by Tom Verducci
Ricketts had met Epstein only once before, in passing at a baseball owners meeting. “My first concern,” Ricketts said, “was what kind of person was he.”
Ricketts knew all about Epstein’s reputation. He expected a quant, someone who spoke with religious fervor about the power of numbers. He also expected someone with the air and attitude of a big shot, with an ego emboldened by winning two World Series titles as general manager of the Boston Red Sox, the first of which, at age 30, ended a supposed curse 86 years in the making.
“He was like Cher or Bono: people knew him by just one name—Theo,” he said. “You wonder what kind of ego he had.”
At dinner that night he immediately found Epstein to be different from the person he had expected. He found a humble, 37-year-old man who spoke with more passion about people than about numbers.
“I don’t know what you think I am,” Epstein told Ricketts, “but I’m not what people think I am. It’s not about me. It has to be about the whole organization. To win you have to have a lot of people rowing in the same direction.”
Ricketts would say later that he knew after just 10 minutes that he had found the right person to rebuild the Cubs.
“I was getting a good read on what kind of manager he would be, how he treats people,” Ricketts said. “I’ve been in businesses where you hire really talented people, but they end up mistreating people beneath them. That is very uncomfortable.
“We spent a few hours, we had dinner, watched a little baseball, and it became clear who he was. He was the kind of person who treats people with respect. He was honest and candid about his successes and failures. A lot of people defend themselves so that every decision looks like a tough one. Theo doesn’t get defensive. He gets very honest about it.”
Likewise, Epstein discovered in Ricketts an owner who defied the expectations he brought to the meeting.
“I was really impressed with him personally, being humble and down-to-earth and easy to talk to, all the things you don’t expect from a rich guy,” Epstein said. “I was impressed by his desire to find someone to build a foundation and create a healthy, winning baseball operation, not look for a very quick fix for the 2012 Cubs. He seemed to know what he wanted, which was a modern, robust, thriving, healthy baseball operation, but he didn’t know how to get there, and he had taken a lot of steps to do the search the right way to find the right person.
“We talked baseball and it was clear that he knew what he didn’t know, but that he would also be very supportive and very patient and it seemed like he would be an easy person to get along with. He painted it very much like the blank canvas that it was. He wanted to develop a vision and a strategy.”
The meeting went very well, but one key question remained, a question Ricketts kicked around in his head ever since he announced the firing of Cubs general manager Jim Hendry on August 19: Would Epstein actually leave Boston, his hometown, and with one year remaining on his contract?
The Cubs, in keeping with unwanted form, were a mess. The 2011 team lost 91 games while walking more batters and making more errors than any team in the league. A Cubs fan could shrug at the numbing familiarity of such ineptitude. Since 1945, when the Cubs last played in the World Series, losing seasons outnumbered winning seasons 45–19, with another two at flat even.
A century ago the Cubs were a dynasty. Led by the melodious double-play combination of Joe Tinker, Johnny Evers, and Frank Chance, the Cubs from 1906 through 1910 won four pennants and two World Series, while averaging 106 wins per year. Years of malaise and misadventure followed—so many years that the more optimistic of fans liked to crack, “Anybody can have a bad century.”
Winning seasons happened for the Cubs like freak snowstorms: you never saw them coming, and they ended as quickly as they arrived. Those isolated times of success served only to set up epic, inglorious failure. The 1969 team suffered a 17–26 collapse, highlighted by a black cat scampering in front of their dugout September 9 in New York; it would be the last night the Cubs spent in first place that year. The 1984 team, needing one win to advance to the World Series, lost three straight games to the San Diego Padres in the National League Championship Series. The 2003 team reprised the collapse, losing three straight potential NLCS clinchers to the Florida Marlins, a downfall in which Bartman had an infamous hand.
Over the years, two ancient forces bound Cubs fans. One was Wrigley Field, the former site of a Lutheran seminary, where the Cubs have been playing baseball since 1916. With its bucolic beauty and a coziness as comforting as a grandmother’s hug, Wrigley, especially on a warm day with a cold drink, was the perfect diversion from the other force: the unrequited yearning for a World Series championship.
