Jon Lester wants to remain with the Boston Red Sox organization until he retires from the game of baseball. Heck, the 30-year-old starting pitcher has won two World Series titles in Beantown, so how you can you blame him? However, as 2014 MLB Opening Day nears, so too does Lester’s impending free agency.
Baseball players rarely drag contract talks through the season. Instead, most All-Stars like Lester decide to leave the bargaining for the offseason, where teams from across the league can outbid one another. Yet, Lester’s situation is rather different considering he has stated on numerous occasions that he’s even willing to take a hometown discount in order to stay in Boston.
Again, I will ask the question: What is Red Sox general manager Ben Cherington waiting for? If Boston manages to let Lester enter the free agent pool this winter, he would likely join fellow All-Star pitchers like David Price and Max Scherzer.
Cherington has done a fantastic job building the Red Sox starting rotation, but it would all be for not if the team is unable to sign Lester to a long-term deal. All of the pieces are in place for Boston to tag Lester with a team-friendly six-year deal, yet Cherington’s hesitation has some Red Sox fans worried sick and rightfully so.