Ben Cherington talks Jon Lester extension

Jared Wickerham

With Jon Lester still not signed to an extension, are the Red Sox preparing for a future without their home-grown lefty?

Ben Cherington, speaking on the Dennis and Callahan show Thursday morning, did his best to explain what exactly was keeping the Red Sox and Jon Lester from agreeing to a new contract. He met with...mixed results.

He's got a lot going for him, and he's just a few months from free agency at a time when you and we all see what's happened with starting pitching in the free agent market and contracts have come down over the past two, three years. That segment of the population has clearly moved at least in terms of free agent dollars, so that creates a dynamic when you're trying to work on a contract.

...

We will work as hard as we can to try to make that work, but there's things that other teams might do that we just won't do. ... We're just going to keep working at it. While we're not currently, we'll be working on it at the right time and when there's a desire on both sides there's always a chance.

So, what's Cherington really trying to say here? Let's try to crack the code.

1) Free agency is bonkers!

Free agency prices are always on the rise. That's just the nature of things. But it's gotten a bit out of hand of late. Masahiro Tanaka raked in $150 million without having thrown a pitch in the majors. Zack Greinke is pulling in $24 million a year for the rest of the decade. And let's not even get started on what the Dodgers forked over to Clayton Kershaw just to avoid the whole process. The best of the best get an insane amount of money.

2) ...But not for everyone

What happens when you get past those best-in-the-business names, though? Well...Matt Garza signed for four years and $50 million. Anibal Sanchez one year before for five years and $80 million. Neither deal is small, exactly, particularly not the latter, but there's a very clear divide between top tier and the next rung down. And then every year there's the guy who lingers. Edwin Jackson, Ervin Santana....Supply has simply outpaced demand of late.

3) Lester falls in tier two

No, Jon Lester and Matt Garza is not a fair comparison. But it's also clear that he's just not on the same level as the first tier players. And there's not much question that Max Scherzer will be the man headlining the pitching market come November. That's with players like Ervin Santana, Justin Masterson, and James Shields all set to hit the open market at the same time.

4) If someone wants to treat Lester like he's in tier one, he's gone.

The Red Sox want to keep Lester. He's the guy they know, and that means no worrying about a new face having issues adjusting to Boston or Fenway.

But they also know that Lester is, realistically, not their only option. If he wants to stay on at a price around, say, Anibal Sanchez', then that's probably in play. If he thinks he can get more elsewhere, though, then the Red Sox have some very interesting options as mentioned earlier. Maybe that means going with James Shields, assuming his age means fewer years. Maybe that means a return for Justin Masterson, who probably comes in closer to Garza levels.

Whatever the case, it probably doesn't mean shelling out $100 million for Lester. And certainly not any figure significantly above that.

As always, we're stuck in the dark. Where does Lester see himself falling into that hierarchy? What does a "home town discount" mean to him? The fact that there's no ink on the dotted line yet suggests that the situation isn't as cut and dry as we all might want it to be. And the fact that Ben Cherington is saying things like "there's always a chance" doesn't exactly inspire confidence

Each side said all the right things in spring. It seemed certain to happen. But now? Now it's not nearly so clear.

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