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Theo Epstein’s legacy as Cubs’ president puts him in the pantheon of Chicago sports executives

When Epstein got to Chicago in 2011, he was transparent about what the organization would have to do to return to relevance. That transparency helped him stand out as an executive.

The Cubs were Lovable Losers when Theo Epstein arrived. He leaves with a World Series ring and hands over a perennial playoff team.
The Cubs were Lovable Losers when Theo Epstein arrived. He leaves with a World Series ring and hands over a perennial playoff team.
Ashlee Rezin/Sun-Times

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

Epstein’s decision to step down as the Cubs’ president of baseball operations Tuesday closes a successful chapter in franchise history, but the legacy he leaves behind with the team and the city of Chicago never will be forgotten.

When Epstein came to Chicago in October 2011, he had a plan to transform the Cubs from one of the worst franchises in sports to one of the premier organizations in the game.

‘‘Well, a 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 fan base. He didn’t do it with fancy signings and trades, which would come down the line, but with something fans in Chicago rarely had 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 promoted from general manager to president of baseball operations, were upfront about the challenging road that lay 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 when the on-field product began to match Epstein’s vision. That vision 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 since he broke the Cubs’ 108-year title drought. He oversaw their change from lovable losers to World Series champions, something many never got to see in their lifetime.

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

But since the Cubs’ transformation, the Bears, Bulls, White Sox and Blackhawks have all 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 that couldn’t be said of them when he came to town.

Plus, his leadership style and ability as a communicator have changed the way people view front offices in this city, and Chicago sports are better because of it.