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Alex Speier | On baseball

Theo Epstein challenges himself by walking away from baseball

Now that he has left the Cubs, Theo Epstein looks forward to "being able to sit with friends, unfettered, have a cold one, and enjoy the game.”stan grossfeld

Theo Epstein isn’t ready to write a book.

His baseball career isn’t over. His exploration of interests inside and outside of baseball isn’t complete. There are more chapters for the 46-year-old to experience.

“That’s for old people,” said Epstein.

Epstein isn’t old, but he is established and respected in ways that have allowed him to dictate his career path, rather than being told when it’s time to leave. That pattern repeated itself Tuesday.

Epstein and the Chicago Cubs announced that after nine years as president of baseball operations, and with one year left on his contract, he would step down to let longtime top lieutenant Jed Hoyer take over as Chicago enters a transitional period of reshaping the core that secured five playoff appearances and one memorable title over the past six years. The decision echoed one that he made to leave the Red Sox in 2011 to head to Chicago, only this time, Epstein expects to take time away from work for an individual team in order to spend time with his family and explore other interests.

“After a while, I need a new challenge,” Epstein said. “If you look at my track record in Boston and here, in the first six years or so, we did some pretty epic things, then the last couple years weren’t as impressive. Maybe what that tells me is that I’m great at and really enjoy building, transformation, and triumphing.


"Maybe I’m not as good and not as motivated by maintenance. As soon as you get to the point that it can start to feel that way to you, I think you owe it to yourself and, as importantly, if not more importantly, to your employer to be open about that and seek to pursue change.”

It is a testament to Epstein’s place in the game — and how he’s helped to reshape baseball — that his announcement commanded the attention of the entire sport.


Eighteen years ago, when a 28-year-old Epstein was introduced as the Red Sox general manager, such attention would have seemed misplaced save for the fascination with his relative youth. Now, however, he leaves the Chicago front office as one of the most established and significant figures in the sport, someone who will feature prominently in any examination of the sport’s history during the first 20 years of the 21st century.

“He’s a lock for Cooperstown, not just because of his historic accomplishments, but because of how he’s achieved them,” said Red Sox CEO/president Sam Kennedy, a Brookline High classmate of Epstein’s. “Everywhere Theo has been in baseball — Baltimore, San Diego, Boston, and Chicago — he created a culture of curiosity, collaboration, intensity, empathy, and more importantly, good humor. When you are on Theo’s team, you know you are going to win and have a hell of a good time along the way.”

Epstein has overseen the construction of three championship teams — two in Boston, one in Chicago — while in the process ending the two most famous title droughts in North American sports. The 2004 title that ended 86 years of Red Sox and the 2016 World Series triumph that concluded the 108-year run of losing by the Cubs secured his place in history.

“I think Theo Epstein earned his plaque in the Hall of Fame in 2016, by ending baseball’s second great World Series drought,” MLB official historian John Thorn wrote in an e-mail. “Whatever he may do henceforth, in baseball or out, his position in the game’s history and legend is unique.”


Yet Epstein wasn’t merely the architect of those title teams. He — along with Billy Beane of the A’s, the person whose decision to turn down the Red Sox GM job in 2002 launched Epstein into that position — was the face of something larger in the sport, the transfer of prominence from players to executives and the rise of the front-office superstar.

He graced the cover of the Globe Magazine in 2004 with the proclamation, “In Theo We Trust.” His first season as Cubs president of baseball operations was introduced by a full-page back cover in the Chicago Sun-Times that featured him walking on water.

Such attention made Epstein squirm at times, both because of the way it exaggerated his role relative to those of his front office colleagues and because of what it symbolized. Indeed, as he discussed his departure from the Cubs, Epstein discussed his desire to be involved in improving the game, to help to undo some of what he’d set in motion.

Epstein has assembled some of the most dynamic, character-filled clubhouses in recent memory — particularly those of the 2003-04 Red Sox and 2015-16 Cubs. But he’s also played a role in the clinical idea of “optimizing player performance,” a phenomenon that has drained personality from the game and made the extraordinary abilities of players at times seem confusingly interchangeable. And he also winced at the notion that his gut-and-renovate success with the Cubs helped popularize rebuilding —and the acceptance by too many teams of non-competitiveness.


“It is the greatest game in the world, but there are some threats to it just because of the way the game is evolving. I take some responsibility for that,” said Epstein. "Executives like me who have spent a lot of time using analytics and other measures to try to optimize individual and team performance have unwittingly had a negative impact on the aesthetic value of the game and the entertainment value of the game in some respects.

“Clearly, the strikeout rate is a little bit out of control. We need to find a way to get more action in the game, get the ball in play a little more often, allow players to show their athleticism some more, give the fans more of what they want. Maybe there’s a way to do that through changes over time to put the game back in the hands of the players and let them do their thing on the field . . . When you’re with a club, you don’t necessarily have the ability to be objective and contribute to that discourse. Maybe now that I won’t be with a club anymore, I can find a way to do that in some fashion.”

Despite speculation through the years of a potential dalliance in politics, Epstein suggested that he has no interest in the field — even as he is interested in the question of policies that can make a difference at the community level. Down the road, he expressed interest in being part of an ownership group of a major league team as one possibility for his anticipated next chapter in baseball.


In the meantime, his ambitions are more measured after spending the last 29 years working in baseball.

“I’ll look forward to that most of all — being able to sit with friends, unfettered, have a cold one, and enjoy the game,” said Epstein.

Whenever he does so, it will be part of an intermission — but not a final act in the game.

Alex Speier can be reached at Follow him @alexspeier.