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Jon Lester contract: Red Sox plan to continue extension negotiations

Lester might still become a free agent after the season, but the Red Sox hope to keep him in Boston.

Greg M. Cooper-USA TODAY Sports

Boston lefty Jon Lester is set to become a free agent after the season, but Red Sox CEO Larry Lucchino expressed his club's intention to pursue an extension with the two-time All Star on WEEI's Dennis and Callahan Morning Show. Lester has indicated that he's like to remain with the team, claiming that he'd take a "hometown discount" to do so.

On the open market, Lester would be one of the most-sought after players available. Alongside James Shields and reigning American League Cy Young winner Max Scherzer, Lester would represent one of the best free agent pitching pools in the last several years.

At his best, Lester is an ace. From 2008 to 2011, he posted a 3.33 ERA in 128 starts -- over 800 innings -- and struck out 784 hitters while walking just 288. Over that stretch he put up a tradition win-loss record of 65-32, but perhaps more importantly, the Red Sox won 80 of his 128 starts.

The team offered Lester an extension worth $70 million over four years in April, according to Yahoo's Jeff Passan. The 30-year-old could almost certainly do better than that in free agency. It's possible that he could land a $100 million deal on the open market, so the Red Sox might have to step up their offer to retain him. However, Lucchino said the $70 million figure was only a "starting point," so the two sides will presumably continue to negotiate a deal in hopes of agreeing before Lester is eligible to file for free agency after the World Series.