Ricketts was the third owner to inherit those forces, following P. K. Wrigley, who ran the team from 1932 to his death in 1977, to the Tribune Company, which purchased the team from the Wrigley family in 1981. Ricketts also inherited Hendry, who upon his firing had been with the Cubs for 17 years, the last 10 seasons as general manager. His teams had won division titles in 2003, 2007, and 2008 under managers Dusty Baker and Lou Piniella, high-profile, old-school types who were the dominant personalities of the organization. But little about the organization was sustainable. After getting swept by the Dodgers in the 2008 Division Series, the Cubs in 2009 dropped from 97 wins to 83 wins. During that 2009 decline, Ricketts purchased the team.
Ricketts, the director of TD Ameritrade Holding Corporation, is the son of J. Joseph Ricketts, who established Ameritrade in 1971. The younger Ricketts became, like many fans, an ardent supporter of the Cubs in the magical playoff season of 1984, when he moved from Omaha to attend the University of Chicago. Ricketts would later live with his brother Pete on the corner of Sheffield and Addison, and he would meet his future wife, Cecilia, in the Wrigley Field bleachers. He deeply understood Cubs culture, and what a championship would mean to the fans.
The slide of 2009 begat the slide of 2010, when the Cubs dropped to 75 wins, which begat the slide of 2011, when they sank to 71 wins. On July 22 that season, Ricketts decided to fire Hendry. He informed Hendry of the decision, though he made no announcement at the time. Hendry agreed to keep the firing secret so he could stay on through the August 15 deadline to complete the process of trying to sign his selections from the June draft.
Hendry went out in a blaze of cash. On August 16 the Cubs announced they had signed 18 of their top 20 picks, many of whom were signed for bonus money that exceeded the recommendations of the commissioner’s office, known as “slot” money. There were no penalties associated with “going over slot,” other than incurring the wrath of commissioner Bud Selig. The slotting system was an unofficial strategy by baseball to try to curb spending on draft picks. But, by rule, teams could still flex their financial muscle to convince players to sign, especially the talented players who slid lower in the draft because of demands for an especially high bonus. Drafting players in later rounds and convincing them to sign with first- or second-round money was a popular tactic with higher-revenue teams, including Boston under Epstein. It was a tactic Hendry used on his way out from the Cubs in 2011.
Hendry’s signings included first-round pick and high school infielder Javier Baez, who signed for $2.625 million, and Dillon Maples, a high school pitcher with first-round talent selected in the fourteenth round. (He slipped in the draft because teams considered him a difficult sign because of his scholarship offer to play football at North Carolina.) The Cubs signed Maples for $2.5 million, the largest bonus ever paid to a player drafted lower than the second round.
(Maples would turn out to be the more typical Cubs draft pick. Two days before reporting to a post-draft mini-camp, Maples felt a twinge in his forearm while using the TV remote control. He was diagnosed with a strained ligament in his forearm. The Cubs gave him a rehabilitation throwing program, but Maples did not strictly adhere to it. He developed “Steve Blass Disease,” slang for the sudden, mysterious difficulty throwing strikes, which is named after the former Pi
ttsburgh Pirates pitcher. In five years, none of them out of Class-A ball, Maples hit or walked 151 batters in 182 innings and threw 47 wild pitches.)
Three days after the signings, on August 19, 2011, Ricketts announced the firing of Hendry. Ricketts had no successor in mind yet, he said, but he did have specific ideas about what he was looking for in a top baseball executive.
“When I look at the candidates, I kind of see a couple of criteria,” Ricketts told reporters. “I see, number one, they’ll have to share a commitment to player development, which obviously is the key to consistent success. I think we can look for guys that have a little stronger analytical background than maybe some of the guys we have here. Someone who has worked with some of the new tools—that would be a plus.
“And then someone who’s been in a winning culture and who can bring the lessons of that over and has a track record of success. The sabermetric stuff is important, but it’s just a piece. We’re not running the baseball organization by a computer model.”
