How Theo Epstein has changed from Boston to Chicago
MLB 

MESA, Ariz. — His colleagues say he’s as competitive as ever, but there’s little doubt current Chicago Cubs president and former Boston Red Sox general manager Theo Epstein has changed over the years — but that’s mostly due to his situation in life. When he was running the Red Sox at the absurdly young age of 28, the middle-of-the-night “aggressive” email to a staffer wasn’t uncommon. These days, the emails still come, but mostly during working hours.

“At 3 a.m., when you have two young kids and have to get them off to school in the morning, you better be sleeping,” Epstein joked over the weekend. “In the past, at 3 a.m., maybe I was just coming in, and I would check email and send one off.”

Epstein’s worlds will collide over the next two days as the world champion Red Sox take on Epstein’s 2016 champion Cubs in exhibition contests as the final tune-ups for both teams before the regular season begins. The 45-year-old is likely to make the Hall of Fame someday due to his work with both organizations, winning three World Series rings in the process.

“He’s still just as competitive as ever,” longtime Epstein lieutenant and Cubs general manager Jed Hoyer said. “He’s still a baseball rat at his core. He still relates to all sorts of people exceptionally well and has an IQ and EQ [emotional quotient] that’s off the charts.”

Hoyer and other colleagues paint a picture of the Cubs being the beneficiary of Epstein’s decade run in Boston. Back then, he was simply the “smartest guy in the room,” but by the time he came to the Chicago, he could add a world of experience to his résumé. It has taken him to another level in terms of leadership.

“It’s been fun for me to see the difference in him from then until now, because in Boston, he was figuring it out,” Hoyer said. “Most people can’t figure it out on the job, in a big media market, and now in Chicago, he knows himself better. He knows how to be a leader, and he knows what he’s looking for in people around him.”

Asked if he has mellowed over the years, Epstein didn’t think that was the right word.

“Everyone is different at 45 than they are at 28,” he said. “Thankfully, I have more things in my life that are important to me now. Back then, it was helping the Red Sox win, and that took up almost all my time. Now, I have a great family at home that is precious to me. You have to be smarter how you work.

“We’ve structured things to allow ourselves to give everything we possibly can to the Cubs and still be happy at home. That’s important.”

Being more efficient came up several times in conversations about Epstein. Jason McLeod, the Cubs’ vice president of scouting and development who followed Epstein from Boston to Chicago, has been on the other end of some of those middle-of-the-night marching orders.

“Boston Theo was very hard-charging,” McLeod said. “You have to remember, this guy operates on a motor that is not normal. He doesn’t sleep much. He’s always on the go. He’s learned how to channel that more. A lot of it comes with being a husband and dad.

“He’s still driven as much as he ever was. He’s still as competitive as he ever was. With age comes more wisdom. He’s always been the smartest in the room, but in terms of managing people, relationships with players, he’s gained a maturity of sorts.”

Understanding and connecting with players might be the biggest difference in Chicago Theo compared to Boston Theo. Years of being around elite athletes can provide extra perspective, as Epstein has developed an appreciation for the human element more and more. Some find that surprising because of the Cubs’ reputation for being at the forefront of technology and innovation, but the human connection with players has always been an under-reported aspect of Epstein’s behavior.

“I understand better the ups and downs in a player’s career and the different factors that contribute to the arc of a career,” Epstein said.

Hoyer added: “He really values team-building now more than ever.”

McLeod has a theory on why that aspect of Epstein’s psyche has evolved.

“He was always the youngest guy in the room,” McLeod said. “That forces you to connect.”

According to players who know him best, there’s one trait of Epstein’s that hasn’t changed over the years.

“What’s great about him is he’s honest,” Cubs first baseman Anthony Rizzo said. “That’s pretty rare in this game, from what I know. … When I got traded [from Boston], he talked to me and said, ‘I’ll get you back one day.'”

Perhaps the most public of Epstein’s evolution as an executive is his ability to articulate — sometimes about the most sensitive of subjects. Whether it’s about a five-year rebuilding plan or walking the line in explaining why the team decided to keep a player — Addison Russell — suspended for domestic abuse, Epstein has arguably navigated the potential landmines as well as anyone.

“When I see him get up in front of the team or in a press conference, I see the confidence of someone that has done it and is comfortable in his own skin,” Hoyer said. “It resonates with people. They know he’s genuine.”

Hoyer isn’t wrong. It might not be scientific, but reaction before and after Epstein’s explanation for keeping Russell was night and day. If anyone can give such a rational and genuine take in the midst of such a sensitive topic as domestic abuse, it’s Epstein.

“There’s just a greater comfort level with greater experience,” Epstein said. “The more you’ve seen different situations, the more you can anticipate things that might come up, the more you understand interpersonal and organizational dynamics.”

In the end, his colleagues don’t see that a big of a difference in Epstein over the years — and neither does he. There might be a sore muscle or two more often after playing soccer with his colleagues, but his desire to win, to understand people and the game and the innovations that come with it, is no different than it ever was.

When the Red Sox and Cubs take the field Monday night in Mesa, Epstein can look out on the field at two organizations that have reached the pinnacle of success because of him. He might have grown as a person, but he has the same desire to come out on top — despite already accomplishing everything the game has to offer.

“I’ve seen the evolution of a person trying to figure it out to someone that has figured it out,” Hoyer said. “What he accomplished in Boston is startling, but I think he’s learned and grown on the job every year since. Both cities have benefited.”

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