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Men’s Chicago Cubs Jon Lester Majestic White Home 2016 World Series Champions Team Logo Patch Player Jersey

In December of 2015, the Chicago Cubs made an organizational-changing acquisition, when they inked starting pitcher Jon Lester to a six-year deal, worth $155 million.

Since this signing, the Chicago Cubs have gone to heights never seen by anybody on earth, and heights that every organization aims to reach. In his three seasons with the Cubs, Jon Lester has made 96 starts, posting a 3.33 ERA, pitching 588 1/3 innings, striking out 584 hitters, and posting a 3.45 FIP, and that’s just the regular season.

In the postseason, Lester has made nine starts, his best being game one against the Giants in the NLDS and a do-or-die game five of the World Series against the Indians. The Cubs won the World Series in seven games, just in case anybody forgot.

Jon Lester could retire now, not pitch the last three or four years of his contract, and still be considered a legend in Cubs lore. Lester changed the culture instantly, as many people thought, even at the time of his signing, that the Cubs were still a year away.

They promptly won 97 games in 2015 and made their first of three straight National League Championship Series, a streak that’s still active. Lester has been the guy that has aided this turnaround. Well, he, and the loaded core of young hitters on offense certainly helps, too.
Projecting Lester in 2018

This is a weird case. Lester had an outstanding 2nd half of 2015, a dominant 2016 (like the entire rest of the team) before regressing a bit in 2017. The question that many fans may have is whether or not his 2017 season was a case of natural regression, or whether it was his age getting to him a little? Lester will be 34 in 2018, so you could naturally assume regression will come. But, over the course of his career, Jon has been a bulldog, and will always take the ball when asked.
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His velocity during last year was fine, and the breaking ball was there. He just fell into the trap with the rest of the Cubs that involved a slight World Series hangover for the first half of the season. A betting man would probably bet on Lester to return to his normal self in 2018. But, this is baseball, and strange things happen every day.

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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