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Three years ago, Jon Lester signed with the Cubs

Rob Bradford
December 15, 2017 - 12:29 pm

Heading into the 2014 winter meetings, there was some optimism the Red Sox might be able to re-sign Jon Lester.

John Henry had visited Lester a few days prior at the pitcher's Georgia home, and it certainly appeared as though the Red Sox were going to go all-in to get their ace back. But then, in the middle of the night during the San Diego-based meetings, word came down the Cubs won the services of the lefty.

Chicago decision-makers Theo Epstein and Jed Hoyer had spent the majority of the previous night entrenched in hotel room negotiations with Lester's representatives, Sam and Seth Levinson, paving the way to what would be a six-year, $155 million deal that included a $25 million mutual option for one more season.

The Red Sox? Their offer fell well short. (Sources suggested, after the fact, if the Sox were remotely close Lester would have most likely been inclined to head back to Boston.)

The next day, the Red Sox filled out their rotation with trades for Rick Porcello, Wade Miley and Justin Masterson.

And on Dec. 15, 2014, Lester officially put pen to paper and was announced as the new foundation piece for the up-and-coming Cubs.

So, how has it worked out? From the Red Sox perspective, not great.

After struggling through a 2015 with a bunch of "He's the ace" t-shirts, and not much else, the Red Sox were forced to allocate $217 million to Lester's ultimate replacement, David Price. And when Price wasn't quite enough, they then got another guy, Chris Sale, to fill out the top of the rotation. That's a lot of money, a valued trade chip (Yoenis Cespedes) and two of baseball's top two prospects (Yoan Moncada, Michael Kopech) to figure out how to fix what seemed like an pretty easy fix. (In fairness, the Red Sox should have gone after Sale even if Lester was in the fold.)

And we aren't even talking about the lesson learned when it came to appreciating how much better Lester could manage the Boston landscape than his replacement.

As for Lester, he has pitched in 11 postseason games, totaling a 2.53 ERA, winning a World Series along the way. In total, the 33-year-old has gone 46-28 with a 3.26 ERA in his time with the Cubs, appearing in 107 games. 

What's done is done, three years after Lester officially became a Cub, the pitcher should represent one of the Red Sox' greatest missteps. If they really wanted him, they could have gotten him. That's a fact. And they've been paying the price (figuratively and literally) ever since.

Perhaps the four-year anniversary will present a slightly different narrative. But I wouldn't count on it.

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