Theo in Love

Among those who’d be in a position to know, there’s some disagreement about how and where Theo Epstein has celebrated his betrothal to his fiancée, Marie Whitney. There was, to be sure, a proper engagement party, held on a Saturday night in August aboard Red Sox owner John Henry’s yacht. As to whether the groom-to-be has had a good old-fashioned bachelor party, though, things get murkier. Epstein himself, who declined to be interviewed other than to issue this denial, says no. But a few colleagues and friends of friends tell of a night out with the boys, during which dirty jokes were tossed around, beer bottles raised in toasts. At one point, the story goes, the guys started chanting, “Theo! Theo!” But the guest of honor didn’t hear them. As his buddies drank to his pending nuptials—and this is the part that really rings true—Epstein was checking in with Whitney on his cell phone.

And there you have it: classic Theo Epstein, a man with a serious commitment to true romance, privacy, and priorities. When he came back to his hometown four years ago to work for the Red Sox, and soon after became, at 28, the youngest general manager in the history of the game, the gossip columns swooned. “Just when we were getting bored by the same old hunks,” wrote the Herald’s Inside Track in November 2002, “the Red Sox throw us some fresh meat…molte grazie, Larry Lucchino!” After all, Epstein had the looks (those blue eyes! those distinctive eyebrows!), the smarts (Yale grad!), the creative streak (playing guitar in his own band!), and the sky-high salary of a major-league exec. We expected wild nights in bars and glamorous girlfriends. We were wrong.

By the time he earned his big promotion, Boston’s new Most Eligible Bachelor was in fact already off the market. Back in the spring of that year, while at Vox Populi, he had met and fallen for Whitney, a local girl with a big heart who was working on graduate studies at Harvard in healthcare policy and volunteered helping the homeless—“definitely not a stripper,” as a sportswriter close to Epstein puts it. “She’s got a social conscience, and that really appeals to him, especially compared with the girls who throw themselves at him at Fenway.” Whitney’s job at Horizons for Homeless Children—leading activities at play spaces set up in shelters—is one of the most challenging in the organization. “That’s intense work,” says Susannah Kerest, a former colleague. “It takes a patient and very loving person.” If you know a bit about Epstein’s dating history, it’s hard to imagine him winding up with anyone else.

LEARNING THE GAME

Growing up in Brookline, Theo was a gangly sports geek who preferred fielding fly balls to flirting with girls. When he was 12, he suffered a gash over his eye in a collision during a soccer game, and for years after was forced to compete in sports goggles. “Did girls like him? Kinda, sorta,” remembers former classmate Tessa Skinner, who now works at Boston University. “Some girls thought he was cute. He was this skinny kid with glasses. When he ditched the glasses later in high school, he got a little more popular.”

Even as his social standing improved, Theo spent most of his time hitting the books or playing sports. “He wasn’t a big partier,” says George Borokhov, another former classmate. “He took a lot of AP classes. He didn’t have girls around him.” Theo and his pals liked hanging out at Village Fare Pizza and shooting pool at Boston Billiards; one of their craziest hijinks, if this counts, was egging cars at Halloween. (In the 1991 Brookline High yearbook, Theo’s posse took out a page. Theo “Tom Flash” Epstein, who scored in the high 1400s on his SATs, listed this as his favorite saying: “I got into Yale early!”) When not palling around with his friends, Theo and his twin brother, Paul, would play basketball or engage in noisy one-on-one in the hallway of their family’s apartment. After one particularly loud game, a neighbor reportedly yelled, “You guys are 15 years old! You should be out drinking beer and chasing girls!”

At Yale, Epstein took that advice—in his own prudent way, of course. During his time in New Haven he fell in with a crew of party-boy hockey players who threw wild bashes and attracted a band of female groupies. “These girls were crazy—at one of our parties, some of them were pulling off their bras like in those Girls Gone Wild videos and draping them on top of some of the guys’ heads,” says a former Bulldog. But Epstein was never the rowdy one. He wasn’t a ladies’ man, not a campus stud like some of his hockey pals. “He wasn’t shy but he wasn’t the one hanging from the rafters,” says a hockey player. “He’d stand back and watch his buddies do that.”

