He really should be enjoying this. On an early November day when Boston is setting a record low temperature of 25 degrees, Theo Epstein is in 82-degree Key Biscayne, Florida, staying at the Ritz-Carlton. But throughout the week, he seldom steps outside the elegant beachfront hotel with a staff so well trained that bellmen address arriving guests by name even before they’ve stepped out of their taxis.
At one point, before making his way onto an elevator during a typically hectic day, Epstein steals a glimpse through the window of swaying palm trees. “Man, it’s beautiful out there,” he says. “They should save everyone some money and hold this thing at the O’Hare Hilton.”
This thing is Major League Baseball’s annual general managers’ meetings. And this year, it would make sense that the architect of the curse-smashing, history-defying, World Series winning Red Sox would be the star of the show. He is, to a certain extent. Any time Epstein runs into his counterparts from other clubs, they congratulate him. He says things like “I really appreciate that. But it’s all about the players. The guys really played their asses off.”
During the opening meeting, as per tradition, the GMs from the league’s 29 other clubs treat Epstein to the round of applause accorded the executive from the championship team. Also following tradition, he treats the other GMs to the first round of drinks. This being the Ritz, that tab tops $400.
Yet there is evidence that the fraternity of baseball executives still doesn’t quite know what to make of Young Theo. Sure, he is no longer discounted as the untested, stats-obsessed kid with a laptop that he was two years ago, when, at 28, he became the youngest GM in the history of the game. But he has yet to be fully embraced by an establishment still dominated by men who have logged decades sitting on wooden benches in crappy ballparks. He is not like them, not only because of his youth but also because he enjoys a public following and first-name recognition that rival his star players’. Maybe this helps explain why, when the award for Executive of the Year is announced - an honor the GMs bestow on one of their own - Epstein doesn’t even garner enough votes to crack the top three.
The ballots break differently when it comes to the Globe Magazine’s “Bostonian of the Year” honor. True, baseball is only a game. But it’s impossible to name an achievement in the past year that brought as much universal and unifying joy to New England as the long, long overdue Red Sox triumph. Many deserve credit, but one man coolly remade the team, then guided it with boldness and backbone. That Epstein, in just his second year on the job, succeeded where his more seasoned predecessors over eight decades had failed only makes the accomplishment more remarkable.
Outside of the GM fraternity, Epstein gets more attention than he’d like these days, and that’s despite his insistence on turning down million-dollar book deals and repeated requests to bring his good looks and local-boy-made-good story to Leno, Conan, and Kimmel. Jed Hoyer, one of Epstein’s deputies, marvels at his boss’s resolve. “As high as his stature is, if he wanted to, it could be so much higher,” Hoyer says. “It would be very easy for him to really cash in.” Epstein says he’s uncomfortable being singled out for a team effort and unwilling to surrender his privacy. Hoyer offers an additional reason: “Theo knows that baseball is a business that can humble you in a hurry.”
Seeing the Red Sox win the series brought Epstein incalculable joy. And relief. “Best feeling I’ve ever had” is how he puts it. He smiles broadly as he recalls the bus ride the team took from Logan to Fenway the morning after beating St. Louis, how people hopped out of their cars on the highway and stood waving and hugging one another. “It was the first time it really struck us how directly this was going to be shared, by the whole city, the whole region,” he says. “It was incredible.”
While New England continues to bask in the afterglow, with commuters still accessorizing their Brooks Brothers suits with BoSox caps, Epstein has moved on. In fact, he can’t get there fast enough. He’s determined to avoid the complacency that can be as much a part of the worldchampionship package as the giant trophy.
Bask too long, and he risks being forced to confront the question hanging unmistakably in the air: What do you do when your wildest professional dream has come true - and you’re only 30?
Bask too long, and the man who helped bring historic happiness to Red Sox Nation by assembling this year’s lovable, series-grabbing squad might somehow lose the resolve to do what he knows may be necessary if the team is to be more than a one-hit wonder: dismantle this year’s lovable, series-grabbing squad.
“There’s no room for sentiment,” he says.
The Epstein family has grown accustomed to the steady demands from complete strangers looking for a piece of Theo - the requests for tickets, for Theo to speak at their son’s bar mitzvah, for Theo to go out with their daughter or sister or friend. But each family member realized at different times how outsized his impact is on the region. For his fraternal twin brother, Paul, it was riding with him on a duck boat as it rolled through Boston during the victory parade and hearing countless fans cheer Theo’s name. For his mother, Ilene, it was seeing the stream of women march their sons into the Studio, the tucked-away clothing boutique she co-owns in Brookline’s Coolidge Corner, so they could “meet Theo’s mom.”
