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Chicago Cubs: Theo Epstein’s five best moves as President

By Vincent Parise

Nov 2, 2016; Cleveland, OH, USA; Chicago Cubs president Theo Epstein holds the commissioner's trophy after game seven of the 2016 World Series against the Cleveland Indians at Progressive Field. Mandatory Credit: David J. Phillip/Pool Photo via USA TODAY Sports
Nov 2, 2016; Cleveland, OH, USA; Chicago Cubs president Theo Epstein holds the commissioner's trophy after game seven of the 2016 World Series against the Cleveland Indians at Progressive Field. Mandatory Credit: David J. Phillip/Pool Photo via USA TODAY Sports /
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Chicago Cubs Jon Lester
(Photo by Nuccio DiNuzzo/Getty Images) /

Jon Lester signing

The Chicago Cubs changed their franchise forever when they signed Jon Lester. It was Theo’s way of telling the world that the Cubs were done with the painful part of a rebuild and now trying to win. Well, Lester went on to become the greatest free agent signings in the history of the Cubs organization. Not only is he the greatest in Cubs history, he is one of the two best free agency signings in the history of the Chicago sports (Marian Hossa, Chicago Blackhawks).

Jon Lester came to the Cubs and was everything he was advertised as and then some. He brought that winning attitude to the team. Well, in his first year they made it all the way to the NLCS. They were swept  by the New York Mets  but it was clear that they were going to stick around for a while. Obviously, he became a three time World Series champion when the Cubs won it all the following year.

When you bring over a player like Lester, you bring over a certain attitude and a certain level of experience that you can’t find just anywhere. He delivered this team exactly what they needed in terms of performance and experience. They probably would not have had the same level of success that they did without Lester. It is clearly Theo’s crowning move.

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