Chicago Cubs: Theo Epstein’s five best moves as Presidenton November 19, 2020 at 12:00 pm

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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 Theo Epstein

Mandatory Credit: Patrick Gorski-USA TODAY Sports

The Chicago Cubs have had a lot of success recently and Theo Epstein deserves a lot of credit.

The Chicago Cubs have been one of the most successful franchises in all of baseball since Theo Epstein took over as the President of Baseball Operations. He came in after ending “The Curse of the Bambino” with the Boston Red Sox. He wanted to take on a new challenge and there weren’t many bigger than trying to end the century-long World Series drought that the Chicago Cubs were in. He did a great job with that challenge as he turned the Cubs into a dominant team for half a decade.

The peak of the dominance came in 2016 when the Cubs ended their drought at 108 years, winning the World Series for the first time since 1908. A lot of people went into that accomplishment but none of them even come to close Theo Epstein in terms of importance. He is the most important person to ever collect a paycheck from the Chicago Cubs in the history of their franchise.

The Cubs, even if they rebuild, now have a certain reputation to keep. Theo turned them into a team that will always have respect like the New York Yankees, Los Angeles Dodgers, or Boston Red Sox. They might not be that good for a while but they will always be respected.

Of course, there has been a few mistakes. Some of the trades and free agency signings have gone south (no pun intended), especially recently, but that is usually the case for everyone. Most of the moves that led to them being a championship team in 2016 were at the hands of Theo. These are the five best moves he made as Cubs President:

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