But for his father, Leslie, the dawning happened back in the spring, as he was walking along Beacon Street late one night. Through the open door of a bar near Fenway Park, he spied seven or eight old guys on their stools, seeming alone in the world, united only in their devotion to the Sox. “Suddenly, it came to me,” Leslie recalls. “Theo’s intelligence and judgment would, in part, determine whether these lonely guys were going to be happy this year. They’ve been so disappointed in the past. I thought, `Oh, my God, does Theo have a lot on his shoulders.’“
In some ways, his father can blame himself for that. Theo was born in New York and may have well grown up a Yankees fan had Leslie not taught him to loathe the pin stripes as a team for “bankers and bullies.” Cheering the underdog Sox became a family passion when Theo and Paul were 4 and their sister, Anya, was 8. It was the Year of Bucky Dent, and the family moved from the Upper West Side to Brookline so Leslie could join the faculty of Boston University. The Epsteins bought a condo less than a mile from Fenway. Theo accompanied his family to many games, and he quickly became the most intense fan.
But his baseball career didn’t begin until after his freshman year at Yale, when he scored an internship with the Baltimore Orioles. He impressed Larry Lucchino, the current Red Sox CEO, who ran the Orioles at the time. After Epstein graduated as an American studies major in 1995, he took a low-level media relations job with the San Diego Padres, the team Lucchino had recently taken over. Epstein then climbed the ranks of baseball operations, soaking up knowledge from Padres GM Kevin Towers. Meanwhile, he earned his law degree from the University of San Diego, an investment that continues to pay dividends when he negotiates contracts.
More important, it was in San Diego - 3,000 miles away from Boston, working for a small-market, National League team in a city where baseball is outshone by any number of diversions, including a zoo, for crying out loud - that Epstein learned to divorce himself from the passions of the grandstands.
“I am no longer a fan,” he says now. “I am no longer that kid who was rooting for the Red Sox, and thank God! Because if I were, it would be impossible for me to do my job.”
When Lucchino came to Boston in 2002 as part of the new Sox ownership group, Epstein eagerly accepted the job of assistant general manager. But he was more apprehensive in saying yes later that year, when Lucchino offered him the GM position after his first choice, Oakland’s Billy Beane, backed out. Lucchino says that after surveying the remaining field, “it struck me that Theo had a much higher ceiling and a much greater probability of success.” But Epstein worried about the pressure and the stakes.
As soon as his promotion was announced around Thanksgiving, media everywhere latched onto his youngest-ever story. It was the first time the late-night TV shows came calling. “I haven’t accomplished anything yet,” he said, declining the offers. So instead of sitting on the Tonight Show couch, he watched from home as Jay Leno joked that the new Red Sox GM was last seen being dangled over a balcony by Michael Jackson.
The media attention also caused the first strains between Theo and his family. The Epsteins are a warm, vibrant bunch. And successful. Theo’s grandfather and great-uncle, Philip and Julius Epstein, were the Oscar-winning screenwriters of Casablanca. His father is an accomplished novelist and longtime director of Boston University’s creative writing program. His mother is a respected businesswoman. His sister is a television writer who worked on the critically acclaimed NBC show Homicide: Life on the Street. And his brother may have the most profound, if least publicized, impact in his job as a social worker at Brookline High School, where he and Theo graduated in 1991.
Yet no one in the family was ready for the commotion that Theo’s ascension on Yawkey Way would cause. Leslie and Ilene proudly opened their home to reporters and TV crews. “My parents showed pictures of me as a naked baby and others from that awkward phase as a kid, which for me lasted from 6 to like 20!” Theo says. “It was important to me when I first got the job, and I was 28, to be taken seriously on the merits, and not as a novelty item.”
So, he says, “I laid down a rule with my parents that they don’t talk to the press without clearing it with me.”
Asked if it was tough to tell his parents what they could and couldn’t do, Theo smiles. “Actually, after you’ve seen your mom showing your naked butt on TV, it’s pretty easy to do that.”
