Jon Lester To Red Sox? Whether Reunion Makes Sense For Either Side

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Will the Red Sox make a splash this offseason? Boston has financial flexibility and a strong desire to bounce back from a disappointing 2020. As such, we’ll examine whether several notable free agents make sense (or don’t make sense) as the club looks to retool for 2021 and beyond.

Baseball reunions often work better in headlines than they do in actual practice.

But could a genuinely worthwhile reunion be in the cards this offseason for Jon Lester and the Red Sox? It’s a storyline that’s impossible to ignore.

By now, you know Lester’s backstory: Eight-plus seasons, including two championships, in Boston, a mid-season trade in 2014 to the Oakland Athletics and then six campaigns, including another World Series title, in Chicago with the Cubs. The Tacoma, Wash., native, whom the Red Sox selected in the second round of the 2002 Major League Baseball draft, has had a fantastic career. He might be a Hall of Famer.

Story continues