Jon Lester signs a long-term contract with the Red Sox
Lester hasn’t even turned 30 yet—he will hit that milestone January 7—and he’s already spent a dozen years in the Red Sox organization, having been drafted in 2002. He’s had many more ups than downs, but we’ve watched him overcome adversity to become one of the great lefthanders in Red Sox history, and one of the best postseason pitchers (2.11 career ERA in 13 appearances) of his generation. Lester, a free-agent after this season, is positioned to be a Red Sox lifer, particularly if he’s willing to sign for a little less than contemporaries such as Zack Greinke and Cole Hamels got in recent years. The hunch here is that a five-year deal in the vicinity of $110 million gets done in late February.