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