Did Boston Red Sox Make Mistake Not Re-Signing Jon Lester Earlier?

By Steve Buchanan
Anthony Gruppuso-USA TODAY Sports
Anthony Gruppuso-USA TODAY Sports

Reports have been surfacing that the Boston Red Sox are now reengaging talks with Jon Lester in an attempt to re-sign him. The real question is, did they miss the boat on their chance to get a new contract for Lester?

Lester has done what every free agent to be does, have a phenomenal season prior to free agency to build off of. Teams always look at their prior season and assess what that free agent should earn. Lester has certainly done his part by owning a 2.92 and a 9-7 record. With those type of stats, teams will really be taking a hard look at Lester in the offseason. If, and this is a big if, he reaches that point. The Red Sox are doing what they can to avoid that situation. But, in my opinion, it’s too late.

With the type of stats and year Lester is having, he would be foolish to sign a contact with the Red Sox. In their first round of talks, the Red Sox offered a four-year, $70 million dollar contract. In this day and age, a somewhat of a bargain for a pitcher of Lester’s caliber. Supposedly, that offer and what Lester was looking to earn was “way off.” In my mind, Lester is most likely looking for something in the range of five years and $100-110 million. A contract I truly believe he could earn in free agency.

The problem with the Red Sox trying to get a deal done with now is that Lester could very well want to wait until the offseason to discuss a contract. Trying to get a deal done mid-year provides a distraction and can honestly hinder the performance of said player. The last thing the Red Sox need is to distract their No. 1 starter.

If the Red Sox lose Lester, it’s not because they didn’t do their part to sign him. They 100 percent made an effort to re-sign their star player. However, the effort they made wasn’t complete. Their attempts to keep contracts short and cheap will come back around to bite them. Case in point, the disappointing 2014 season for them so far. It’s a scary to think what the Red Sox could be next year without their ace. You thought this team was bad now? Yikes.

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