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Tony Massarotti

With Lester, History Suggests it's Over

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Barry Chin/Globe Staff


You can believe what you want to believe and there is certainly a good deal of time remaining, but if the past is prelude, Jon Lester is gone.

And so no matter what kind of rhetoric is spewed over the next weeks and months – from both sides – remember to judge people by their actions and not their words.

In case you somehow missed it, Red Sox owner John Henry sent an email to the Boston Herald earlier this week declaring that contract talks between the Red Sox and Lester have been put off until the end of the season. Lester.jpgIn theory, that still leaves plenty of opportunity for the sides to come together, for fences to mend and minds to meet, for the Red Sox and Lester to come to terms on a deal that will keep the pitcher in Boston for the 2015 season in beyond.

In reality, there is a lot more cause for doubt than there is for trust.

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Go back and look at the list of notable Sox players who come through here over the last 12 years, the period of time that coincides with Henry’s ownership of the club. Pedro Martinez. Derek Lowe. Trot Nixon. Johnny Damon. Jonathan Papelbon. Jacoby Ellsbury. Victor Martinez. Jason Bay. For the most part, all of them performed reasonably well at the end of their contracts with the Red Sox.

And all of them hit free agency and never looked back.

Yes, the Red Sox had more interest in some of those players than others. Guys like Nixon and Lowe were never really considerations. Guys like Bay and Victor Martinez might have been pawns that the Red Sox deftly manipulated under the terms of the old collective bargaining to accrue compensatory draft picks. (One out, two in.) But the point is that when the Red sox have truly wanted a player, they have signed him early.

And the evidence is overwhelming.

Dustin Pedroia? He has never hit free agency and probably never will. Clay Buchholz was signed years ago. In 2006, when he was far closer to the prime of his career and potentially headed to free agency, the Red Sox signed David Ortiz to a four-year deal. Josh Beckett got an in-season extension – twice.

Hell, even Lester, like Buchholz, was signed to a multiyear contract during his arbitration years, the kind of what’s-good-for-you-is-good-for-me deal that the Red Sox have generally tried to explore with key players in their mid-20s. But once the player creeps north of 30, the Red Sox almost always start pounding the table and talking about risk, which is their way of saying thanks … but no thanks.

Before anyone points out the exceptions to this approach, we’ll do it for you: Ortiz has hit free agency much later in his career – when his options on the market have been more limited – and has re-signed. Jason Varitek stayed here, too, most notably following the 2004 season, when he signed a four-year, $40 million contract. Some of you might even include Mike Napoli, who re-signed last offseason. But the examples are relatively few and far between, and they have almost always come when the player has had relatively few options.

After all, Red Sox administrators are nothing if not good businessmen, and they know when they have the upper hand.

Right now, they don’t.

Which is why their failure to lock up Lester before the start of this season was the kind of mistake that makes you wonder whether they were reading their own press clippings (again) in the wake of a World Series championship.

So the Sox want to Lester go? Fine. We’ve all been through this before. But what’s the alternative? Three prospects and $96 million (his guaranteed remaining salary beginning in 2015) seems like a lot more to pay for Cole Hamels, who may not even be on the market. Maybe the Sox want to extend John Lackey, who will be 36 in October and is threatening retirement. (No risk there?) And even if Lackey is re-signed, that does nothing to replace Lester, who is younger and left-handed, and has been one of the most durable pitchers in the game during his career.

The bottom line: it certainly feels like the Red Sox have overplayed their hand on this one. They might have had Lester in the spring with an offer more aggressive than the four-year, $70 million laugher they presented, but they were intent on using Lester’s words against him (the dreaded “hometown discount”) to save a few million bucks. Nice strategy there. Let’s take the very first player we drafted in this ownership, a guy who has overcome cancer and won two championship rings while posting a career World Series ERA of 0.43, and pick a fight with him. He said he wants to stay. Let’s use it against him!

Dumb. Dumb, dumb, dumb.

Overall, once again, the Red Sox are smart businessmen. Maybe they have something up their sleeves here. Maybe there’s a blockbuster on the horizon that nobody knows about. But in new-record time, the Red Sox have once again destroyed much of the goodwill they earned from a world title, something they did in a mere four years after winning the title in 2007. This time it took only four months. And so unless the Sox intend on going through another transitional season next year – this time on their pitching staff – they need to find a replacement for Lester or they need to lock him up.

Based on recent club history, the latter doesn’t seem like a great option.