Is Trading Jon Lester A Realistic Option For the Boston Red Sox?

By Steve Buchanan
Winslow Townson-USA TODAY Sports
Winslow Townson-USA TODAY Sports

I touched upon this subject briefly yesterday: the thought of the Boston Red Sox trading their top starting pitcher in Jon Lester may actually make more sense than most people think. Lester is an impending free agent next year and will surely be one of the top free agents on the market if the Red Sox don’t resign him. As the losses keep piling up and the division starts to become more of a pipe dream, we have to consider all the options the Red Sox have. Even if you aren’t a fan of the idea, just bare with me for a few and let’s go over this logically.

Everyone wants Lester back on the Red Sox. This has nothing to do with his character or the way he performs. He’s an ideal pitcher, quite honestly. He goes out to the mound, does his job, takes responsibility for his own actions, and leaves. Perfect. He’s great in the postseason, holding a 6-4 record with a 2.11 ERA with 68 strikeouts in 76 innings. That’s exactly the type of guy any team would want in the postseason to start a Game 1, or even better, a Game 7.

So, with the Red Sox postseason dreams becoming more and more distant, a decision will have to be made about the future of Lester in a Red Sox uniform. Is there a realistic chance that a new contract can be drawn up to the liking of both sides? If not, then the Red Sox need to cash in on the only other option, which is trading away their star. The ransom they could receive for Lester could be huge. A major league-ready player and two prospects seems logical. A package of prospects could also be viable. Even though Lester is an impending free agent, teams will pay the premium for that star player at the deadline. It’s happened many times before.

I think a team in the National League would be a perfect destination if a trade were to be done. I see a few teams that are literally one star pitcher away from being able to lock up a playoff spot. Teams like the Colorado Rockies, Los Angeles Dodgers, or even the Pittsburgh Pirates, who could really make a splash at the deadline. All these teams could use a boost in their rotation to really put them over the top. Could you imagine playing a five-game series against the Dodgers and getting Clayton Kershaw and then Lester? Oh mama.

One final thought — and again, this could be a long shot — but even if the Red Sox trade away Lester, the possibility of re-signing him in the offseason is still plausible. Think about this huge package the Red Sox could receive, only to re-sign him months later. Pure brilliance. But that’s a pipe dream.

The next few weeks will be a true testament of where the Red Sox will stand come July 31. August 1st will show where they stand in the Lester saga. Will he stay, or will he go?

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