on baseball

Jon Lester negotiations will be interesting

Looming free agent Jon Lester  was 4-1 in the 2013 postseason.
jamie squire/getty images/file
Looming free agent Jon Lester was 4-1 in the 2013 postseason.

In two years or less, the Red Sox may have another lefthanded stud in Henry Owens, who will be under their control for six years. They have righthanders Matt Barnes, Anthony Ranaudo, Brandon Workman, Allen Webster, and others on the way.

Posed this question on What do you do with Jon Lester, who is scheduled to become a free agent after the season? When the Red Sox and Lester start negotiating a new deal — likely to happen in spring training, according to a major league source familiar with the situation — do they go all out to sign him or watch how the season goes and make a decision toward the end of 2014?

What’s interesting is that many teams would have tried to tie Lester up already.


The Red Sox haven’t. Why?

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As a big-market club they can afford to wait a little longer than most. But as was the case with Jacoby Ellsbury, sometimes when they let it get to the end, they don’t get their man as Ellsbury wasn’t able to say no to the Yankees’ extraordinary offer.

What we don’t know in this case is whether Lester is willing to accept less than market value for his services to stay with the Red Sox, the way Dustin Pedroia did, or whether he expects to be paid top dollar, the way Ellsbury did.

The Clayton Kershaw deal obviously shows that the price of pitching is going up. Kershaw will average just over $30 million per year on his seven year, $215 million deal with the Dodgers.

You can argue Kershaw is in a league of his own, but where does Lester, who was 4-1 in the postseason, including 2-0 with a 0.59 ERA in the 2013 World Series and 3-0 with a 0.43 ERA in two World Series appearances, fit in?


One American League general manager indicated Kershaw shouldn’t have any bearing on negotiations with Lester, Kansas City righthander James Shields, who also will be a free agent after the 2014 season, or any pitcher.

“They may try to use that,” the GM said of the Kershaw deal, “but he seems pretty unique given his age, his awards and dominance. Those guys with a combination of age and dominance don’t exist.”

The one pitcher who may benefit is David Price. The 28-year-old lefty signed a one-year, $14 million deal with Tampa Bay Thursday, but if a team deals for him it may have to pony up a big number. Maybe not as big as Kershaw’s, but a significant one.

Lester, who had some ups and downs in 2011 and 2012, corrected those in 2013 and went 15-8. He’s 100-56 (.641) over his career and he just turned 30. If the Red Sox and Lester have begun talks, both sides have kept it quiet.

So will the Red Sox pay Lester a massive salary at his age, knowing they have a strong core of young pitchers developing in the minors, or will they decide, as they did with Ellsbury, that they will not commit long-term for that type of money?


Lester has said he’d like to remain in Boston.

It’ll be interesting to see how these negotiations unfold.

The Red Sox have never been afraid to extend core players. They did it with Josh Beckett. They did it with Pedroia. They decided not to do it with Ellsbury, who never got an offer from the team. They also decided against a long-term commitment to Jonathan Papelbon.

Lester has always been a dilemma for the Red Sox. On the one hand, he’s a multiple 200-plus-inning performer. The Red Sox don’t have many of those.

In fact, Lester was the only pitcher on the staff to reach that mark last season, extending himself to more than 240-plus innings through the postseason. What kind of wear and tear will that be on him?

Lester has been a horse throughout his career. He’s a proven money pitcher.

Suffice to say, when Lester hits the open market along with Shields, providing both have a strong 2014, they will be in demand. It’s conceivable $20 million per year or more will be in their future. It’s just the nature of the beast.

There will be teams lined up to pay it. With bigger TV deals and more payroll available, the big bucks are going to be devoted to pitching. So wouldn’t the Red Sox be one of the teams involved? Maybe they just don’t have to be.

Yes, Kershaw is unique, but some of the top pitchers in the game were better at 24 and 25 than they were at 30. Look at Felix Hernandez. He’s still an elite pitcher, but in his early 20s he was dominant, unhittable, and won a Cy Young. Now, he’s very good, but as he approaches 28, not lights out. It happened to Tim Lincecum, who seemed like he would have an amazing career. And he did when he was 24 and 25, but has fallen significantly.

Pitchers who continue to dominate are rare, unless they’re able to change their style of pitching to incorporate more finesse, guile, and wisdom as Greg Maddux and Tom Glavine did. That’s why those guys make it to the Hall of Fame.

We’re already seeing, at age 32, the wear and tear on Yankees lefty CC Sabathia. Pitchers are best before 30. There are exceptions to everything, but again, those examples are few and far between.

Even Justin Verlander has lost a little bit after pitching at age 30 in 2013.

So the Red Sox are probably thinking, especially the way they’re doing business now, that they’d love to keep Lester, but it will have to be on their terms. They’d love to keep him with a contract they can look at a few years from now and be happy with rather than a contract where they have to hold their breath and wonder if they’re going to eat a lot of money.

The Pedroia contract was front-loaded. The end of the contract doesn’t kill them.

It’s nice to be a World Series champion that has young, controllable pitching on the way. You don’t have to be held hostage, yet you have enough resources to do it if you want.

The Red Sox seem to hold all the cards when these talks get underway.

Nick Cafardo can be reached at Follow him on Twitter @nickcafardo.