Chicago Cubs President Theo Epstein looks skyward during batting practice at Wrigley Field. (Charles Rex Arbogast/Associated Press)

Fourteen years ago, he was unknown, just a face attached to a résumé: Theo Nathaniel Epstein. Yale ’95, worked on the school paper, earned a degree in American studies, University of San Diego School of Law ’00. Insert joke here about whether he shaved. That about covered the totality of what we knew about Theo Epstein then, back when he was named the youngest general manager in the history not just of the Boston Red Sox, but in all of baseball.

Now, we assume we know it all. He is among the game’s most accomplished figures, twice a World Series winner in a city where the culture — the very way of life — had been defined by losing such prizes, often in debilitating fashion. He now sits in the only analogous town, overseeing the only analogous franchise, for which anything is possible this season. If altering the Red Sox’ record of futility, which had dated from 1918, was difficult and monumental and absolutely sob-inducing, what does that make the same task for the Cubs, who haven’t won it all since 1908?

And what if the same guy changes the course of history in both places?

“He’s going to be a Hall of Famer, if he’s not already,” said veteran catcher David Ross, who played on one of Epstein’s teams in Boston and is entering his second season with Epstein’s Cubs. “When this team wins it all, he’s going to the Hall of Fame.”

When this team wins it all. Such is the position into which Epstein has steered these Cubs that the impossible has now unfairly become the expected. It not only makes Epstein one of the most interesting characters in the sport in 2016, but secures his position as a more transformative figure — no longer wunderkind, but sage. As much as Oakland’s Billy Beane received credit for revolutionizing what a GM can be, Epstein altered the perception not only of who could fill this role but of what should be done with it. The season before he was hired by Boston, none of the 30 MLB general managers were Ivy League grads. This season, 10 are, and that doesn’t include Epstein himself, because he is technically the Cubs’ president of baseball operations.

“The job changed, and I think he was certainly a big part of changing it,” said Ben Cherington, who worked alongside Epstein in Boston, then took over the GM’s job when Epstein left. “But the change, in my opinion, has been much less about how old you are and much more about the skills you have and the approach you have to managing every facet of the job. He was at the forefront of that.”

The forefront, when he was an unquantifiable commodity, was Boston, where he and others broke “The Curse of the Bambino” in 2004, then doubled up on the title in 2007. That experience couldn’t be replicated for the same team in the same town, because a curse doesn’t reappear in a single lifetime. The part that mattered — people coming up on the street, saying how their dad lived to see it, but their grandfather hadn’t, but it was okay because the family hung a pennant on his grave — could only be replicated with one other team, in one other town.

“It resonated with me so much, because it had so much meaning and relevance to what you do,” Epstein said. “At that point, I kind of had Chicago in the back of my mind. Maybe someday, that would be so wonderful to do that there, taking what I’ve learned here and applying it to that situation.”

Hard-earned New England angst has been traded for a Midwestern strain of the same, hexes of billy goats replacing those of Babe Ruth. As he spoke about all this early in spring training, he wore Cubs athletic shorts and a Cubs T-shirt. A few of his players finished up some extra hitting following a morning workout. The breeze was calm, the sun was out. And Theo Epstein sat, relaxed and perfectly poised, because he is at that point in his life where he can both look back for plenty of perspective and ahead for new experiences, new dreams.


Theo Epstein speaks with Red Sox owner John Henry before Game 1 of the 2003 ALCS. (Mike Segar/Reuters)
‘I’ll get the job done’

This wasn’t a dream so much as a mission. The day after Epstein graduated from Yale, he boarded a flight to San Diego, parlaying two successful summers as an intern with the Baltimore Orioles into another internship, this in the public relations department of the Padres. Turns out, baseball operations was just down the hall.

“He hung around — a lot,” said Kevin Towers, then the Padres’ general manager.

Towers told Epstein the best way to learn the sport would be to sit, every night, behind the plate, run the JUGS gun that measured velocity and chart pitches. He could learn how a two-seam fastball looked different from a four-seamer, how a hard curveball broke differently from a slider.

“He wanted, really, just to make a statement early,” Towers said. “ ‘Whatever you want me to do, I’ll be good at it, I’ll get the job done, I’ll do it quickly and it’ll be great.’ ”

Part of the Epstein lore is that his talent and intellect were so immense that he could simultaneously balance a more-than-full-time job with law school. That’s largely true, but so is this: “I didn’t go to class,” Epstein said.

