The Rainmaker: How Cubs boss Theo Epstein ended a second epic title drought

Chicago's team president arrived after the 2011 season with a mandate to do something the organization hadn't accomplished in more than a century. Here's how Theo Epstein turned the Cubs into World Series champions.

This article appears in the Dec. 19, 2016 issue of SPORTS ILLUSTRATED. To subscribe to the magazine, click here.

There’s magic in the ivy and the old scoreboard
The same one I stared at as a kid keeping score
In a world full of greed, I could never want more
Than someday we’ll go all the way

—Eddie Vedder, “All The Way” (2008)

An amateur guitarist,bibliophile and former Yale Daily News sports editor, Theo Epstein was the rookie general manager of the Red Sox when he first met Eddie Vedder. It was July 2003. Epstein was sitting at his Fenway Park desk when his secretary told him, “George Webb from Pearl Jam is on the phone.”

Webb was the band’s equipment manager. He had heard that Epstein considered Pearl Jam his favorite band ever since its debut album, Ten, in 1991. Webb arranged for tickets to a concert in Mansfield, Mass., for Epstein and his own “band,” the whiz kids in his baseball operations office. After they watched from the wings, Epstein invited Webb and the band to take batting practice the next morning at Fenway Park. So excited was lead singer Vedder, a Cubs fan who grew up in Evanston, Ill., that he went to sleep with his glove near the nightstand. Alas, thanks to some postconcert libations with the warmup band, the Buzzcocks, Vedder slept through the Fenway fun.

The next night Epstein and his crew returned to Mansfield for the second show. That’s when he was introduced to Vedder. Epstein needled him about sleeping through the chance to hit at Fenway. “Friends ever since,” Epstein says.

That year, at 29, Epstein stood on the cusp of making it big—Pearl Jam big. Seven months earlier he had become the youngest general manager in baseball history after Blue Jays general manager J.P. Ricciardi and A’s GM Billy Beane turned down the Boston job, and told the Red Sox’ owners they should give it to Epstein, then their assistant GM.

It wasn’t just Vedder’s thoughtful, piercing music that appealed to Epstein. When they met, he was the same age Vedder had been in 1994, when his reaction to enormous fame—the release of a third platinum-selling album just months after he appeared on the cover of Time—was akin to treating a wildfire: You had to tamp down the beast, not stoke it. The band refused, for instance, to produce music videos. Building an image can create expectations of what a person should be, and those expectations, and the falseness of them, Vedder told Melody Maker that year, “just start tearing you apart.”

Epstein shared the same ethos. Upon being named Boston GM, he had turned down offers to appear on The Tonight Show with Jay Leno and the Late Show with David Letterman. “It felt wrong at that point,” Epstein says. “I would have been on as a reward for being a young GM—a novelty, a gimmick. Even though it was appealing on the face of it, I passed on all that.

“Once you thrust yourself out there in the public domain, it’s really hard to retreat, to say no or reclaim that certain part of your life as private. It’s hypocritical to say when things are going well, ‘Interview me. Ask me how great I am. Ask me about family and personal life.’ At some point later when someone wants information and you want to draw the line, how do you do that?”

Ian Johnson/Icon Sportswire

In spring training of 2004, when Epstein and eight of his baseball ops bandmates rented a place in Cape Coral, Fla.—filling it with laptops, poker games, Mexican beer and a youthful energy and intellect that would change the game—Epstein declined a request from SI for a group photo at the house known as Phi Sign-a Playa.

“We haven’t done anything yet,” he explained, before his Sox won the franchise’s first title in 86 years that season, then earned another in 2007.

The nightly talk shows, as well as the morning news shows, came calling again last month after Epstein, in his fifth year as president of baseball operations of the Cubs, ended an even bigger drought than the one in Boston: He presided over their first World Series title in 108 years. Again, he declined the offers. Instead, on Saturday, Nov. 5, the day after the championship parade in Chicago that drew millions of people, Epstein and Jed Hoyer, his GM and close friend, were in the office preparing for the general managers’ meetings.

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“Eddie Vedder has been a really good model, and not just him, but the whole band,” Epstein says. “They’re great at carving out just enough space for their music, their art and their fans. They created their art, they enjoyed it, and they made sure their fans enjoyed it.

