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The Jon Lester trade winds continue to whirl, and while the exact suitors involved haven't quite been established, those in the know sense Lester won't be a Boston Red Sox pitcher by the end of the week.
The Sox seem to think they can get more for the impending free agent (and other players) now, via trade, than would be returned as compensation if he were lost in free agency, according to ESPN's Buster Olney:
Executives who have dealt with the Red Sox believe they will trade Jon Lester (and others) before Thursday's deadline, because they can extract more value now than they would by taking a compensation draft pick if Lester were to sign with another team as a free agent in the fall. Boston is asking for a high-end prospect to anchor a deal that would involve other prospects.
Beyond that, Olney also cites a "friend" of Lester who says "there is no chance" Lester would re-sign with Boston now (the sides are thought to be far apart, anyway).
While your mileage may vary on such rumors, especially given inconsistent information about the likelihood of a deal, it's pretty clear that the Sox are committed to moving their biggest trade chip toward the end of a lost season. The team has a contingency plan in case the lefty is dealt prior to the deadline.
Sorry, David Ortiz.