Ricketts’s three major criteria—a commitment to player development, an analytical background, and a track record of success—made for an exact definition of Epstein. The media, though, did not immediately pick up on the possibility of Epstein leaving Boston for Chicago. Most of the initial speculation spit out the names of Oakland president Billy Beane, Yankees general manager Brian Cashman, Rays general manager Andrew Friedman, Padres general manager Josh Byrnes, and White Sox assistant general manager Rick Hahn.
Writing for Foxsports.com in mid-September, Jon Paul Morosi captured the popular media sentiment about the possibility of Epstein joining the Cubs:
“There is only one problem with this scenario: Epstein has a contract for 2012—in Boston.
“The Red Sox are on the verge of their seventh playoff berth in Epstein’s nine seasons. The franchise is in the midst of its greatest era, in the baseball and business departments. For what possible reason would Red Sox owner John Henry—who, again, has control over Epstein’s services for one more year—allow him to break the contract and leave?”
By then, Ricketts knew he wanted Epstein. That summer, Ricketts had asked 20 people he knew in baseball—owners, executives, and agents—to recommend the best person for the job. Nineteen of them told him Theo Epstein. What the media and Ricketts didn’t know about Epstein was how much his moorings to Boston and the Red Sox had loosened over the years. They were about to reach the breaking point.
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Theo Epstein was born December 29, 1973, in New York City one minute after his fraternal twin brother, Paul, to proud parents Leslie and Ilene Epstein. Leslie told the Yale Daily News in 2002 that they decided on the name Theo because the baby was conceived in Holland, they wanted a Dutch name, it was popular at the time, and it had the added benefit of being the name of Vincent Van Gogh’s younger brother. (Theo Van Gogh was a Dutch art dealer who died at 33, six months after Vincent died at 37.)
Writing coursed through the Epstein bloodlines. Epstein’s father is a Rhodes scholar and an accomplished novelist who directed the creative writing program at Boston University. Epstein’s grandfather and great-uncle, Phillip and Julius Epstein, won the 1944 Academy Award for screenwriting for the movie Casablanca, which also won for Best Picture. Phillip Epstein died in 1952. For years his Oscar rested in the den of Theo’s parents. Theo’s sister, Anya, would become a screenwriter.
Theo’s life began on the Upper West Side of Manhattan. He lived there until 1978, when he was 4 years old, when Leslie and Ilene moved the family to Boston, not far from Fenway Park. They arrived just in time to see the Yankees’ Bucky Dent break Boston’s heart with a home run in a one-game tiebreaker. Leslie, Theo, and Paul would attend about a dozen Sox games every season at Fenway, with young Theo keeping score all nine innings. In 1984, as a fourth grader at Brookline Elementary, Epstein read for the first time Bill James’s Baseball Abstract, which explained and analyzed baseball like nothing else before—from an advanced statistical perspective. Even at age 10, Epstein knew the book changed the way he looked at baseball. The idea that one book could so deeply alter his vision of the game astounded him, and forever left him open to new ideas about a game hidebound by tradition.
Books would play an important role in shaping the future general manager. Leslie Epstein made sure that Russian novelists, Charles Dickens, William Faulkner, Ernest Hemingway, and the other great authors were as much of a part of Theo’s childhood as the Red Sox. An Epstein house rule stipulated that every minute spent watching baseball on television had to be equaled by reading books.
“A doubleheader,” Theo said, “was a lot of reading.”
The reading material, nuanced and evocative, nurtured what would become one of his greatest traits as a general manager: empathy. The seeds were already there. “Maybe,” he said, “it’s part of being a twin. I’m a twin. My mom’s a twin. My grandfather’s a twin.” He remembered what his parents would tell 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.
Cubs manager Joe Maddon, after working with him for two years, did not hesitate to define what stood out most about Epstein.
“One word: empathy,” Maddon said. “He’s brilliant, he’s sabermetrically inclined, he’s old school, he understands old-school scouting techniques, he understands the game, but of all the guys I’ve met, he’s more empathetic than all of them. He understands people. And he feels what they feel.
“When you have a conversation with him, it isn’t sterile. There’s feel. Feel is a part of his method. I don’t know whether he does it intentionally or not. I just think that’s who he is.