By Epstein’s telling, San Diego’s ownership wanted Towers to consult with the club’s counsel more frequently. “That was anathema to him,” Epstein said. Towers’s solution: Send young Theo to USD — kind of.

“I chose my classes based on which professors did not take attendance, and then I traded Padres tickets for notes from class,” Epstein said. “I wasn’t the student of the month.”

He did graduate, however, legitimizing the description of him as this Ivy League-educated lawyer who happens to run a baseball team. He’s also the kid who drilled down on numbers before drilling down on numbers was part of the routine of a baseball front office.

In 2000, three years before “Moneyball” was published, here was Epstein, rushing into Towers’s office, urging his boss to pick up a minor league shortstop who was placed on waivers by Boston, a kid named David Eckstein. Towers looked into Eckstein. He was 5 feet 7. “This guy’s a gnat,” Towers said.

Epstein was undeterred. Look at the way his on-base percentage is trending, he said; consider the park factors.

“I didn’t know what park factors were,” Towers said. The Padres passed. Two years later, Eckstein was the starting shortstop on the Angels team that won the World Series. Four years after that, he was the World Series MVP for the Cardinals.

“I was like, ‘Wow; maybe I need to start paying attention to what this guy’s putting in my ear,’ ” Towers said.

At the same time, Epstein knew he had to pay attention to what Towers was putting in his ear. So when Towers would travel to scout prospects across Southern California, Epstein went, too. He watched, listened, asked, learned. At the same time, Towers and others with the Padres noticed another aspect of Epstein’s character, one they couldn’t teach. As Epstein’s relationships in the sport grew, Towers would consistently hear back, from agents and athletes, coaches and colleagues: “I really enjoyed dealing with Theo.”

“He was able to blend into pretty much any situation and just be comfortable and fit,” said Craig Shipley, an infielder with the Padres when Epstein was an intern, a scout as he moved into the front office.

Epstein became San Diego’s director of baseball operations. Others sought him. A Los Angeles law firm wined and dined him, offering him a $140,000 salary when the Padres were paying $35,000. Towers got Epstein’s salary doubled. He stayed. Then the Blue Jays called, wondering about an assistant general manager’s job.

His trajectory was so obvious that Towers eventually asked him: If you could run any club, which one would it be? Epstein grew up a mile from Fenway Park in the Boston suburb of Brookline, spent summer evenings glued to Sox games on TV, writhed on the floor alongside his twin brother, Paul, after the sixth game of the 1986 World Series. His answer was instant: “The Boston Red Sox.”


Epstein speaks to the media following the Red Sox’ collapse in the final month of the 2011 season. (Bizuayehu Tesfaye/Associated Press)
Bold, or stupid?

Following the 2002 season, the Red Sox — under a new ownership group that included Epstein mentor and champion Larry Lucchino as president — tried to woo Beane to be the GM, but failed. So they turned to Epstein, a stunning move at the time. The narrative: Here, kid, this franchise hasn’t won a World Series since 1918. Take a crack.

“It was a heavy, heavy weight that kind of hovered over the organization,” said Cherington, who worked for the Red Sox before Epstein arrived. “For a 28-year-old at the time, that had to be a lot of pressure.”

Said Epstein: “As I look back on it, I had no idea what I was getting into.”

But from the first day, Epstein took measures to alleviate the burdens. He formed not a front office but “almost like this fraternity of guys” who worked 100-hour weeks, had really nothing else going on in their lives and obsessed about the Red Sox, about baseball, about finding an inefficient aspect of the market they could exploit. His father, Leslie, gave him a piece of advice upon accepting the job: “Be bold.”

So Epstein’s Red Sox sent interns to NCAA headquarters in Indianapolis to photocopy 30 years’ worth of college baseball stats, a search for clues about what characteristics of college players translated into becoming productive major leaguers. They partnered with neuroscientists in Cambridge, Mass., to try to figure out what the brain of an outstanding hitter looks like, and worked cognitive development into their farm system. They sent out a survey to every scout and player-development employee at the end of each season, asking for input on what the franchise could do better, soliciting off-the-wall ideas about players to pursue or practices to employ.

And they began to use a pair of mantras around the office. The first — “We don’t know [crap]” — kept them humble when they thought they were rolling. The second — “We cannot be afraid to look stupid” — kept them pushing forward, being bold.

