Theo Epstein has no interest in running another major-league team — for now

CHICAGO — Amid a wave of nostalgia for the Chicago Cubs team that ended a 108-year championship drought, former club president Theo Epstein reaffirmed his desire to avoid the day-to-day grind of running another major-league franchise. At least for now.

Epstein currently holds a minority ownership stake in the Boston Red Sox and serves as a senior advisor to Fenway Sports Group. A masterful storyteller, his ability to communicate and connect with all types of people helped him become one of the most famous and accomplished executives in professional sports history.

Returning to Wrigley Field for Saturday’s 10-year reunion of the 2016 World Series team, Epstein reflected on the sense of purpose and pressure felt by a group that he largely handpicked.

Recurring images popped into his head as he worked tirelessly to transform the Cubs from “lovable losers” into the greatest show in baseball, adding another dimension to a Hall of Fame-caliber career.

“Along the way, up until November 2016, I would wake up from time to time with this dream,” Epstein recalled, “an awesome dream that we won the World Series with the Cubs and we were getting ready to go to the parade and everything. And then I’d wake up and be like, ‘Oh s—, we’re still building this thing.’

“It was such a letdown every morning when reality took over,” Epstein continued. “And then the morning when we got back from Cleveland, we all took a nap. I woke up again with that same feeling, like, ‘Oh, yeah, we did it! Oh s—, wait, was this a dream? No, this is real!’ That’s when it sunk in for me. It just felt like liberation.”

That newfound freedom is what Epstein continues to cherish.

“This is nice,” he said in the Wrigley Field plaza after a dedication ceremony for the new “Champions Gate” commemorating the franchise’s three World Series titles over 150 years. “But I love my life right now, too.”

Epstein’s instincts and gravitas helped unleash the Cubs as a multibillion-dollar franchise at a time when the Ricketts family ownership group was preserving and modernizing the Friendly Confines. Hiring Epstein as president of baseball operations after the 2011 season led to sweeping changes.

Feeling some burnout at Fenway Park, where he ended an 86-year championship drought by artfully adding pieces to what eventually became Boston’s 2004 World Series team, Epstein saw the Cubs as his next great challenge.

Piece by piece, his group traded for Anthony Rizzo, Jake Arrieta and Kyle Hendricks; drafted Kris Bryant and Kyle Schwarber; signed free agents Jon Lester, Ben Zobrist and Dexter Fowler; and hired Joe Maddon, the perfect manager for that moment.

“Nothing ever goes perfectly according to plan,” Epstein said. “There were plenty of missteps and errors and misjudgments by me along the way. But for the most part, one of the perspectives that 10 years gives you is that it’s really hard to win.

“It’s one thing to assemble a bunch of talent. It’s another thing to have that group turn into a championship team that stands up in the face of adversity at the most important times. That’s more than just numbers. That’s more than just talent. It’s what these guys are about, and how they come together as a group.

“If you remove any one of those people from the mix, it’s different and we don’t win. Obviously, all the players, but even people behind the scenes, everybody contributed in their own way and sacrificed together. So, yeah, you can’t plan for that, but you can bring in the people with the right stuff, treat them the right way and try to nurture it.”

Listening to Epstein talk about culture and team-building, it’s natural to wonder if he would want to become more heavily involved in the sport at the club level again rather than his previous consulting work with Major League Baseball.

Whatever else is out there, it probably doesn’t involve frequent text messages from beat reporters, nonstop calls from doctors and trainers with injury updates, and everything else that comes with a 24/7 job and no true offseason.

Seeking to better align his personal and professional responsibilities, Epstein resigned after the pandemic-shortened 2020 season and relocated to Connecticut to be closer to extended family on the East Coast.

“I’ve got plans,” Epstein said. “But for where I am right now, I’ve got a perfect balance. I have a very fulfilling mix of professional roles, and I also have an amazing family. I’m getting to spend time with them. My oldest is getting ready to go off to college, so I’m right where I want to be.”

By walking away with a year remaining on his contract, Epstein also helped orchestrate a succession plan that allowed his longtime general manager, Jed Hoyer, to become team president and make the big decisions on the remaining members of the 2016 team.

When Epstein first arrived in Chicago, he attributed a guiding principle to legendary football coach Bill Walsh, who believed leaders have a shelf life that lasts about 10 years. By that point, Walsh believed, coaches and executives should embrace change or risk becoming stagnant.

But if the Cubs hadn’t won that epic Game 7 in Cleveland and 1908 still hung over the franchise?

“Well, I wouldn’t have left voluntarily,” Epstein said. “We were all here to do one thing. We got it accomplished. Everyone was in it together. Everyone can die happy. We had more work to do, but that’s when it sunk in for me, knowing that I could choose my path going forward. (But) I wasn’t going to leave without getting the job done.”