So as I'm sure you all know, the Sox have so far announced Tim Wallach and Brad Ausmus as managerial candidates, but their preferred choice is John Farrell. We have some questions to discuss.
What are the chances the Sox can persuade Toronto to part with Farrell? If so, what would be the compensation?
Who else would you like to see as manager of the Red Sox?
What are the chances they sign a recently-retired beloved Red Sox player? Mike Lowell has already said he does not want to manage, but what are the chances Jason Varitek or Tim Wakefield gets a look?
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Secondly, Ben Cherington has a lot to do this offseason. He'll have to make decisions on David Ortiz and Cody Ross, and I believe (as many others do) that Jacoby Ellsbury will either be extended or dealt this offseason.
Were you in Ben Cherington's shoes, what is the maximum extension you would give to David Ortiz? How about Cody Ross?
Would you even bother trying to deal with Ellsbury, a Boras client, when you have Jackie Bradley Jr. coming through the farm system?
Assuming you traded Ellsbury, would you try to get a package of prospects in return, or go for one of the young but established stars on the trade market, e.g. Justin Upton or Elvis Andrus?
What does Jon Lester's future in Boston look like? Is he still the ace, will they trade him for prospects, or will they keep him until his current contract expires, and let him walk?
Would you make a run on Hamilton, Greinke, or another free agent this offseason? (My instincts say no). If you did, what would be the maximum you would be willing to give them?
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Finally, no rebuilding project is complete without the farm system. The Sox have some excellent prospects down on the farm, including the "Killer B's" of Bogaerts, Barnes, Bradley, and Brentz. They've already seen the first of their prospects break through when Will Middlebrooks successfully made the leap earlier this year.
Bogaerts does not project defensively as a shortstop, and is blocked at third by Will Middlebrooks. There are thoughts of switching him to left field, where his bat will easily carry him, even if his defense reminds us of Manny Ramirez. Thoughts?
On the subject of shortstops, where does Iglesias fit into the Red Sox' future? Will his offense improve enough for his defense to make him an everyday shortstop? What is the offensive floor for Iglesias to contribute positively to the team? (For reference, Brendan Ryan hit like .180 for Seattle but was among the most valuable shortstops in baseball because of his defense).
Does Rubby De La Rosa project as a starter or a late-inning reliever? How about Allen Webster?
Where does Ryan Lavarnway come in? He showed nothing this September, and Saltalamacchia is very valuable defensively, whereas Lavarnway is a liability there. Should they try to teach him to play first base, where they can use his potent bat and fill up a hole in the infield?
Let us discuss.
