‘Well-Connected’ MLB Executive: Jon Lester, Red Sox Headed For Reunion

At least one person expects Jon Lester and the Boston Red Sox to reunite.

A “well-connected baseball executive” on Monday predicted Lester will re-sign with the Red Sox in free agency this offseason, according to ESPN.com’s Gordon Edes.

It should go without saying, but the executive also thinks Lester might land a long-term contract, which would be a variation from Boston’s usual desire to not sign pitchers north of 30 years old to lengthy deals. The executive, according to Edes, did not rule out a six-year offer worth at least $20 million annually.

This obviously should be taken for what it is: a prediction. But the idea of Lester returning to the Red Sox is interesting, regardless, as it’s rare to see a player traded midseason return in free agency after the season.

Neither the Red Sox nor Lester has ruled out a possible reunion. Red Sox general manager Ben Cherington recently said he’s confident the sides will have a constructive conversation, as there’s nothing in their relationship that would prohibit Lester from re-signing with Boston if a deal makes sense.

The Red Sox definitely need to shore up their starting rotation. Re-signing Lester would go a long way toward accomplishing that goal, though the 30-year-old left-hander figures to come with a high price tag.

Thumbnail photo via Kim Klement/USA TODAY Sports Images

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