The Red Sox are going to have an open rotation spot heading into 2015, when Jake Peavy either leaves as a free agent or retires as he has hinted could happen. Should Jon Lester take off as well when his contract is up -- as unlikely as that might seem -- there will be a second open rotation spot. Boston has the prospects to fill both holes if there is indeed a pair, and could realistically have even more arms ready for it. At the same time, however, prospects do falter, and it's just as easy to believe that the arms closest to ready right now both find themselves better suited for relief work a year from now.
With that in mind, it's fair to consider if the Red Sox should bring back one of their former prospects, Justin Masterson. The Indians right-hander, dealt to Cleveland back in 2009 in the Victor Martinez swap, is looking more likely to be a free agent now that the Indians rejected his modest three-year extension proposal that would have paid him $17 million annually. Now's now the time to get into how surprising it is that Cleveland would reject the proposal of a pitcher who was not looking to be locked up for eternity, but instead is the moment where we wonder if this is something the Red Sox can take advantage of come next off-season.
Let's set the stage where Masterson might be necessary for the Sox. The Red Sox and Lester are very likely to enter into an extension with one another given their not-so-secret affinity for one another, but let's consider that the deal never gets done because the Red Sox won't add that extra year or that few extra million per season that Lester, who is already willing to pitch for a discount, is entitled to. It can happen, as you know, since such a thing is exactly what has Masterson set for free agency himself. Without Lester or the $20 million or so per year it would take to retain him on the books, the Sox would have both the rotation spot and the financial space to acquire Masterson. While Masterson has been a bit inconsistent in his career, he took serious steps forward with strikeouts -- crossing the one per inning threshold -- and against the lefties who once plagued him in 2013, thanks to changes in his approach that saw him pitching inside in a much more dedicated and successful manner. Getting to work with John Farrell -- his former pitching coach -- and his staff would be unlikely to impede on that progress.
Remember, too, that he has all of 2014 to show that his performance was for real, and not a one-off. He might not completely replace Lester atop the rotation, but Masterson has the capability to be a durable number two starter, something the Sox are going to need during this transition period for the rotation.
Even if the Sox do re-sign Lester, there could be room for Masterson in the rotation. Again, a spot is opening up when Peavy departs, and the likely replacements are Brandon Workman or Allen Webster at this time. Both of these pitchers -- and another pitching prospect, Anthony Ranaudo, who desperately needs a working change-up -- might not be big-league starters. They have the stuff, but the quality of their command remains a question, and if it doesn't improve or become more consistent, there is a chance one or both could spend their major-league careers in the bullpen. As assets in the bullpen, mind you, but still of no help to the rotation.
The Red Sox would have all of 2014 to see this, too, so it's not like it's a decision that would need to be made today with the information known right now: maybe Workman and Webster both take that extra step, and fight it out to be in the rotation next spring. Maybe one of them does and the other does not, but that's enough. Maybe Matt Barnes handles Triple-A much better than Double-A, and doesn't need to wait until 2016 when John Lackey's time in Boston is over in order to earn a big-league spot. A whole lot could change, so this isn't saying that Masterson has to be signed: it's simply just one more option to consider, depending on how well the prospects develop during the upcoming season.
Whether Masterson would want more than the three-year deal he offered the Indians is unknown, but if it had to be bumped up to four or even five, depending on how his 2014 goes, it could still be a quality play by the Sox. It might all turn out to be pointless for a number of reasons -- accelerated prospect development, Lester re-upping, Masterson and the Indians coming to terms despite this setback -- but it's worth thinking about in the interim.