Jul 15, 2014; Minneapolis, MN, USA; American League pitcher Jon Lester (31) of the Boston Red Sox throws a pitch in the second inning during the 2014 MLB All Star Game at Target Field. Mandatory Credit: Scott Rovak-USA TODAY Sports

Jon Lester "thrown off" by mid-season negotiations

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As the second half of the season is set to begin, one major question looms over the future of the Red Sox. Will the team extend ace Jon Lester?

Despite previous claims that the two sides would not negotiate this season, contract talks have picked back up in recent weeks. The Red Sox have reportedly resumed negotiations with the 30-year old, though those negotiations do not necessarily appear to be for the better. Lester said that he was “thrown off” by the Red Sox’ repeated attempts at a contract extension, adding yet another chapter to the saga of dismal ways that the Red Sox have handled Lester’s situation.

The Red Sox fully expected to extend Lester before this season even began, but lost all credibility when they low-balled him with a 4 year/$70M contract offer in March. Though that offer was absurdly low even then, it doesn’t help that Lester’s stock has risen significantly over the course of the season. Already the unquestioned leader of the pitching staff and a Red Sox icon, Lester is also posting a career year in 2014 as he currently stands at 9-7 with a 2.65 ERA supported by a 2.61 FIP, both of which are the best of his career. His 4.62 K/BB is by far the best of his career and is supported by his sinking walk rate, which has lowered in each of the past five seasons and now stands at a stingy 2.0 BB/9.

Those statistics point to Lester being paid like an ace, and an ace is exactly what he has been both in the 2014 season and the 2013 playoffs. While Lester reportedly would have accepted a contract “a shade over Homer Bailey‘s [6 year/$105M] extension,” that price has now risen far above that mark even if Lester is still willing to accept a hometown discount.

Lester is still saying all of the right things and upholds that he wants to remain in Boston. However, the Red Sox are going to need to pay up in order to make that work.

As a fan, I would love to see Lester remain in Boston. If he gets a five or six year deal and he delivers, then he absolutely has a chance to go down as one of the best pitchers in Red Sox history. However, it is generally considered poor negotiations to pay for a pitcher’s career year; unfortunately, that is exactly what the Red Sox must do in order to retain Lester. Hopefully the team will be able to lock him up this offseason; however, it does look like we’ll have to wait until then.

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