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Jon Lester May Return to Boston After All

Tony Consiglio

Tony Consiglio is a lifelong baseball fan and has worked for television and radio stations throughout New England.

When the Red Sox traded Jon Lester over the summer, conventional wisdom was that the lefty’s days in Boston were done. After all, the team was unable to sign him to a long-term deal while holding exclusive negotiating power. The two sides were reportedly not even close on their proposals. So now that 29 other teams can bid for Lester’s services, logic would seem to dictate that any chance of an extended stay in New England was all but over.

Not so fast.

According to ESPN Boston’s Gordon Edes, a “well-connected baseball executive who has had conversations on the subject with the Red Sox” predicts Boston will eventually land the ace. But it will likely take several years and a lot of money. That executive believes it could be for six years and at least $120 million. That’s a far cry from the four years and $70 million the organization offered him during the season.

A contract of that size contradicts the very philosophy the team adopted after the albatrosses that were Carl Crawford, Adrian Gonzalez, and Josh Beckett. Owner John Henry has publicly expressed his concerns with long-term deals for players over 30, especially pitchers. And in an interview with BusinessWeek in April, he said, “Virtually all of the underpaid players are under 30 and virtually all the overpaid players are over 30. Yet teams continue to extravagantly overpay for players above the age of 30.”

While it’s been the general public understanding that the Red Sox will avoid such deals under all circumstances, GM Ben Cherington has opened the door to the possibility this week, telling reporters, “It’s never been a hard policy. We’ve made exceptions, and I’m sure there will be another exception. It’s a case-by-case thing. If all the boxes are checked, sure, there will be a longer term deal. It’s just as we’ve done in the past.”

That sounds like an executive setting the stage for a potential big move. And if the Red Sox are going to make one, Lester would be the logical choice.

The fact that he is a known commodity within the Boston front office is important. Not only does the team know he can pitch in Boston, but management is more familiar with his health than they would be for any other free agent. Lester has been extremely durable, throwing more than 190 innings in each of the last seven years.

But, he’s only gotten better. He is coming off the best season of his career, and finished fourth in the Cy Young Award voting. The Red Sox could use a pitcher like that. Boston’s starting staff allowed more runs than all but three teams in baseball last season. Cherington traded away nearly the entire rotation, and while there are many potential front-line starters making their way through the Boston system, they aren’t ready to take on the role of the number one that the Sox need.

There’s even the chance the Red Sox won’t have to be the highest bidder for his services to get him back. Shortly after being traded to Oakland, Lester told reporters, “‘I don’t need to be blown out of the water. Why would I need to be blown out of the water? That doesn’t make or break your decision, at least for me. I’m not going to the highest bidder. I’m going to the place that makes me and my family happy. If that’s Boston, it’s Boston.”

And it might be Boston. WEEI’s Rob Bradford reports the Red Sox are one of six teams showing legitimate interest in Lester’s services. Cherington has already met with his agents, saying, “I met with them kind of socially and talked about all sorts of things. I expect the conversation will continue. They have to go through their thing. I still feel like the relationships are in place we can have those conversations.” And, the pitcher and his agents will even meet directly with Boston ownership within a matter of days, another sign the team may be plenty serious in its interest of him.

All things considered, it makes little sense for the Red Sox to not be aggressive in trying to re-sign Lester. The general philosophy of not signing aging players to long-term, big money deals makes sense, lest you become the Yankees. But, there doesn’t need to be a hard and fast rule against such signings, which Cherington has started to hint at this week. And, if there is going to be one player for whom to make such an exception this offseason, it should probably be Jon Lester.