Jon Lester rumors: Red Sox unlikely to sign Lester in free agency

The Boston Red Sox had a lot of time and a lot of different chances to sign left-handed starting pitcher Jon Lester to a multi-year contract extension.

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If they had wanted to offer him more than the four years and $70 million that they already offered him, they probably would have done it well before they dealt him to the Oakland Athletics at the MLB Trade Deadline. But even with that being the case, common sense has not yet prevailed and many interested observers are still hoping for a reunion this winter.

Tim Benz of WEEI re-emphasizes the overlooked point here. If Lester was going to get an extension offer from the Red Sox, it would have happened. They are not going to somehow up their offer when the off-season arrives.

"I’m a huge Lester fan. Here’s the problem, though: Both sides need to want a reunion. And I’m not sure either side really does. Words says they both do. Actions say neither does."

Some team is going to pay Lester far more than the Red Sox are willing to offer. Even if Boston is suddenly motivated to increase their figure slightly, how much money would Lester actually be willing to leave on the table?

Nick Cafardo of the Boston Globe points out the simple truth that it is not fair for anybody to expect Lester to take less money to return to Boston, no matter how much he loved it there.

"The fact he wanted to see it played out in free agency tells me he wants to see what’s out there. He’s going to get six and seven-year offers at close to $25 million a year. Does he leave about $50-$60 million on the table? If he’s willing to do that, terrific."

Furthermore, Lester is not subject to a qualifying offer and therefore can hit the free market without limitations. That is an awfully nice opportunity for a legit stud pitcher to cash in a big deal.

It is a nice thought, something comforting for Red Sox fans and players alike to ponder, but it’s just not going to happen. Jon Lester is not signing with the Red Sox this off-season as a free agent.