When the Red Sox shipped Adrian Gonzalez, Carl Crawford and Josh Beckett to the Dodgers last year, they cleared a little more than $260 million in guaranteed contracts off their books. It was the salary dump to end all salary dumps, and that they happened to land a couple of flame-throwing pitching prospects was just a nifty bonus. The primary motivation for the deal was to recoup the money they'd spent, giving them a chance to reallocate those dollars in a more effective fashion in the future.
This winter, that future is going to become the present. The Red Sox spent last winter redistributing their newly available cash to quality role players on short-term contracts, and, after this season ends, the team no longer will have any further commitments to the likes of Mike Napoli, Stephen Drew or Joel Hanrahan, and only Dustin Pedroia, Clay Buchholz and Shane Victorino are signed through the 2015 season. Even after acquiring Jake Peavy at the trade deadline, the Red Sox are still expected to have approximately $40 million to spend this winter, and there are going to be opportunities for the team to put that money to use.
The primary decision, and the one that will shape what the rest of Boston's offseason will look like, will require an in-depth look at Jacoby Ellsbury's value.