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Red Sox, Lester talking extension

The Red Sox have reportedly entered contract negotiations with longtime ace Jon Lester.

Jim Rogash

The Boston Red Sox appear interested in holding onto impending free agent southpaw Jon Lester, having already entered extension talks with the two-time All-Star, according to Nick Cafardo of The Boston Globe. Lester is set to be a free agent at the end of this season.'s Jon Heyman spoke with Lester regarding extension talks, and Lester expressed a clear desire to stay in Boston, stating "I don't like change. I like being where I've been, I like the people. I like the surroundings. It feels like home."

Added optimism that a deal could get done comes in the form of Lesters' agents, the Levinson brothers (who have been spotted at Red Sox camp in recent days). According to Cafardo, the Levinson brothers have been advising clients to take below-market deals if they're content with where they are. Last July, under the advisement of the Levinson brothers, Lester's teammate Dustin Pedroia agreed to a eight-year, $110 million extension, a sum which many saw as a significant discount for Boston. The Levinson brothers also helped orchestrate David Wright's $138 million extension with the Mets in the winter of 2012, another deal which some saw as a hometown discount.

Lester is set to make $13 million this season in the final year of a six-year, $44 million deal he signed with Boston prior to the 2009 season. The 30-year-old former second round pick bounced back after a down 2012 season to go 15-8 with a 3.75 ERA (3.59 FIP), 2.64 SO/BB, and 4.3 WAR in just over 213 innings. He averaged a 5.0 WAR and 135 ERA+ in 203 innings pitched per season from 2008 to 2011.

In the past two years, a number of pitchers, similar in both performance and age to Lester, have signed long-term contract extensions in the year before they hit free agency. Adam Wainwright signed a five-year, $97.5 million deal with the Cardinals last March, and he was only one year removed from missing an entire season due to Tommy John surgery. Matt Cain and Cole Hamels each reached six-year extensions with their respective clubs before the 2012 season, preventing them from becoming free agents at the end of the season. Cain and Hamels each profiled quite similarly to Lester and they each garnered deals worth at least $130 million, a total which Lester would likely command were he to reach the open market.

Just last month, Homer Bailey agreed to a six-year, $105 million (with a $25 million mutual option for 2014) deal with the Reds. While Bailey is over two years younger than Lester, he has only been an above average starter for two seasons now, and he hasn't approached the numbers Lester put up during his remarkable 2008-2011 stretch.

Source: FanGraphs -- Adam Wainwright, Matt Cain, Jon Lester

If Lester does decide to test the free agent market at the end of the season, he would be joining a starting pitching crop that figures to be headlined by Max Sherzer, James Shields, and Justin Masterson (assuming none of them sign an extension between now and November).