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What the Clayton Kershaw Contract Means for Jon Lester

Jon Lester

Yesterday it became official, the Dodgers extended Clayton Kershaw to a monster 7 year $215 million dollar contract. The $30.7 million AAV trumps the previous record one year $28 million dollar contract signed by Roger Clemens in 2007. The one thing that is different from all these other large contracts is that Kershaw is probably worth it. He is still just 26 years old and led the league in ERA for the past three seasons. He is durable as well, the last time he didn’t pitch 200 innings was his first full season when he was 21. Kershaw got his money and will no longer be a free agent after this season.

So what does that mean for Jon Lester and the Red Sox?

For one thing, Jon Lester will not come close to the $30.7 million AAV. Kershaw is a once-in-a-lifetime pitcher, someone who has the capability to be mentioned with the likes of Sandy Koufax and Greg Maddux. Lester is a good pitcher but he is not legendary. While Lester will not command the same salary, Kershaw’s deal will affect his contract. With Kershaw no longer a free agent the top two pitchers on the market are Jon Lester and Max Scherzer. With fewer options on the market, Lester may be able to command a much larger contract, think Zack Grienke money (6 years $147 million).

Given that the Red Sox have shied away from long term contracts, it would seem that Jon Lester is not destined to stay in Boston, but not so fast. Jon Lester has said several times that he wishes to remain in Boston and seems to be amicable to a hometown discount. The Red Sox also have more than $75 million coming off the books after 2014 and will have money to spend. They have shown a willingness to extend homegrown players (Dustin Pedroia) and Jon Lester may be next. A 5-year, $100 million dollar contract may be a middle ground that both the Red Sox and Lester could agree upon.

The best case for the Red Sox would be to sign Lester before he hits free agency. Once he hits the market, competing with the other offers out there will be difficult for the frugal Red Sox. Here’s hoping they can figure it out before it gets to that.

About Jamie Worthington - @Jam_Worth

Jamie is a regular contributor and editor for Sports of Boston, but has thoughts for all Boston areas sports for SoB. He loves that in sports everyone is allowed to have their own opinion and wants to hear yours! Follow him on twitter at: @Jam_Worth

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