Theo was working so many hours that he seldom had time to see his family. Even when he did, it was hardly the baseball-free zone that he craved, since the Epsteins have long been the kind of hard-core fans who keep sports radio playing in the background. “They’d say, `Well, Ray from Lynn said this.’ And I’d be like, `You’ve got to be kidding me! I don’t want to think of you guys sitting there listening to this stuff.’“
The family worked through those tensions, and remains extremely close. Paul and Theo continue to talk just about every day, a habit the twins started as freshmen in college when they were living apart for the first time.
His family says Theo’s girlfriend is a critical presence in his life. Though he zealously guards his privacy around this relationship, he will say this much: She is a 26-year-old who worked in the biotech world and is now in graduate school for healthcare policy. He’s also happy to point out that they began dating before he became GM, having met in the spring of 2002 at the Back Bay restaurant Vox Populi. She’s only a casual fan of baseball, so he loves the fact that they can go weeks at a time without discussing the game.
He’d been living in a bunker for weeks, depriving himself of much in the way of sleep or contact with the outside world as he and his deputies tried to hatch a trade that would right their underperforming team. Just minutes before the trading deadline on July 31, and just an hour after he had told principal club owner John Henry that he was pretty sure no swap would materialize in time, Theo Epstein had pulled the trigger on one of the most audacious trades in team history.
After the 4 p.m. deadline had passed, and after being reassured by his deputies that he had been right to unload face-of-the-franchise Nomar Garciaparra for a pair of comparative unknowns - Orlando Cabrera and Doug Mientkiewicz - Epstein walked out of his Fenway office. As he began making his way to the TV cameras, his cellphone rang. It was Paul.
“What happened?” his brother asked.
“What do you mean?” Theo responded.
“That’s all you guys got for Nomar?”
“Paul, these are good players. This is a really good trade.”
“Well, I’m listening to talk radio now.”
Normally, Theo says, he has no interest in hearing about the chatter on WEEI. This time was different. “All right, what are they saying?”
“You’re getting killed. People are furious that Nomar was traded for a couple of .240 hitters.”
Nobody says that anymore. If anything, the prevailing view on talk radio now is that the Nomar trade saved the season.
Epstein doesn’t buy that either: “Anyone who points to a direct causal relationship between that trade and our turnaround is missing the boat.” He says it was a combination of factors, precipitated by the hard-fought July 24 showdown with the Yankees. He also gives enormous credit to manager Terry Francona, with whom he had some tense conversations earlier that month when the season seemed to be slipping away.
But here’s what you can safely say about the Nomar trade: It fundamentally changed Epstein’s tenure as GM.
During the post-trade news conference, Epstein explained that he made the move to improve the team’s poor defense, a flaw for which he took responsibility. Only after he headed back to his office did reality begin to set in. All his assistants had gone home. The flat-screen TV on the wall was tuned to ESPN, which was showing a picture of Nomar in a Cubs hat. “It hit me for the first time, emotionally, that there would be real consequences to the organization and to me personally if it didn’t work out,” he says.
Later, he dialed up John Henry and told him, “It was the right trade, but no one likes it.”
Henry responded, “You must feel like the loneliest man in America.”
Epstein watched as Boston lost to Minnesota, with Cabrera, Nomar’s replacement at shortstop, making the error that gave the Twins the go-ahead run. Epstein’s self-doubt began to swell: Did I just make the worst trade in baseball history?
That night, his mind would not stop racing. His girlfriend gave him a sleeping pill - the first he had ever taken. The next morning, he resorted to mental tricks to keep his confidence up, reminding himself that many other people in the world were confronting far more serious challenges.
Over the next few weeks, he checked the Cubs box scores faithfully, noticing that Nomar was playing well while Cabrera struggled at the plate. At one point, Epstein’s internal conversation went like this: “If the nightmare scenario comes true, and Nomar plays well, and the Cubs get into the playoffs and we don’t, this is going to be a serious roadblock. It could potentially ruin my tenure here.”
Ownership expressed confidence in him, but there was no denying that if the trade went bad, that whole “youngest GM in baseball history” moniker would be quickly forgotten. Ditto for all of Epstein’s earlier magical maneuvers, such as scooping up an undervalued gem like David Ortiz, signing closer Keith Foulke, or spending a Thanksgiving with Curt Schilling’s family, persuading the skeptical right-hander to come to Boston. Epstein would simply be remembered as the guy who made the worst Red Sox deal since Harry Frazee sent the Babe packing.