This band of brothers — Cherington and Jed Hoyer and Josh Byrnes and Peter Woodfork and so many others — grew remarkably tight. This wasn’t coincidence. Epstein was having an impact that had nothing to do with analyzing players.

“He kind of raised the bar around the office just through his conversation, no matter who you were,” Cherington said. “. . . And then, and this was important: He also made it fun.”

There was no end to what form this might take. They hit golf balls in the office while spit-balling ideas. Epstein could, and did, perform impressions of anyone and everyone in the room. An intern was harassed so badly that a stapler, likely thrown by Epstein, “hit him in such a way that he might have been stapled,” Paul Epstein said.

“That frat-house culture, that frat guy, that’s as much of what Theo is as anything,” Paul said. The pinnacle (or nadir, depending on your predisposition) came in the spring of 2004, entering Epstein’s second year as the GM. Eight front-office members rented a mammoth house in Cape Coral, a 20-minute drive from the Red Sox’ spring home in Fort Myers, Fla. The team’s clubhouse manager dubbed the place “Phi-Sign-a-Playa.” These guys got up and carpooled to the ballpark — Hoyer and Epstein blasting the White Stripes on a continuous loop, to the point where Hoyer can’t hear “Seven Nation Army” without thinking of that spring. They ran a baseball team, worked out, grabbed takeout, drove home, played poker, drank beer and relentlessly pulled practical jokes.

“We had,” Hoyer said, “an absolute blast.”

A dozen years later, Epstein describes himself as “allergic” to business school slang, to the kind of pabulum espoused in leadership books. But he knew, too, that a successful organization needed a culture that wasn’t just driven by one or two people, but was supported by the whole.

“None of us were putting our careers or our next step ahead of us,” he said. “We were just kind of like overwhelmed and shocked that we were in this position to begin with. So, let’s make sure we get it right.”

To get it right, they needed to be bolder than some thought was wise. In the summer of 2004, the front office watched Boston’s defense devolve into what it considered a fatal flaw. So the Red Sox dealt Nomar Garciaparra, perhaps the best shortstop in franchise history, in a four-team trade that brought back shortstop Orlando Cabrera from Montreal and first baseman Doug Mientkiewicz from the Minnesota Twins. Bold, or stupid?

The day of the deal, Paul Epstein was listening to Boston sports talk radio. “He traded No-mah foah a paiah of .230 hittahs!” Paul called his brother: “What did you do?!” After the news conference, Theo walked into the office. It was a Saturday. His colleagues had all gone home. The TV flickered with a headshot of a smiling Garciaparra, a Cubs hat superimposed on his head.

“That was a lonely feeling,” he said. That night, for the first time, he took an Ambien.

The trade, though, worked brilliantly. The Red Sox went 21-7 in August, secured the wild-card playoff berth, stormed back from a three-games-to-none deficit to beat the Yankees to take the pennant, and won the World Series, breaking the curse. Three years later, with important pieces Epstein’s front office had drafted and developed (Dustin Pedroia, Jon Lester, Jacoby Ellsbury), they won again.

Not all of Epstein’s moves worked out. He signed Edgar Renteria to play shortstop in 2005 but traded him after a single ineffective season, just one member of a rotating cast at that position. Right-hander Daisuke Matsuzaka was an expensive import from Japan who was a part of the 2007 champions and had a sterling 2008 but was largely injured and ineffective thereafter. The fan base, for so long expecting the worst, now expected October baseball annually. Each move was parsed.

“He was sort of in the crosshairs there the entire time he was there,” Hoyer said.

Subtly and perhaps subconsciously, Epstein gave off signals that his time there could end. He had long referenced the philosophy of legendary football coach Bill Walsh, who believed coaches and executives should move on after a decade with the same organization. Epstein’s contract ran through 2012. As 2011 approached, some colleagues wondered whether he might pursue something outside baseball. Epstein, by then, was married and had his first son. He had a passion for music and had founded, with Paul, a foundation to help urban children. He had grown up. But could he actually outgrow the Red Sox?

At some point during this period, Epstein attended a funeral for a longtime club employee. The program bore a Red Sox logo. By Epstein’s memory, the coffin did, too. What had been so invigorating, so perfect, became, to a degree, suffocating. He told his wife, his close friends: “I don’t want to be buried in a Red Sox casket.”


