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Domopalooza 2017: What Drives the W for the Chicago Cubs

Salt Lake City—Cubs win.

Has there been any greater reversal of fortune in modern sports? The Chicago Cubs, once widely known as baseball’s loveable losers, are again World Series champions after a brief, practically unnoticeable 108-year drought. Cubs fans the world over have been letting their W flags fly.

But what drives the W?

That’s a question only one man could answer—a man whose leadership helped break not only the Cubs’ championship-less curse, but also the Curse of the Bambino, a slightly-shorter championship drought that plagued the Boston Red Sox for 86 years—President of Baseball Operations for the Chicago Cubs, Theo Epstein, who spoke this afternoon as part of Domopalooza 2017.

Of course, the answer everyone wants to hear is some kind of numbers-and-analytics-driven Moneyball scenario that they can then take into their own business and make work for them. And while baseball analytics were an invaluable part of the process that helped build the World Series-bound teams of the Red Sox and Cubs, that’s certainly not the whole story—but the lessons Epstein has learned from his experiences both simpler and far more complex than that. Epstein builds his teams off a fundamental understanding that there is merit to both numbers and gut instinct, the old school and the new school, that help drive results.

“Empathy is a big part of building any successful organization,” he said.

Fifteen years ago, Moneyball hit Major League Baseball like a ton of bricks. Joking that rich old MLB owners “always read the New York Times Bestseller List,” Epstein said what was then only five teams using baseball analytics ballooned to include the entire MLB team roster. Epstein, who worked for one of the few teams using baseball analytics before the massive swap, serendipitously had his cubicle between the team’s scouting director (who never wanted to look at a single statistic, but only wanted to watch players play) and the team’s analytics director (who never wanted to see a single player play).

“Those two hated each other,” Epstein laughed. “That’s where my own personal philosophy really emerged, because I saw that there was tons of merit to both of their arguments, but they got really dogmatic and really critical of the other perspective… When you look through both lenses and you still have a clear picture of a player, that’s where you want to place your bets. I’ve tried to build the organizations I’ve been with around that model—but it takes a lot of empathy. I found the best tool is getting both sides talking and helping to push each other.”

Relying on the Moneyball approach of finding metrics that others have overlooked was helpful in the early days of baseball analytics, said Epstein, but as the landscape began to “flatten,” common baseball data and analytics interpretation became easily available. The insights that helped Epstein and the Red Sox front office practically steal first baseman David Ortiz—who would go on to become a 10-time MLB All-Star and World Series MVP—quickly became commonplace.

“You have to ask the questions nobody is asking” to get a leg up on the competition these days, says Epstein. To that end, the Cubs have begun delving into the field of neuro-evaluation and the science behind what a Major League Baseball hitter’s brain looks like—while still utilizing area scouts to get to know the prospect’s talent, yes, but also character, habits, personality, leadership skills and other intangibles.

“The flat [analytics] landscape now has left room for three different areas where you can find competitive advantages. One is going deep and finding something that nobody else does … The second is to try to be better than your competitors at getting that information and getting it onto the field. Every organization has a team full of analysts sitting in a boiler room crunching numbers, analyzing the information, but it doesn’t do any good unless you can get it onto the field,” said Epstein, who added that it’s hard to convince a player to move from a position they’ve spent their whole life at because “a spreadsheet told them to.” Bolstering communication by using smart ex-players to bridge the gap between player and analyst has been deeply helpful, he said.

“The third area you can still get competitive advantages, and this one is pretty ironic, is by remembering that the game is played by humans,” Epstein continued. “The analytical landscape is so flat and advanced that you really have to drill really deep and be selective in where you can find advantages—but it’s swung the pendulum back that too many decisions now are driven exclusively by data. You don’t remember that [you’re talking about] a real live person who is complicated.”

It may seem intuitive, but Epstein said it took four days of constant meetings and the writing of a 350-page manual to make sure everyone in the Cubs organization understood how he meant to lead the organization. And those precepts—empathy, communication, constant evaluation of internal processes and innovation—only helped Epstein break a combined 194 years of baseball curses.