“They didn’t make music videos just to broaden their appeal, because that would get in the way of their art. There’s a real lesson there. Be intentional about the spaces you create but not at the cost of compromising other elements. I’ve gotten to know [Vedder] extensively, but everything I need to know I can see by the choices he makes. I’ve been around him long enough to know how the [band members] create careers, but at the same time their lives and families reflect their values appropriately. It comes back to being genuine, slowing things down, being thoughtful of others and being true to yourself.”

Epstein turns 43 this month. In only 14 years as a chief architect, his teams have won three World Series and made the playoffs five other times. That is beyond a lifetime’s worth of achievements for almost any baseball executive, but it is sui generis when you consider the mythology he conquered three times over. First in Boston and then in Chicago, Epstein won world championships that could not be won in the combined 194 years before he took his turn. His third conquest, which spanned both jobs, was not just ending the war between traditional scouting and the guerilla uprising of analytics but also melding those factions into what he likes to call “a scouting and player-development machine.”

He is King Arthur pulling swords from three stones—except “king” would be a bad place to start for someone taking a lunch break in a denim Pearl Jam cap, plaid shirt, jeans and boots while making his way through coffee, eggs, chorizo and a key lime vinaigrette-avocado salad at Uncommon Ground, a Wrigleyville eatery with an emphasis on organic ingredients.

His money, of course, is no good here. The bill, amounting to zero, will be presented with sincerest thanks for building a Cubs team that won the World Series three weeks earlier.

Al Tielemans

In the one pointed departure in his otherwise sweet love song to his Cubs, Vedder made sure to frame his wish “in a world full of greed.” It’s a reminder that he doesn’t want what so many achievers of this age want: the extras, the parasitic trappings of achievement. What does Epstein want? Where does he go from here? How did he pull this off? The clues to that last question, at least, can be found in an assessment from Joe Maddon, the manager he hired two years ago as a key piece of his years-long rebuild in Chicago.

“One word: empathy,” Maddon says.

Epstein had interviewed Maddon, then the Angels’ bench coach, for the Red Sox’ job after the 2003 season. He hired Terry Francona instead because he wanted a manager with experience, but he turned back to Maddon, who had gone on to the Rays, after the ’14 season when he needed a seasoned hand to bring the same upbeat, authentic vibe to the major league clubhouse that existed in the Cubs’ player-development system. (In hiring Maddon, Epstein took advantage of the rare opportunity of an elite manager’s free agency, but that meant he had to replace the incumbent, Rick Renteria. Epstein insisted that he write part of the press release himself to stress his high regard for Renteria. “That wasn’t easy,” Epstein says.)

As a newly minted world champion, Maddon recently leaned back in a booth at Ava, his Tampa restaurant. He knew one word wasn’t enough to describe the Cubs’ president.

“He’s brilliant, he’s sabermetrically inclined, he understands old-school-scouting techniques, he understands the game,” Maddon says. “But of all the guys I’ve met, he’s more empathetic than all of them. He understands people.

“When you have a conversation with him, it isn’t sterile. There’s feel. Feel is a part of his method. We get involved in [analytics], but we never get involved in that to where other stuff doesn’t matter. I might even be the cold one, and he comes in with the warm and fuzzy to me, which normally never happens from the GM.”

Tom Ricketts bought the Cubs in 2009, when they lost 14 more games than they had the previous year. They lost nine more the year after that, and four more the year after that before he hired Epstein away from Boston.

“The reason he’s successful is he has a great leadership style and an eye for talent,” Ricketts says, “but an eye not so much for how a slider breaks but for people who work collaboratively, and he engages them. There’s an element of those soft skills that would cause some people on the baseball side to roll their eyes, because he’s very concerned about the character of players he signs and the atmosphere in the clubhouse. Is the player going to be additive or does he subtract? What I see is someone who treats people well.”

Empathy? Ricketts had to laugh when told of Maddon’s assessment: “I made the joke one day, when [Epstein] first got here and he had to let some people go. I told him, ‘If I ever have to be fired by anybody I hope it’s you.’ It’s his empathy.”

