Theo Epstein’s legacy as Cubs’ president puts him in the pantheon of Chicago sports executiveson November 17, 2020 at 10:39 pm

There’s no doubt that Theo Epstein is one of the greatest executives the game of baseball has ever seen. The future Hall of Famer has won three World Series titles before the age of 50 and broke two of the longest championship droughts in the history of sports.

Epstein stepping down as Cubs’ president on Tuesday closes a successful chapter in franchise history, but the legacy that he leaves behind with the Cubs and the city of Chicago will never be forgotten.

When Epstein came to Chicago in 2011, he had a plan and that plan was a difficult one. Take the Chicago Cubs from one of the worst franchises in sports and turn them into not only a contender, but one of the premier organizations in the game.

“Well, little over nine years ago, we went looking for a new person to lead our baseball department,” Cubs chairman Tom Ricketts said. “And we knew it would be a tall order. Not only did we need someone who could bring in some good players, and win some big games and maybe win a division, but we really needed someone who could change the culture and change the direction the organization had been going for a long, long time.”

Once hired, Epstein quickly won over the fanbase. Not with fancy signings and blockbuster trades that would come down the line, but he did something that fans in Chicago had rarely seen — honesty and transparency.

There was no hiding or running from criticism from the fans or the media. Epstein and Jed Hoyer, who will be named the new president of baseball operations, were upfront about the challenging road ahead.

“I think we rebuilt back then because we had to,” Epstein said. “It was more than just our strategy with what we did on the field. We had to build the organization up, the infrastructure, the personnel, the systems that we needed to put into place. And it coincided with a period where we obviously prioritized the long term over the short term, with the team on the field.

“I think what we did was right for us.”

That honesty and transparency didn’t go for naught as the on-field product began to match what Epstein’s vision was. That vision over the next nine years turned into five postseason appearances, three trips to the National League Championship Series and a 2016 World Series title.

Epstein’s legacy has written itself after breaking the Cubs’ 108-year drought. He oversaw the change from Lovable Losers to World Series champions — something that many never got to see in their lifetime.

But what he did as president changed the approach of executives in Chicago. Before the Cubs went through their complete overhaul, telling a Chicago fanbase that the road to sustained success would not be easy and that there would be tough moments would have been met with disdain and scrutiny.

But since the Cubs’ transformation, several teams in Chicago have also undergone their own attempts at rebuilds and have had similar discussions with their fans about the process. While their success still remains to be seen for those teams, it’s hard to imagine that change ever happening without the success Epstein and the Cubs had.

Epstein should be proud of what he built. The Cubs are now a model organization in baseball, something they weren’t when he first got to Chicago.

He also leaves a lasting legacy as an executive in Chicago and his style and ability as a communicator has changed the way people view front offices in this city and Chicago sports are better because of it.

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