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Jon Lester Will Cash in on Clayton Kershaw’s Contract Extension

January 16th, 2014 at 11:30 AM
By Ron Juckett

'Jon Lester' photo (c) 2013, Keith Allison - license: http://creativecommons.org/licenses/by-sa/2.0/

The Los Angeles Dodgers have taken ace pitcher Clayton Kershaw off the 2015 free agent market Wednesday by extending the 25-year-old a whopping seven-year extension worth $215 million. On top of that, Kershaw earned an opt-out clause to trigger after five years.

Yes, boys and girls, Kershaw could be a free agent again at 30.

If the Dodgers figure Kershaw is worth $30.7 million a year, what would Boston Red Sox ace Jon Lester get on the open market?

Lets not fool ourselves and think Lester is going to get that kind of coin, even if he does win 25 in 2014, but with all the new television money burning a hole in the pocket of this generations big-spending owners, a deal that could see Lester in the $22-$25 million range is not out of the question.

Would that be an overpay? Oh yeah.

Is that what the Red Sox will offer? Not at this point. Here is why:

Make no mistake, Lester will be offered a long-term deal by the Red Sox that will make some of the faithful reach for the air-sickness bag. Expect it to be in the neighborhood of five-years and $100 million, right at $20 million a season.

Yeah, that seems like an overpay, but consider that Masahiro Tanaka, who has never thrown a major league pitch, is going to get a deal that will pay roughly the same amount of annual salary. In fact, count on Tanaka to get a six- or seven-year deal wherever he goes. That is $120 million, at least, for a pitcher that is a pure lottery ticket.

With new national and local television deals in place for all the big market teams, salaries are about to explode again, with Kershaw’s big deal setting the pace. The price to keep Lester, even with the hometown discount has gone up.

If Lester hits the open market, all bets are off as to how much the left-hander can command with willing owners in Los Angeles, New York, Seattle, Texas and Chicago offering what amounts to a blank check. The $20 million he would make pitching in a Red Sox uniform is cheaper and preferable to watching him return in Angels red or, worse, New York Yankees pinstripes.

What has not changed, on the other hand, is how long the Red Sox pan on keeping the lefty around for. If Lester wants the six-year extension, Boston will relent, even if there is no vesting option attached.

Unlike Jacoby Ellsbury, both sides want to have a deal done. With Kershaw resetting the market on the going rate of ace pitchers now, the Red Sox are now needing to spend $10-$15 million more to keep Lester than they would have a week ago.

Welcome to the 21st century version of the salary game.

Tags: Baseball, Boston, Boston Red Sox, Clayton Kershaw, Jon Lester, Los Angeles Dodgers, Masahiro Tanaka, MLB

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