This year’s Cubs open the season as a team with 22 of 25 players acquired since Epstein’s arrival. (Jonathan Daniel/Getty Images)
A new dawn

In the summer of 2011, when Tom Ricketts needed a new person to oversee all aspects of the Chicago Cubs’ baseball operations, he attacked the problem in two ways: enlisting two independent quantitative analysts to research which clubs ran most efficiently and produced the best results; and reaching out to other owners and some general managers, ending each chat with one question: If contracts and money were no issue, who should I interview?

As one high-profile general manager told Ricketts: “You’re going to need someone with a track record if you’re really going to affect a cultural change in your organization. You have to get a lot of people to follow.”

Epstein by then had that track record: The Red Sox, who had averaged better than 93 victories in his nine years as general manager.

Ricketts asked the Red Sox for permission to speak to Epstein, then asked Epstein to meet him at a Manhattan apartment his family owned because a sighting in Boston or Chicago — or even a midtown restaurant — could be explosive. The Epstein that arrived was somewhat colored by his immediate past. The 2011 Red Sox were built to win and were in first place at the end of August. To make the playoffs, they needed to win just seven games in September. They won six.

“It was so crushing, and so emotional, and so oppressive emotionally, really,” Epstein said.

Whether it was that experience, or Epstein’s nature, or some combination, Ricketts encountered an extraordinarily self-critical, almost vulnerable, job candidate. “It was a very atypical interview,” Ricketts said. Epstein picked apart his own record, concentrating more on what he might have done differently in Boston than on the two titles. He also emphasized this was not an individual pursuit, that he would need the highest-caliber team around him.

When Ricketts hired Epstein later that month, he discovered how quickly and effectively he would build his front-office team, hiring old pals Hoyer as the general manager and Jason McLeod away from San Diego to lead the Cubs’ scouting and player development departments.

“A lot of people think that this was some kind of math problem,” Ricketts said. “The fact is, while it certainly is important to understand what stats can tell you about a player and his potential, the strength of Theo and Jed and Jason is they get past that. They get to understand what motivates a player.”

Together, they built a plan to rebuild Chicago’s minor league system. Three summers in a row, they traded away 40 percent of the Cubs’ rotation. Epstein’s Red Sox had never lost more than 76 games in a season. His first three Cubs teams lost 101, 96 and 89 games, respectively. The Chicago Sun-Times previewed the 2012 season with an image of Epstein walking across water. By the end of the same season, the paper published the same image, only with Epstein’s head barely above the surface.

“That was really hard to go through,” Epstein said. But there were pieces of the process that were enormously satisfying. All these years after Towers took him on those scouting missions, the part of his job Epstein enjoys the most is evaluating players for the draft. He loves the competition. He loves how important it is to the development of an organization. And in a way, he loves arguing not only about players, but about the best processes for evaluating them.

“There’s nothing I hate more than someone who speaks in the draft room with absolute conviction, but they have nothing to back it up,” he said. “It’s like, ‘No! That’s your opinion. It’s not the truth!’ . . . I just love the process of trying to strip away as much error, as much doubt, as much subjectivity that we can make every pick count.”

This year’s Cubs open the season as a team with 22 of 25 players acquired since Epstein’s arrival, including their first-round draft picks from 2013 and ’14, Kris Bryant and Kyle Schwarber. Throw in the fact that 13 players on Boston’s opening roster were acquired during Epstein’s tenure there — including six from the 2011 draft, Epstein’s last with the Red Sox — and it’s hard to think of a character who has had more impact on the entirety of the 2016 season.

“It’s a pleasure to watch him now,” Hoyer said. “He’s so talented, so polished. His relationships with people in the game are so good. I think a lot of it is: He’s done the job for a long time now. But it’s also how he handled himself under pressure early on that turned out to be kind of a great springboard.”

Epstein’s first five-year deal with the Cubs expires after this season. “I’m not concerned,” Ricketts said. They will get a deal done, but how long will it last?

Epstein still believes in Walsh’s words, and by that standard, he would be nearly halfway done in Chicago. What’s next?

Why not look at what’s now? A new baseball season is about to dawn, and the Cubs — yes, the Chicago Cubs — are World Series favorites.

“I look no farther than that,” Epstein said. “That’s quite a place to look. ”