Alec Messino 

 
Theo Epstein and The 2016 World Champion Cubs 
 
When most people think of Theo Epstein and his seemingly feasible ability to piece 
together dynasty-destined teams, they imagine a group of Paul DePodesta-esque quants, 
crowding around a conference table lined with supercomputers. They sit there -- 
crunching numbers, running through data analysis, scanning over performance charts. 
Though he is a Yale Alumnus, Theo Epstein is not ​just​ a quantitative genius. 
 
As Chicagoans celebrate their long-awaited and well-deserved World Series 
Championship today, an interesting story comes to the forefront. How did the team’s 
architect, Theo Epstein, take a “lovable losers” franchise that had just recently lost a 
hundred games in a season and turn it into the title-winning juggernaut it’s become? 

As the New York Times relays, studying the qualitative attributes of the players 
themselves was just as important as looking at the numbers. Theo Epstein, Jed Hoyer, 
and the rest of the Cubs home office are interested in things like how the players 
responded to failure and other “soft skills” that don’t necessarily show up in a 
quantitative screen. Needless to say, this is a fascinating subject for managers– especially 
given the data-driven approach that now embodies the zeitgeist of the sport’s 
management industry. 
 
In an ​interview​ with the New York Times, team president Theo Epstein said he 
specifically wants to know how players handle failure. Even the best hitters fail seven 
out of 10 times, and the most successful teams may lose 60 games a year.​ “In the draft 
room, we will always spend more than half the time talking about the person rather than 
the player. What are their backgrounds, their psyches, their habits, and what makes them 
tick?” ​says Epstein. 
 
Unlike the grizzled scouts of Moneyball, Epstein doesn’t rely on vague impressions. 
Investigations into character have become systematized. For players the Cubs may want, 
Epstein asks his scouts to produce three detailed examples of how players faced 
adversity on the field, and three examples off the field. Far from merely making 
touchy-feely decisions based on gut instincts, however, Epstein was able to systematize 
the way he looked at players’ soft skills into an evidence-based process.  
 
Chicago Cubs Manager, Joe Maddon, reiterates: ​“He really does listen to the human side of 
all this — it’s not just numbers, by any means,” -- “He gets it that there’s a balance between 
the sabermetric world and the real world. These are human beings and not computers.” 

In the book the movie was based on, author Michael Lewis and his subject, Oakland 
A’s general manager Billy Beane, scoffed at the idea that anything other than 
results should matter in player evaluation. The A’s were relentlessly analytic, and 
any player attribute that couldn’t be measured had little value. That approach gave 
the tightwad A’s a market advantage which they exploited. 

The gospel of Moneyball spread throughout baseball during the last decade, and 
now virtually every team crunches player data to find a statistical edge. Thus, the 
Chicago Cubs have pivoted again, and built the best team in baseball by screening 
for those easily mocked qualities like character and personality. 

"The only thing I know for sure," T​ heo Epstein once said​, "is that whatever team wins the 
World Series, their particular style of play will be completely en vogue and trumpeted from 
the rooftops by the media all offseason -- and in front offices -- as the way to win." 
 
That is absolutely true. This was true before this incredible Cubs season, before the 
playoffs started, and long before the Chicago Cubs won the World Series this year. The 
whole league is changing. The New York Yankees aren’t able to buy championships, and 
the players that produce them, any longer. Players are landing outrageous contracts for 
longer terms than seen before (Heyward, Stanton, etc), limiting the ability to secure 
players at their peak. Talent is now harvested from within, making scouting and the 
growth of farm systems more important than ever. 
 
The Cubs’ championship bookending the Red Sox championship 12 years ago suggests we 
are approaching the end of an era in baseball: a recognition that a front office that melds 
analytics and scouting information, that sees no contradiction or controversy in using 
data of all types to inform its decisions, is the inevitable harmonic perfection of what a 
major league front office should look like, and that every organization in baseball is 
heading in that direction. It doesn’t mean the game will be less interesting; on the 
contrary, the competitive urge to find an edge over rivals will spur more innovation 
(defensive shifts! pitch framing!) over time, introduce previously discarded strategies 
(use your best reliever to put out a crisis in the middle innings!), and create a game of 
strategizing cat-and-mouse off the field that’s nearly as compelling as the game on the 
field. 

If you’re a Cubs fan, it’s time to party like you’ve never partied before. You deserve it. 
But if you’re a baseball fan, and a fan of smart front offices doing incredibly smart 
things, pushing the envelope, trying new strategies in a never-ending quest to secure a 
competitive advantage, you should be rejoicing, too. A deeper understanding of the game 
of baseball not only makes for a better front office, but for a better fan experience. Cubs 
fans, and Red Sox fans before them, may owe Epstein a particular debt of gratitude, but 
we’re all indebted to him for helping make the game of baseball more rewarding to 
follow in 2016 than it’s ever been before.