Ben Cherington hopes to meet with Jon Lester

On August 13, 2002 the Boston Red Sox signed left-hander Jon Lester after drafting the Tacoma, Washington native in the 2nd Round of the 2002 Amateur Draft. Lester made his major league debut with Boston on June 10, 2006 at age 22 and had been with the club since then. However, this past July 31st, after 8 years and two World Series championships with the Sox, the ace was traded to the Oakland A’s along with outfielder Jonny Gomes in exchange for outfielder and power bat Yoenis Cespedes.

The A’s fell to the Kansas City Royals in a marathon AL Wild Card contest, ending their postseason run and leaving Lester up for grabs as a highly desirable free agent.

Lester could pull in some big bucks and become one of the highest paid pitchers in the league. The 30-year-old will have numerous long term contracts to choose from, and general manager Ben Cherington confirmed the Red Sox will be in contact with Lester:

"Again, we’re going to try to build the best team we can, and that is one of the areas we need to add to, the rotation. We know him well and hope we get a chance to talk to him. I’m sure he’ll talk to others and I’m sure we’ll talk to others. We just have to get into the offseason and see what comes of it.The relationship is in place that will allow for a conversation, and from there, we’ll see. He’ll have options; we will, too. And we look forward to having a constructive conversation at some point."

Following his trade, the ace spoke with John Tomase of the Boston Herald: “In the greater scheme of things, we’re talking about just a stupid amount of money,” he said. “For me, I want to be comfortable.” At best, the Red Sox would most likely offer Lester 7yr/$150M

Lester left Boston on good terms and has shown no signs of slowing down since he departed.  At the end of the season, Lester finds himself highly rated among baseball’s A (or ace) list, ranked as the number six starting pitcher in the league.  He finished 2014 16-11 with a 2.46 ERA in 36 starts and a 220/46 K/BB ratio in 220 innings.

It would be quite the feat if the Red Sox could trade Lester for Cespedes and then re-sign him.  The offseason will tell just how effective Cherington’s meetings with Lester will be, as well has how ‘comfortable’ Lester decides to be.