Jon Lester will always be viewed as the one who got away from the Red Sox -- but it doesn't appear that the lefty will be the one who returns to Boston.
According to WEEI's Rob Bradford, the Sox haven't expressed interest in a reunion with Lester, who hit free agency when the Cubs declined his $25 million option for the 2021 season.
Even though the Sox need starting pitching, there are pretty good reasons why Chaim Bloom is focusing his search elsewhere. Lester turns 37 in less than a month and has seen his ERA balloon in recent seasons, from 3.32 in 2018 (when he tied for the NL lead with 18 wins), to 4.46 in 2019, to a career-worst 5.12 over 12 starts last season.
Lester, who stands seven wins shy of 200 for his career, has expressed interest in returning to the Cubs, saying this earlier this offseason: "I know there is some doubt as far as the money that's out there, but I would like to think we can definitely get this thing done."
But for the Red Sox, a reunion with a pitcher who was a two-time World Series champion in Boston would be a storybook ending, especially after John Henry admitted the team blew it in contract negotiations with Lester as he was entering the final year of his Sox contract in 2014. Our John Tomase laid out the case for a Lester return in September.
In a slow-developing MLB offseason, there's still plenty of time for the Red Sox and Lester to find their way back to each other, but for now at least, the reunion looks unlikely.