Theo Epstein breaks down Cubs' challenges in quest for World Series repeat


Whether it’s building a perennial contender or defending a World Series title, Theo Epstein takes the same clear-eyed view of the situation. Whether it’s remodeling the Boston Red Sox or taking a sledgehammer to baseball operations at Wrigley Field, Epstein cuts through the clutter.

“The primary reason why it’s hard to repeat is just because it’s really difficult to win the World Series,” Epstein said. “In any given year, if you’re any old team, you have a 3-percent chance. If you’re the best team, you might have, you know, a 10- or 12-percent chance. So it’s just hard to do. But there are things that get in the way.”

If the rebuild didn’t obsess over curses, antiquated facilities, too many day games and Chicago’s nightlife temptations — or whatever other theories tried to explain the 108-year drought — then the next phase won’t be consumed with worrying about hangovers or players not being quite as hungry or motivated.

But Epstein’s three-dimensional worldview — his ability to blend scouting and analytics, his people skills balanced against a ruthless streak — won’t completely dismiss those concerns, either. The Cubs will experience their new normal on Tuesday, when pitchers and catchers officially report to Arizona, trying to become Major League Baseball’s first franchise to repeat since the New York Yankees won it all in 1998, 1999 and 2000.

“When you win, you get pulled in a lot of different directions,” Epstein said. “There can be a tendency — at some point, no matter how high the character — to start thinking about yourself a little bit more.

“You have to work really hard — we all do — to avoid any kind of organizational arrogance. (Or) any sense of entitlement to really understand that of all the great things that happened last year, the most special aspect is that we all got to be part of something bigger than ourselves.

“So it’s important to like opt back into that mindset, to buy back into being a team player, to being a team-centric organization.”

After a short offseason where they were celebrated in front of millions at the championship parade/Grant Park rally, on “Saturday Night Live,” all over the late-night talk shows, at Disney World and in the White House, the Cubs will go back to the grind next week. It begins with a camp lengthened by the World Baseball Classic, followed by 38 exhibitions, the 162-game marathon and what they hope will be three more playoff rounds.

“I don’t worry about our group,” Epstein said. “But with some teams after winning it, other things creep in and get in the way of that bonding.”

[SHOP CUBS: Get your Cubs gear right here]

These Cubs have clearly earned the benefit of the doubt so far, from the way they’ve handled the big-market spotlight and shrugged off the weight of franchise history. Instead of coasting, Kris Bryant followed up a Rookie of the Year campaign with an MVP season. After taking the security of a long-term deal, Anthony Rizzo matured into a team ambassador and an All-Star first baseman.

Addison Russell (23), Javier Baez (24), Kyle Schwarber (24 in March), Willson Contreras (25 in May) and Albert Almora Jr. (23 in April) should have so much of their careers in front of them and the carrot of a big contract. Jake Arrieta — who is positioned to become a free agent after this season — is pitching for his Boras Corp.-negotiated megadeal.

Maybe the rotation will finally break down and the Cubs won’t have five pitchers make at least 29 starts, the way they did last season, leading the majors with a 2.96 ERA. Maybe Wade Davis, Pedro Strop and Hector Rondon have trouble staying healthy and manager Joe Maddon gets roasted again for his bullpen decisions. Maybe the playoff matchups won’t be so favorable this year, either.

The San Francisco Giants reacted to their bullpen meltdowns by giving Mark Melancon a record contract (at the time) for a closer ($62 million over four years). The Los Angeles Dodgers didn’t really seem to trust anyone on their pitching staff beyond Clayton Kershaw, Rich Hill and Kenley Jansen. The Cleveland Indians made it to the 10th inning of a World Series Game 7 without Carlos Carrasco or a full-strength Danny Salazar.

Even if there are elements of luck and randomness, you still have to recognize the muscle memory and give credit to the mental toughness that it took to: eliminate a Giants franchise that has won three World Series titles since 2010; recover from back-to-back shutouts in the National League Championship Series; and storm back from a 3-1 deficit in the Fall Classic.

“We took another step forward,” Epstein said. “You gain an inner confidence, a default belief that you and your teammates know how to win. And through hard times, you just have a faith in getting back to what got you there, knowing that you’re good enough not only to compete, but to win and to win the whole thing.

“That kind of confidence is hard to create. That’s why you see teams kind of gradually do better and better and better the more times they’re in the postseason.”

Amid the raucous celebration at Progressive Field — at the beginning of his bender — Epstein compared being part of championships teams to having kids: “You cherish both of them. Different origins, different personalities, but they’re both things you treasure for your lifetime.”

After reversing the curse, the 2005 Red Sox got swept by Ozzie Guillen’s White Sox in the divisional round. The 2008 Red Sox lost an American League Championship Series Game 7 to Maddon’s upstart Tampa Bay Rays.

“Generally speaking,” Epstein said, “I think teams that win it all sometimes face unique challenges where a lot of things come up that pull everyone associated with the organization in different directions. So locking back into a team-first, competitive, connected mindset is really important.

“But that’s where having such great character guys is important. And I really trust our group to get locked back in again.”

Contact Us