Asked if the Cubs would have baseball’s best record without Epstein, Ricketts, whose family bought the team in 2009, responded, “Probably not.”
When listing the most pivotal steps in the Cubs’ resurrection, the first thing Ricketts mentioned was hiring Epstein, a move he made after every person he questioned in baseball put Epstein atop a wish list.
These are heady times for Epstein, whose dream job might actually be playing guitar for Pearl Jam, his favorite band. He has performed on stage with the band, whose frontman, Eddie Vedder, is a Cubs fan and considers Epstein a friend.
It is in keeping with an eclectic background that ultimately could steer him to other opportunities.
Epstein, who has a law degree, has ruminated about working for a philanthropic organization. He has turned down several million-dollar book offers. He has talked about being a consultant in baseball someday.
But for now, as the playoffs are about to begin and the Cubs phenomenon is the sport’s biggest national draw, it will be Epstein’s winning baseball tactics and methods that will be most highly scrutinized and discussed.
The Cubs’ achievements, he said, occurred in piecemeal, prudent steps — like taking a daily vitamin.
If there is an Epstein formula for success, it is complex and multifaceted but also remarkably unsophisticated in one essential way. When deciding whether to add a player, Epstein focuses most of his attention on an athlete’s personal characteristics rather than just his physical abilities.
Those close to Epstein have a catchphrase for this tactic: “Scouting the person more than the player.”
And the thing Epstein wants to know most about any potential player is how he has handled adversity. It is a question he asks most often during the annual draft of amateur players, an exercise that has been exceedingly good to Epstein.
“In the draft room, we will always spend more than half the time talking about the person rather than the player,” Epstein said. “What are their backgrounds, their psyches, their habits, and what makes them tick?
“And we would ask our scouts to provide three detailed examples of how these young players faced adversity on the field and responded to it, and three examples of how they faced adversity off the field. Because baseball is built on failure. The old expression is that even the best hitter fails seven out of 10 times.”
With the Cubs, the process has led to Epstein taking third baseman Kris Bryant — who may be named the most valuable player in the National League — with the second pick of the 2013 draft. The N.L.’s other top M.V.P. candidate is first baseman Anthony Rizzo, whom Epstein drafted in 2007 with the Red Sox and traded for with the Cubs. Another Epstein draft pick in Boston was outfielder Mookie Betts, perhaps the foremost choice for the American League’s most valuable player.
Epstein was 28 when he took over the Red Sox. Educated at Yale, he talked about simulation methodology efficacy rather than the consequence of a hit-and-run.
Working in a basement bunker instead of the main Fenway Park offices, he presided over two World Series titles in Boston (2004 and 2007), and his innovative tactics were widely studied and copied. But 14 years later, the baseball community is beginning to learn that the one-time upstart has several tricks up his sleeve.
“He really does listen to the human side of all this — it’s not just numbers, by any means,” Cubs Manager Joe Maddon said. “He gets it that there’s a balance between the sabermetric world and the real world. These are human beings and not computers.”
Maddon, 62, praised Epstein for hiring several baseball operations analysts — Maddon called them “the geek department.” But when asked to name Epstein’s strongest attribute, the Cubs manager leaned back in his office chair, smiled and said: “Just ridiculous intelligence. He has this crazy ability to take a situation and reduce it so quickly into its simplest form and then give you the options that make the most sense.”
Although Epstein is a rare presence in the Cubs’ locker room, his players know him well.
“He finds ways to reach out and connect with everyone, and he’s always done that,” said David Ross, the Cubs’ 39-year-old backup catcher who played for the Red Sox during Epstein’s tenure in Boston.
Ross is convinced that Epstein is on a path that will lead to the Baseball Hall of Fame, especially if the Cubs win a World Series under Epstein’s watch. Two famous curses conquered with championships?
“That ought to be more than enough,” Ross said.
But the 2016 Cubs have not won the World Series, or even qualified for it yet. A year ago, they appeared to be on a magical run when they were unceremoniously swept by the Mets in the N.L. Championship Series. The many implausible ways the Cubs have bungled prime opportunities are legend, greater than any fable or fiction.
It is one of the reasons some of Epstein’s friends suggested he pass on the Cubs job in 2011.
“Some thought that if we didn’t win here in Chicago it would invalidate everything we accomplished in Boston,” Epstein said last week. “But I didn’t look at it that way. Not for one second did I think of my legacy. I was taking the job for all the right reasons.”
From the Cubs’ dugout, Epstein nodded toward the famed, sun-splashed and beloved Wrigley Field bleachers. When the Cubs clinched the N.L. Central title on Sept. 16, Epstein, wearing a flimsy disguise, sat in the first row of the bleachers to celebrate with the team’s sauciest fans.
“My fake mustache kept falling into my beer cup,” he said with a laugh, well aware that he had eventually been recognized. “But it was wonderful, sitting out there, feeling the breeze and sitting amongst the fans. Even better than I thought it would be.”
The next few weeks could be less blissful at Wrigley. And Epstein knows it.
“You get wrapped up in it emotionally, and yeah, you can get hurt by the outcome,” he said.
But Epstein is convinced that he has a young roster that will make the Cubs postseason contenders for years to come, which helps assuage his apprehension. Or at least some of it.
“No matter what happens in October,” he said, “this is more of a beginning than an end.”
In the end, it comes back to why Epstein took the job in the first place.
“I saw it as a chance to recreate what I experienced once before,” he said without mentioning the Red Sox. “A chance to do it again for another city that really deserves it. There was something pure about that.
“It is a wonderful chance to do something meaningful.”
Theo Epstein paused ever so briefly, then added: “Again.”
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