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What Theo Epstein Could Mean To Chicago Business


We all know what franchise I’m talking about… or do we?

  • They play in one of the best “sports towns” in America.
  • Their fans are among the most passionate and loyal in all of sports, despite enduring decades of frustration and misery.
  • The ballpark they play in is the smallest in the league, and also the oldest and most-charming, with a legendary outfield wall.
  • For decades, the team was owned by one of the wealthiest men in sports, well-known for being a true “baseball man” and always paying his players top-dollar.
  • A famous “curse” haunted the franchise for generations.
  • The team had a long-time reputation for “choking” and failing to win a championship, even with large, seemingly-insurmountable leads and with rosters filled with All-Star talent.

After graduating high school, I lived for the next 17 years of my life in and around Boston, Massachusetts, before moving away for a business opportunity.

So when I arrived here in Chicago a little over a decade ago, “it was déjà vu all over again” (to quote baseball immortal Yogi Berra). I thought I had left everything I described above – but all I had really done was switch zip codes, because everything in the bulleted list above could be used to describe the Boston Red Sox from 1918 to 2004 as well as the Cubs from 1908 up to now.

Two of the largest cities in America, two beloved, historic baseball franchises, same star-crossed history.

Yes, I had moved halfway across the country, but as far as baseball was concerned, I had found myself in the same all-too-familiar (and all-too-depressing) situation.

Then yesterday, the Cubs made it official that someone else is making the same move from Boston to Chicago, announcing that Theo Epstein has become their new “President of Baseball Operations.” Similar to the way that my personal move has resulted in hundreds of Chicagoland business success stories, Epstein’s move could very possibly result in a complete turnaround of one very important business – the Cubs – if he is able to work the same magic he used to lead the Red Sox out of their decades-long darkness when he was baseball’s youngest General Manager just seven years ago.

During Epstein’s introductory press conference yesterday at Wrigley Field, he outlined a recipe for turning any struggling business into a success. Among the promises Epstein made were:

  • “To establish a winning culture”
  • “To work as hard as possible”
  • To bring in employees who care more about each other and about the success of the business; who have the right mindset
  • To build the best business of its kind
  • “To make building a foundation for sustained success a priority”

Finally, he vowed, “We’re going to have to grind our way to the top.”


I didn’t hear Epstein make any excuses about “the economy” or “the competition” or “oppressive regulations.” Yes, all those elements exist and make winning harder. But winners don’t let that stop us.

And my prediction is that Epstein doesn’t stop until he makes some major, fundamental changes in the way the Cubs are run, resulting in the franchise becoming known for excellence instead of futility.

Oh, there are bound to be the naysayers and doubters, just as whenever I take on clients and use some “out-of-the-box” strategies to lead them and their businesses to complete turnarounds and massive successes. But in the end, the results will speak for themselves.

And when they do, every small business owner would do well to model Epstein’s turnaround plan. Or, you could just get to work right away and not wait for the Cubs to win the World Series to start making the right moves in your own business.

(By the way: Each postseason baseball game brings an immediate boost of millions of dollars in additional revenue to the host city, in the form of money spent in the host ballpark as well as at area hotels, restaurants, etc., and the success of a sports team has been known to elevate the morale of the entire area and attract more residents and businesses to that city in the long-term. So even if you are not a Cubs fan, all Chicagoans should be rooting for the team’s – and Epstein’s – success. Go Cubbies!)

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