Nick Cafardo | On Baseball

Theo Epstein’s only 44, but has seen so much

Theo Epstein, the Cubs’ president of baseball operations, hasn’t worked for the Red Sox since 2011.
Theo Epstein, the Cubs’ president of baseball operations, hasn’t worked for the Red Sox since 2011. Carlos Osorio/Associated press/file

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FORT MYERS, Fla. — Theo Epstein has been gone so long from Boston, the Cubs’ boss was making his first appearance at JetBlue Park. He left the Red Sox after the 2011 season; JetBlue opened in 2012. He’s become the Carlton Fisk of executives. Fisk started with Boston and ended in Chicago — the White Sox.

Epstein, now 44, used to be the young kid in the GM circles. Now he’s the highest-paid president of baseball operations — rumored to be earning $10 million per year.


“If you go back 15 years, it’s definitely changed a lot. I feel like the old guy now,” Epstein said Monday. “There are a lot of GMs that I don’t know that well. I rely on our younger guys to get in touch with them sometimes. I’m a dinosaur at 44. It’s a time of tremendous change in the game.”

He’s already won three championships, leading the Red Sox out of an 86-year-year old championship drought and the Cubs out of a 108-year drought. Those feats alone with get Epstein to Cooperstown one of these years.

In 2017, after the Cubs won the World Series, Fortune magazine named him the world’s greatest leader.

In the meantime, Epstein is trying to get the Cubs back into the World Series. Epstein knows all about the year-after hangover that so many teams, including his old Red Sox teams, suffered from.

“We tried everything we could to bounce back and repeat,” Epstein said. “We didn’t deal with it very well the first half of last year. The good thing is we woke up and we played great ball the second half. We had to expend so much energy the second half that we were pretty much fried in October. I admire any team in any sport who can repeat.”


He’s not surprised the Red Sox tabbed Alex Cora, a player he brought to Boston in 2005, to be the manager. Epstein could always identify the players who were managerial material and Cora was high on his list. The admiration society is mutual as Cora basically said before Monday’s exhibition game, “I want to be like Theo.”

What he was trying to say was he wants to come off as an unassuming, informal guy who’s great at what he does, but he doesn’t let you know it. He wants to remain humble like Epstein, be self-deprecating, and enjoy the game.

He said if it wasn’t for Epstein bringing him here to be part of a World Series team, “I might not be where I am today.”

“[Cora’s] just great feel for people and for the game,” Epstein said. “It’s genuine. He’s a genuine sort of non-stop curiosity about the game of baseball. Conviction in his opinions, but he’s open-minded. If he respects somebody, he’s willing to talk baseball and grow. And then his feel for people, as I said, he’s very convicted and can even be stubborn at times, but it doesn’t come off that way because he treats everyone so well and just has a natural sense of how to treat people and interact and empower the other person.”

Despite the analytic slant Epstein brought to the Red Sox (remember his system known as Carmine?), he has learned the numbers don’t mean everything. He has come to find that the enormous amount of data available is available to every team, so he thinks the data has to be used creatively and that the game comes down to human beings executing the data.


Which is why Epstein is still big on scouting, which has become de-emphasized in many of the overanalytical organizations. Epstein always employs a healthy mix of scouting and analytics, and he still values the decades of experience scouts bring. He thinks that experience is invaluable to the game and decision-making.

“All organizations basically have the same data streams and numbers, so it’s pulling you in different directions,” he said. “For one you have to look that much deeper to find that proprietary source of information or data that another team doesn’t have. You have to get really creative either through scouting or that double-secret confidential information that doesn’t become available to anyone else for a couple of years.

“You also have to develop really smooth forms of communication from the front office to the field. Since everyone has advanced data, it’s really important to find the right people to implement what you’re trying to do, from getting your manager involved, coaches involved, and ultimately the players.

“And the last issue is to go beyond the numbers and remember the game is played by human beings. So, if everyone has the same information, you really want to put a premium on a humanistic approach an understanding of the people and being able to support them as human beings and the chemistry of the group overall.”


Epstein keeps track of the Red Sox. Team president Sam Kennedy grew up with him in Brookline and they remain best friends. Bronson Arroyo, whom he traded for Wily Mo Pena in 2006. was at JetBlue on Monday as part of Epstein’s Cool Music party.

He keeps track of players that were drafted while he was in charge. Mookie Betts, for one.

“I didn’t anticipate Mookie being second in the MVP voting and one of the best players in the game, but he’s gotten the most out of his ability,” Epstein said.

He’s now firmly entrenched in Chicago, where he expects to be for a long time. Epstein always though that every career should have a 10-year shelf life and everyone is anticipating what’s next for him.

If he ran for senator in Illinois, as some people think he may, many people think he would win. The interesting dynamic is that Epstein is a diehard Democrat while his boss, Cubs owner Tom Ricketts, is a Donald Trump supporter.

Somehow politics has never stood between them.

He says working for the Cubs “is a fun place to come to work every day. It’s now a destination. We feel privileged to be here. We don’t get everything right, but we all get along. A rewarding, fulfilling environment.”

While Epstein would love another shot at a World Series, part of him wants it to be against the Sox. He thought it might happen each of the last two years, and he knows the possibility exists as long as the “window” he speaks of is open for both teams.


“Time flies,” Epstein said. “Things move on without ya. Happy to say it worked out well for everybody. Both franchises are in a good place. Everybody is excited about the young nucleus in place in Boston. They are one of the best teams in the American League. We have one title and we’re in the middle of a competitive window.”

As the architect of two storied franchises, Epstein has conquered the baseball world and wants more.

Nick Cafardo can be reached at cafardo@globe.com. Follow him on Twitter @nickcafardo.