple of appealing stopgap options who could enter the free agent market in 2015. Boston's surplus of pitching prospects could be a huge boon in that situation, assuming they don't gut that supply in the next couple of days. With the right package, they could very well be able to grab someone like Chase Headley from San Diego, who has taken a step back from his MVP-level play he showed in 2012, but is still a very effective player. If that turns out to be too hard to pull off, Aramis Ramirez could also be available to take from Milwaukee. Either one of those players could also be retained if something unforeseen happens to Cecchini and he won't be ready to contribute so quickly.
There are many different routes the front office can take with the shortstop and third baseman positions for this team besides the one I laid out as my ideal scenario. They could very well decide they don't want to lose Iglesias' glove and either keep him at third base or move Bogaerts there. They could also dip into the weak free agency class this offseason and take in someone like Young or even Kevin Youkilis, though asking him to play third again would be extremely risky. However they choose to do it, setting it up for a Bogaerts/Cecchini combo in 2015 by dealing Iglesias and finding a stopgap at third base seems to be the ideal route for the front office to take.