Still, a hallmark of Epstein’s approach is his refusal to panic. Even in this dark period, he continued to remind himself that he had made the trade for the right reasons. Within a few weeks, Cabrera became a hitting spark plug, and the Sox became the hottest team in baseball. And Epstein started sleeping better.
ON THE FRIDAY BEFORE he will leave for the GM meetings in Key Biscayne, Epstein is sitting in his sparsely decorated office in the basement area of Fenway where a bowling alley used to be. He is unshaven and wearing an untucked pale-green oxford shirt, jeans, and black Adidas sneakers. Around him is a bottle of 2004 World Champions Champagne, his acoustic guitar, a framed picture of his niece, and a framed-but-not-yet-hung double platinum album signed by Pearl Jam’s Eddie Vedder.
Just after 6 p.m., Epstein calls through his office window, “Is Jean still here?”
An aide, Brian O’Halloran, looks toward the other end of the baseball operations office, where administrative assistant Jean MacDougall usually sits. “No, she’s gone,” he says.
“OK, it’s time for tape ball,” Epstein says. He walks into the outer office, holds his palm out, and a softball-shaped mass of scrap paper and Scotch tape comes gliding to him. He winds up and hurls it clear across the office. Whoooosh! It sails. Thwaapp! It smacks the wall. Someone grabs a Wiffle ball bat and begins hitting his pitches.
Epstein hands the ball to Josh Byrnes, his assistant GM, who, at 34, is the oldest of the 10 or so staffers in the office at this moment. Byrnes launches a pitch that goes high and smacks into a framed Fenway print on the back wall. Glass shatters. The consensus: Jean is not going to be happy. The veteran employee, whose desk is near “home plate,” may not go for these mild frat-house antics, but Epstein believes releasing steam is essential to sustaining the front office’s insane hours. “It’s fun because it has to be.” The staff, composed largely of young guys with degrees from elite colleges, seems to agree.
There are lots of laughs to go with the long days. Epstein is a good impressionist and can enliven even the dullest contract discussion by assuming the voice of “Borat,” the hilarious Kazakh character from HBO’s DaAli G Show.
Epstein prides himself on having good relations with the Red Sox players, but he is careful to keep a professional distance. If he bumps into them at a bar, he says, he’ll buy them one drink and then make his exit. He is particularly comfortable with certain players, such as Kevin Millar. One recent Friday night, Epstein was lying in his bed flipping through the channels when he stumbled onto Millar peddling team-signed bats on the QVC shopping network. He immediately left a mocking message on Millar’s cellphone. After the show ended at 1 a.m., Millar returned the call. “I was hoping no one would see it,” Millar said later. “He gave me a red flag for being on it, but I gave him a red flag for watching.”
Millar, who delighted in ribbing Epstein after the New York Daily News put his picture under the headline “Revenge of the Nerd,” says he loves having a friendly relationship with his GM. Yet he also knows that if Epstein thought he could improve the team by trading him, he’d do it. “I know Theo likes me and what I bring to the club,” Millar says. “But there’s also a business side you need to separate. Players might not like it, but they understand it.”
The two words used most often to describe Epstein are “poised” and “prepared.” The former flows from the latter. All this preparation doesn’t inoculate him against mistakes. This is, after all, the guy who signed washout Byung-Hyun Kim to a $10 million contract. It just helps Epstein improve his odds.
The stresses of the job never really let up. On game days, Theo & Co. tend to work from morning until midnight. But every season has its own pressing demands: hatching trades and free-agent signings; battling over contracts and arbitration; bulking up and then whittling down the roster; preparing for the draft and mid-season trading deadline; evaluating minor-league talent and developing the farm system; and doing advance scouting during the playoffs.
When they get to the Key Biscayne Ritz, Epstein and three of his deputies - Byrnes, Jed Hoyer, and Peter Woodfork - set up shop in Suite 627. Throughout the week, representatives of the various clubs visit one another in their suites, trying to sniff out possible trades.
This free agency period is particularly tricky for Epstein, since it began with 16 members of the championship squad - notably Jason Varitek, Pedro Martinez, Derek Lowe, and Cabrera - up for grabs. As much as he would like to keep the team together, he says economic realities make that impossible. “We’ll lose some players as other teams will make them offers that simply don’t make sense to us.”