“What sets him apart from all the really good guys I’ve worked with is he’s more empathetic than all of them. We get involved in [analytics], but we never get involved in that 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. That’s my conclusion.”
One day, when Epstein was about 10 years old, a man who ran a summer camp came to the house. He asked Theo to make a pick among three theoretical bunks with 15 kids: one with individualists who all did their own thing, one with team players who spent every moment together, and one with a mix of all types. It was a setup to steer a child toward being around kids of all kinds, except Theo quickly took the second option.
“It sounded fun for me,” he said. “I always liked being with people I like and respect and seeing other people enjoy good times. I’m competitive, too, and that’s why baseball’s worked out for me: working shoulder to shoulder with people.”
Epstein was 12 years old when Leslie took him and Paul to Game 3 of the 1986 World Series at Fenway Park between the Red Sox and the New York Mets. New York drubbed Boston, 7–1. But six days later the twins watched on television at home as the Red Sox held a 5–3 lead in the bottom of the 10th inning of Game 6 in New York. There were two outs and nobody on base. One more out and the Red Sox would be World Series champions for the first time since 1918. Theo and Paul climbed to the top of the living room couch, ready to leap off in celebration upon the final out. It never came. The Mets rallied on three singles, a wild pitch, and an error to win, 6–5. Theo and Paul climbed down and writhed in pain on the floor. Fully indoctrinated at age 13, Theo Epstein understood the visceral pleasure and pain of what it meant to be a Red Sox fan. Welcome to the club.
Epstein attended Brookline High School, where he played soccer and baseball, contributing as a part-time player and third base coach, before he went on to Yale, where he covered sports for the Yale Daily News. As a freshman at Yale in 1992, Epstein applied for an internship with the Baltimore Orioles, a team owned by a Yale graduate, Eli Jacobs, with a president who was a graduate of Yale Law School, Larry Lucchino, and a vice president of administrative personnel who was a Yale graduate, Calvin Hill. Epstein’s application wound up on the desk of Hill, who walked it to the office of Dr. C
harles Steinberg, one of Lucchino’s top advisors. While Epstein’s friends spent spring break that year in Cancun, Epstein visited Steinberg for an interview. The Orioles hired him, and liked him so much they brought him back for two more summers.
Epstein liked writing, but what he observed in the Orioles’ press box of the life of sportswriters convinced him he wasn’t cut out for the writing life. He saw the profession as a lonely, individualistic pursuit. He watched writers who sat by themselves and worked by themselves, then retired to the hotel bar. He wanted a more collaborative life, which he saw in professional baseball.
Lucchino left Baltimore to join the ownership group of the San Diego Padres in December 1994, 16 months after Jacobs sold the Orioles at auction to a group headed by Peter Angelos. Soon Steinberg joined him. And so, too, in 1995 after graduating from Yale but still without a driver’s license at age 21, did Epstein. He began in the Padres’ public relations department, mostly assigned to entertainment projects, such as displaying birthday wishes on the scoreboard. Steinberg drove him back and forth to work every day. Epstein worked his way up to a position as public relations assistant who wrote game notes for the media. His detailed work and diligence caught the eye of Padres general manager Kevin Towers, who in 1997 moved him to the baseball operations department.
In San Diego, Epstein’s desk ostensibly made for the DMZ in the newly raging war between the few whip-smart number crunchers who were starting to fold quantitative analysis into the game and old-guard scouting and development men who were resisting the switch to analytics. His desk sat right between the team’s analytics guru and the scouting director. They couldn’t stand each other and rarely spoke to one another, but both of them enjoyed the company of Epstein.
Epstein obtained his driver’s license at 23 and soon thereafter a law degree. When an Anaheim law firm offered Epstein a starting salary of $140,000 in 1998, Towers promoted him to director of baseball operations and boosted his salary from $30,000 to $80,000. At a time when Triple Crown statistics (batting average, home runs, and runs batted in) still held sway among Major League Baseball decision makers, Epstein taught Towers about less familiar metrics that could give a more accurate assessment of a player’s value, such as OPS (On-Base Plus Slugging, the sum of on-base and slugging percentages), strikeout-to-walk ratio, and ballpark factors.