Empathy? Epstein didn’t laugh when he heard the word Maddon used. He fell silent, gave thanks and then, after giving it proper study, tried to explain it. He remembered what his parents told him about how he would drive himself crazy as a young child with thoughts of mortality. That someone he loved could die seemed so heavy and unfair to him. He next thought about writers—the Russian novelists, Dickens, Faulkner, Hemingway and the other greats that were as much of a part of his childhood as baseball.

Epstein’s father, Leslie, is an acclaimed novelist who chaired the creative writing program at Boston University. His grandfather and great-uncle wrote the screenplay for Casablanca. An Epstein house rule stipulated that every minute spent watching baseball on television had to be equaled by reading books.

“A doubleheader,” Theo says, “was a lot of reading.” The material, nuanced and evocative, nurtured compassion. One more piece of data he considers: “Maybe it’s part of being a twin. I’m a twin. [His brother, Paul, is a social worker at Brookline (Mass.) High, their alma mater.] My mom’s a twin. My grandfather’s a twin.”

Epstein turned to writing at Yale, but the solitude did not suit him. He wanted a collaborative life.

“When I was writing or competing in individual sports, it felt unfulfilling and lonely,” he says. “When I was able to find a group of people I believed in and liked, that all worked in pursuit of a common goal, it felt incredibly rewarding.”

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While still an undergraduate Epstein took an internship under the Orioles’ president, Larry Lucchino. He later followed Lucchino to the Padres, where his desk served as the DMZ in a burgeoning war, smack between the analytics guru and the scouting director. They couldn’t stand each other and rarely spoke, but both of them enjoyed the company of Epstein. In 2002 he followed Lucchino to Boston.

The curse-busting championship came two years later, unleashing a catharsis across New England unmatched in baseball history. It was in the wake of such emotional outpouring that the idea of someday running the Cubs first occurred to Epstein, if only in a fleeting manner.

“As far back as the aftermath of the ’04 World Series, I would talk about it with my friends a little bit—‘If I ever move on, the Cubs would be the one spot because it was so powerful to win in Boston,’” Epstein says. “The best aspect of the job was seeing how much it resonated with people and families. You never let go of that. It adds meaning to the whole thing.”

The glow in Boston eventually waned. The Red Sox won 95 games the next year but were swept in the Division Series. Rather than sign a contract extension, Epstein resigned on Halloween, escaping the media by slipping out of Fenway in a gorilla suit. He came back a few months later and won another title in 2007, but under the groaning and growing weight of expectations he began falling out of love with his hometown team.

The 2010 season especially buckled him. Epstein caught flak for mentioning that it could be a “bridge” year in which he kept one eye on long-term development. That season he had an epiphany while attending the funeral of a long-time team employee. Funeral pamphlets included the Red Sox’ logo. The deceased rested in a Red Sox casket.

“I remember thinking, I really don’t want this to be me,” he says. “Because when you’re not unconditionally in love with a place any more, I think you resent to a certain extent the degree to which you’re identified with that place, or you self-identify with that place. So I just began to distance myself from it a little bit emotionally.”

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In 2010, Boston won 89 games and missed the playoffs for a second time in his eight seasons. Early the next season, with a year left on his contract, Epstein told the Red Sox’ owners about the “internal conflicts” he was experiencing.

In August 2011, Ricketts fired his general manager, Jim Hendry. He spent the next few weeks canvassing 20 people he knew in baseball on the best person for the job, regardless of contract status. Nineteen of them told him Theo Epstein.

Epstein’s Boston team collapsed that September, losing 20 of its final 27 games to spit away a playoff spot. Ricketts waited only two days after the final loss to call Red Sox owner John Henry and ask for permission to talk to Epstein. The next night the two of them were having dinner at the owner’s New York City apartment overlooking Central Park. A Phillies-Cardinals playoff game played on the television. Ten minutes into the conversation both men knew this was a perfect fit. Epstein had to divorce his hometown.

“I blame myself for this more than anything,” Epstein says, “because I hate it when people blame their environment. Especially in a leadership position, you’re responsible for how you react to your environment and how you change your environment, and for being a positive force to change it for the better if you think something is toxic.

“I wouldn’t blame anyone else for it. I know everyone said, ‘Well, it was you and Larry, it was a power struggle.’ It really wasn’t. Our dynamic never really changed. He never got super involved in baseball operations, but he was my boss and always had the right to question me on things, and I never really resented that.

