BOSTON — It’s a different Theo Epstein who returns to Fenway Park on Friday with the Cubs for the first time since a contentious departure as general manager of his hometown Red Sox in the fall of 2011.
He’s five years older and grayer, certainly. Five years wiser, perhaps. But most conspicuously these days, he’s lugging around the largest, most valuable piece of championship jewelry ever made for a baseball team.
“I think I’ve definitely grown up a lot — at least I hope I have,” Epstein, 43, said as he arrived in Boston for a weekend series that promises to be a media circus under the bright lights of national broadcasts Saturday and Sunday. “I think I’m better at picking my battles, compromising and seeing the big picture. I feel like I’m still just as committed to the things I feel are important — in the organization and in life — but maybe I’m not quite as much of an absolutist.”
Whether or not that helped lead to the right pieces coming together as quickly as they have for the Cubs, Epstein’s newest World Series ring is his third in 14 years of running baseball operations for two of the most storied franchises in the sport. The two from the Red Sox are from the Bambino curse-buster in 2004 and from 2007.
“What separates him is his ability to build for the long haul,” said Cubs pitcher Jon Lester, a key to the 2007 title who was drafted by the Red Sox a year before Epstein was promoted to general manager. “To be able to sustain it, that’s where I think he puts himself above and beyond a lot of execs. If he’s not the top [all-time], I would say top three.
“I mean, you orchestrate three championships for two pretty historic organizations that have a lot of [crappy] history as far as winning, I think that puts him up in the top.”
Epstein didn’t make the trip the last time the Cubs played in Boston, in 2014, when his wife was due with their second son. This is his first public return since the 2011 Red Sox collapse that led to organizational upheaval, fan backlash and — after years of butting heads with his boss and mentor, Larry Lucchino — Epstein’s departure with a year left on his contract.
It was actually his second parting with the Sox. He reconciled a few months after his famous Halloween exit from Fenway in 2005, wearing a gorilla suit to avoid reporters.
“In an ideal world, we would have continued playing great ball through September and October of 2011 and I could’ve wrapped up my Red Sox decade with a neat, little bow,” he said. “But life doesn’t work that way, so the opposite happened.
“But it was time to move on, and sometimes you don’t get it to be completely the way you would want it to be. I am really proud of everything we all accomplished together in Boston and how the franchise changed during the decade we were there. As time moves on, you remember all the great times and not the handful of tough moments.”
“I have a very nasty habit of listening to too much sports radio in Boston, and so does my dad,” said Theo’s fraternal twin brother, Paul, in a conversation during the playoffs last fall. “Around the time that [Theo] was leaving, the memories got short, and it was the ‘What have you done for me lately?’ So that was a hurtful dynamic. But things are better now.”
Epstein maintains strong ties with many in the Red Sox organization, including regular contact with close friend and team president Sam Kennedy — if not so much Lucchino (who has since moved to a position with the Red Sox’ ownership group). Epstein said Red Sox chairman Tom Werner has reached out more than once since the Cubs’ World Series victory, and he feels a “real connection” with the Sox.
His fingerprints remain. Several Red Sox stars acquired under him as amateurs are still there, including Dustin Pedroia, Xander Bogaerts and Mookie Betts.
“I’m proudest, I guess, that the championships in both places were true organization-wide efforts that featured a lot of teamwork,” Epstein said, “and many genuine connections that will last a lifetime.”
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