Some baseball veterans have faulted Epstein for worshiping at the altar of sabermetrics - the mathematical study of baseball - rather than relying on more traditional factors like the eyes and guts of longtime scouts. In reality, though, Epstein craves information from objective and subjective sources. He listens closely to both his statistician guru, Bill James, and his 70-year-old special assistant, Bill Lajoie, a trusted scout who was GM of the 1984 World Series champion Detroit Tigers. As Epstein navigates his way through this off-season, he keeps going back to something Lajoie said on the night the Red Sox made history in St. Louis. “Teams make very bad decisions after they win a World Series,” Lajoie said. “They get a little bit sentimental. They think a million here, a million there, an extra year for this player here, an extra year there. They want to hold on to what happened in the past. But you can’t.”
And so the hunt goes on. Epstein and his aides spend hour upon hour strategizing in their suite. When Epstein is particularly deep in thought, he tips his head at exaggerated angles, like a swimmer trying to get water out of his ears.
At one point, he stands in front of a flip chart, summarizing their progress in preparation for a conference call he will hold with the ownership group: Henry, Lucchino, and Sox chairman Tom Werner. (The Globe’s corporate parent, the New York Times Co., holds a 17 percent interest in the franchise.)
Some matters remain out of Epstein’s control. On Tuesday evening, despite several attempts to reach out to agent Scott Boras about Varitek’s contract, Epstein has not heard back. Yet earlier in the day, Boras had given an interview to WEEI. So Hoyer calls up an audio file from WEEI’s website. Epstein sits on the couch, staring alternately at the ceiling and at Hoyer’s laptop, listening to Boras make his demands over the airwaves.
This is not how Epstein likes to negotiate. Especially since Boras, at that very moment, is staying in his own suite, which happens to be a few doors down from Epstein’s on the same floor of the Ritz.
IN THE WEEKS SINCE THE WIN, a grateful RedSox Nation has gone out of its way to give Theo its thanks. He appreciates that but recoils from the intensified demands to be a celebrity. “That’s just not how he is built,” says his father. “I’ve seen him pull his hood over his head in an airport. When people wave to him from across the street, he’ll wave back. But I see him wincing.”
Despite his youth (he will turn 31 in a few days), Epstein realizes he has already given up a lot in his all-consuming drive to bring a championship to Boston. But his father says, “He shouldn’t regret anything. My God, he’s made so many people happy. That should be the goal of all of us in life.”
For such a goal-oriented person, what’s next?
Well, you won’t see him cash in by popping out one of those obligatory bestsellers offering the secrets of his success. For someone who deftly manages a $130 million payroll, Epstein seems remarkably uninterested in money in his own life. He is in the final year of a three-year contract that makes him one of the lowest-paid GMs in the game. He knows that will change when he negotiates his next contract, but his salary doesn’t appear to be a chief concern right now. Aside from using some of his cash to buy a condo, he chooses to keep his money in a basic savings account and forget about it.
How about a political future? Don’t count on it. Lajoie has told Epstein to get out of baseball after 10 years and run for senator and then president. “That’s what I see in this man.” Yet Leslie Epstein says Theo recently told him he has no interest in politics. That may surprise people who saw him stump for John Kerry in New Hampshire. But Epstein says that as strongly as he opposes the Bush administration, he was reluctant to mix baseball and politics. He agreed to speak out for Kerry only after seeing Schilling, during a live interview on Good Morning America, urge people to vote for Bush. (Both he and Schilling say the political divide in no way strained their friendship.)
So what does Epstein see himself doing down the road? He admits he doesn’t want to be a GM forever. Eventually, he’d like to settle down and have a family, which is hard to picture right now. “There is no way a human being can physically maintain the work schedule and pace that Theo sets for himself,” says John Henry. And, as much as baseball is at his core, he hopes someday to have an impact outside the game, something he sees his brother doing by improving the lives of the students he works with. “There are a lot of people suffering,” he says. “My brother does something about it every day, and I don’t. But I certainly will at some point.”
Before that, though, he’s got a lot more suffering he wants to relieve in Sox fans. “Everyone talks about 1918, and they talk about it as the last time the Red Sox won the World Series and started the curse,” Epstein says. “I look at it as the end of the first era of Red Sox dominance. They won five World Series from 1903 to 1918. They were a dynasty, and they set a standard for excellence in the game. It would be terrific if we could get back to that.”
In the end, Young Theo is determined to have done exactly that by the time he nears middle age. That’s why he refuses to get emotionally attached to this year’s roster.
What do you think, Nation? After seeing him do the impossible in just two years, do you trust him enough to believe he’ll deliver you a dynasty? Enough to forgive him for what he’s about to do?