“It wasn’t any one person. It was just the weight of the nine or 10 years in Boston.”

The Cubs opportunity removed all the weight. It was a chance to figuratively return to Cape Coral, only with much more accumulated wisdom.

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One of Epstein’s guiding principles in Chicago would be considering the character of the players he acquired.

“I used to scoff at it, when I first took the job in Boston,” Epstein says. “I just felt like, You know how we’re going to win? By getting guys who get on base more than the other team, and by getting pitchers who miss bats and get ground balls. Talent wins. But ... it’s like every year I did the job, I just developed a greater appreciation for how much the human element matters and how much more you can achieve as a team when you have players who care about winning, care about each other, develop those relationships, have those conversations. It creates an environment where the sum is greater than the parts.”

When Epstein needed to fortify his bullpen in July, he traded for Aroldis Chapman from the Yankees, but not before, he says, satisfying his concerns about Chapman’s character. Chapman served a 30-game suspension at the start of the season for his behavior in a domestic incident on Oct. 30, 2015, in which after an argument with his girlfriend, he fired eight shots from a gun in his garage. Epstein and owner Tom Ricketts insisted on speaking to Chapman on a conference call before agreeing to the trade. They told Chapman they held their players to a high standard and needed to hear from him that they could fully expect him to meet those standards. Chapman assured them he had learned from it and would meet their expectations.

Back in January 2012, Epstein summoned every manager, coach, scout, instructor, trainer and baseball operations person in the Cubs’ organization to a budget hotel in Mesa, Ariz., for a four-day summit. They spent one day on hitting philosophy, one day on pitching philosophy, one day on defense and baserunning philosophy—and one day on character: “What types of human beings we wanted and what our expectations would be for players, how we want them to behave,” says Epstein.

From the summit Epstein crafted a 259-page spiral-bound book that would be the “living, breathing document” to define his organizational doctrine. He called it The Cubs Way: 2012 Player Development Manual.

The first page of the first chapter established six “Department Principles.” The first principle read, “We will treat the development of every player as if we were making a personal investment in him.” The sixth and final principle was this: “At all times we will keep this in mind: Our mission is to help the Chicago Cubs win a World Championship!”

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Epstein delivered the championship in his fifth season. He did so with a core of young position players—eight under the age of 28 played in the seventh game of the World Series, a record—and a staff in which not one homegrown pitcher took the mound in the postseason. The defining moment occurred during a rain delay in Game 7, tied with the Indians after nine innings: The Cubs packed shoulder-to-shoulder for a players-only meeting in a small weight room behind the visiting dugout at Progressive Field—a strong visual of Epstein’s ideals of collaboration and character.

To that group, Epstein has since added free-agent centerfielder Jon Jay as a replacement for Dexter Fowler, let Chapman leave for the Yankees as a free agent and traded outfielder Jorge Soler to the Royals for closer Wade Davis. The work goes on. From his tiny room in the team’s temporary quarters on North Clark Street, Epstein can hear the construction of the building next to Wrigley Field that next year will house the new offices. He has arranged to have a modern, sprawling common area—similar to the hip clubhouse digs that opened this year—with a wall of television screens. He lives a 10-minute walk from Wrigley. Married with two children, Epstein will walk home during visitors’ batting practice for night games, have dinner with his family, then walk back in time for the first pitch. He has never been happier.

“This place is amazing,” he says. “So many people have worked so hard at building this up, there is no place else I’d rather be. The Cubs won back-to-back [World Series] in 1907 and ’08, and that’s a great short-term goal. I’m signed through 2021. It would be wonderful if this team gets to October with a chance every year. We feel like this is just the beginning.

“I love being around these players and the people I work with. It’s fun to come to work every day.”

He found magic in the ivy. In October, many hours (and more libations) after the Cubs won their first pennant since 1945, beating Clayton Kershaw and the Dodgers 5–0 at Wrigley Field, two men slipped onto the diamond in the hush of the empty ballpark. It was five in the morning, about two hours before sunrise. They played catch and took batting practice. In those small hours of a historic night, carefree, Eddie and Theo looked not like the rock stars we expect but like children at play.