Jon Lester rumors: Will Red Sox up offer to sign Lester?

Jon Lester is set to get a big contract as a free agent this winter. Is there any chance that he signs that deal to return to the Boston Red Sox?

It was the reunion that many people assumed was a sure thing when Jon Lester was dealt to the Oakland Athletics at this year’s trade deadline: Lester would come back to the Red Sox as a free agent.

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That made sense as far as the mutual admiration between the two sides, but not necessarily in terms of the mechanics of the actual deal Lester is seeking. Part of the reason that the Red Sox did not make enough traction on an extension for Lester was because they did not want to offer a fifth year in any deal. With that, the idea of Lester returning to the Red Sox has cooled significantly in recent months.

The Red Sox maintain that stance as far as the length of a deal, wanting to avoid a longer commitment with Lester or any other starting pitcher for that matter. But if they want to sign one of the big free agent starting pitchers this winter, they might not have a choice.

If it’s going to take a fifth year to land a guy on the level of James Shields, should the Red Sox just give in and turn their attention to Lester? That is the question posed by Scott Lauber of the Boston Herald:

"The pitching-needy Sox will undoubtedly try to lure Shields by hiking the average annual value of their best offer to at least $20 million in exchange for shortening the contract to no more than four years. But if that doesn’t work, and if the price for Shields will require principal owner John Henry to break with his preference for avoiding five-year contracts for over-30 pitchers, then why not just kick in an extra years or two and another $50 million to bring back Lester?"

There are two different issues for the Red Sox here: what they would prefer to do and what they can afford to do. Even if it is a little uncomfortable, the Red Sox can likely afford to add that fifth year. It will be interesting to see if they feel enough pressure to make such an offer to Lester or some other free agent pitcher this winter.

Lester was nothing short of outstanding this season, going 16-11 in 32 starts with a 2.46 ERA and a 9.0 K/9 mark.