Confirmed: Theo Named World’s Greatest

Boston Red Sox fans knew this, Chicago Cubs fans learned this, and now Fortune Magazine has confirmed it – Theo Epstein is the world’s foremost leader. Theo took a solid roster in Boston, made some tweaks, and won a couple of World Series titles. He then famously moved on to Chicago, and the task wasn’t as simple.

The work that Theo has done in Chicago will certainly earn him the quick pass into baseball immortality, once he is eligible. But his story is far from over, and his Chicago story is far from being complete.

It wasn’t always easy

It all started in Chicago with many bumpy nights, too many box scores resulting in losses, and an incredibly tough ask of Cubs fans. Theo began his tenure in Chicago losing 286 games in a three-year span (2012-2014). With fans clamoring for the team to sign the likes of Albert Pujols and Prince Fielder, they would trade for a relatively unknown player in Anthony Rizzo. Cubs favorite, Ryan Dempster, was shipped out of Chicago for a light hitting third base prospect and a far off pitcher in Kyle Hendricks.

The identity on the field was changing as much as it was off the field. Fans were staying away from Wrigley at almost a record pace. Heck, I bought a four-pack on a June night for $12 total at one point during the 2012 season. Unlike many fans that year, we had something to talk about the next day – Cubs All-Star Bryan LaHair hitting a game-winning home run against the Cardinals.

Yes, I said All-Star Bryan LaHair.

Normally fans, media, and radio hosts would blast an organization in Chicago for being as horrible as they were. But that wasn’t the case. Even the toughest critic in Chicago media, WSCR’s Dan Berstein, fully backed the Cubs plan. When there was an ignorant caller, complaining about the Cubs, he would fire back and defend the process. The support was there, but it was never easy.

The support was there

Theo himself admits that the job he inherited in Chicago was a much more difficult task than anticipated. Early in his Chicago tenure, Theo was on a conference call with Cubs leadership. One of the members was late to the conference call, and in the midst of trying to fill out a roster (which would lose 100 games) Theo calls him out (paraphrasing), it’s okay, jump on when you like, we’re only trying to break a 100-year championship drought.

It was a funny moment, but in a sense serious. That was the enormity of the job he chose – break a 100-year curse.

This took a complete overhaul of the Cubs roster. Trading pieces that were old or expensive, and often times both. Allowing contracts to expire, trading fan favorites. And these were the parts Theo could predict. The Cubs most popular jersey had to of been a nameless one, as outside of Starlin Castro, there wasn’t a player you could hang your hat on.

What he was unable to predict was how far behind the Cubs organization was. From antiquated computer systems to scouting methods that were behind the times, the foundation of the organization needed fixing as much as the product. Theo ushered in that change.

Character

There were baseball changes as well. From the type of players, the organization would target, all the way down to building a singular mission statement. Theo changed the entire scope of the organization, leading them to a championship culture – something that was missing for the past 100 years. As Fortune mentions, he laid out a complete strategy before his first season in Chicago – how the Cubs will win the World Series.

A few weeks before spring training of 2012, in the ballroom of a budget hotel in Mesa, Ariz., Theo Epstein stood before nearly every person connected with the baseball operations of the Chicago Cubs and told them how the Cubs were going to win the World Series.

Epstein devoted the first three days of the session to on-field strategy: hitting philosophy, pitching philosophy, defense, and baserunning. But the entire last day was devoted to character. The Cubs, Epstein insisted, would acquire only players with outstanding makeup. Even Epstein realized himself how far he had evolved since he put so much faith in numbers when he began as general manager of the Red Sox. Now character did not just matter. It was essential to Epstein’s blueprint to win the World Series.

Looking at the Cubs roster now, a player’s character is the largest reason the organization has found success.

The front office’s character is unquestionably strong. Theo learned early on that honesty to players and agents was always the best policy. If they promised something to a player, it would happen. Look no further than Jason Hammell. The team had promised to him that they would release him, before burying him in a role which he wouldn’t be used much in. This would allow him to seek out his next stop, and earn his way onto a rotation which he would pitch 30-35 times a season. They honored this promise when they released him after the season ended.

Theo would ask for his scouts to provide extremely detailed and exhausting reports, not only on a players abilities and production but on their character. Reports on if they would help an elderly person cross the street. Details on how they react in ethically questioning situations. Noting if they’ve ever only done nine reps when they were supposed to do 10.

Modesty

Theo is quick to deflect the honor. Publically he is as modest as they come, and accepts the title of Worlds Greatest Leader, with self-depreciating humor. When asked, Theo told ESPN’s Buster Onley its “patently ridiculous” that he was named. He would further joke that he can’t even get his dog to stop peeing in the house.

This is what makes Theo successful. Through his modest efforts, he has created the greatest culture in sports today. His success, while it is his, is everyone else’s success in his eyes. This is one of the greatest attributes of a good leader. They may build the plan, put the people in their place, but they entrust those in the positions to do their job and be successful.

Modesty allows others around him to feel accomplished. It was the work of the people around Theo that were successful, and that is why he is a success.

There certainly is a lot more to the Theo story, and several more pages in the Cubs chapter of his life’s work. Here’s to hoping he earns a couple more rings while he’s here along the way.