Epstein arrived on campus as “this scrawny kid with big ears,” remembers Jack Gilden, who worked with Epstein during the future GM’s freshman-year internship with the Baltimore Orioles—a job Epstein interviewed for while his friends spent spring break in Cancún. Though he bulked up during his college years, it was Epstein’s wicked sense of humor that attracted the most attention. “Theo was very, very funny,” remembers Noah Bookbinder, who was the managing editor of the Yale Daily News, where Epstein worked as sports editor. “He could be very irreverent, coming up with inside jokes, plays on words, physical joking—he was very charismatic.” Epstein could fit in with almost anyone, brainstorming with the journalism geeks by day, partying with the hockey team by night. He dated across the spectrum. “He had some girlfriends, though I don’t think any were of long duration,” says a hockey player. “You’d see them together for a few months and then that’d be it,” says another. He didn’t share many details about his exploits, either. Most friends can’t recall Epstein’s having a serious relationship during or since college until he met Whitney. “I usually get the six-month itch, and I haven’t gotten that,” he told the Globe in December 2002 about the budding romance.

Epstein spent his senior year at Yale living with nine roommates in a house in New Haven that became known for late-night throw-downs. But to classmates who weren’t part of his inner circle, Epstein didn’t make much of an impression. Many of his neighbors at Jonathan Edwards College hardly remember him, and Epstein is missing from the group shots of both his dorm and the newspaper editorial staff in the yearbook for Yale’s Class of 1995.

GETTING TO SECOND BASE

After Epstein graduated from Yale, he went to work for the San Diego Padres. But though he was a single man about town, living in the city’s hip Pacific Beach neighborhood, he was too busy building his career to spend much time pursuing a love life. The consummate workaholic, Epstein earned a law degree at the University of San Diego while putting in 70 hours a week for the Padres. “He was not super social,” remembers classmate Amber Spataro. “Every Thursday night we’d hang out at a local bar, but Theo kept to himself.” Not that he would have impressed too many ladies. Not only did Epstein lack the requisite shiny sports car—he didn’t even know how to drive when he first arrived in San Diego. “He lived close to Qualcomm Stadium, so he would either walk to work or people would pick him up,” says Washington Nationals baseball information director, John Dever, who used to work in the Padres’ press office.

That workaholic streak has followed Epstein to Boston. Whenever he finds himself in a situation that could lead to some mischief-making, he always makes the safe, if boring, choice. A couple of years ago, when Epstein and six other Red Sox staffers rented a house with a Jacuzzi and plenty of bedrooms near Fort Myers during spring training, it had all the makings of a permanent frat party. But it was more Full House than Animal House. “It was actually very laid-back,” says one Sox staffer who lived there. “During the day we’d be on the field, and at night we’d hang out and watch TV. Some of the guys had their wives or girlfriends come visit. And that was about it.” In 2003, Epstein tiptoed tantalizingly close to producing some scandalous headlines when he agreed to an interview with Playboy, on the condition that the magazine let his Red Sox posse throw a party at the Playboy mansion. But work intervened as the team’s hectic winter meetings took priority, and Epstein squashed the idea, to the chagrin of not a few of the guys.

HEADING FOR HOME

For all the local press’s drooling over the “hunky,” “baby-faced,” and “ever eligible” Epstein, his romantic life has remained a big fat mystery. And that’s just the way he likes it. When reports first linked Epstein to Whitney, he would reveal only her age (she turned 28 in September) and occupation. Soon after the engagement was announced, Whitney was flashing her diamond ring during a Yankees game, but Epstein has kept mum about the wedding. (His friends help protect that privacy—during the reporting for this article, his pals were stingier with details than paranoid CIA agents.) While we hear ad nauseam about his jam sessions with Eddie Vedder or red carpet adventures with Ben Affleck, the only hints that Whitney even exists are occasional sightings of the pair dining at Stella, skiing in British Columbia, shopping at Wal-Mart in Fort Myers.

This we know: Though he was hesitant at first, friends say Epstein likes to serenade Whitney on his guitar, strumming some of his favorite songs by the White Stripes, Neil Young, and, naturally, Pearl Jam. He walks her dog on the weekends to let her sleep in late. On the night in May when he popped the question, the two had dinner at Davio’s, where he managed to avoid tipping off the restaurant’s staff that anything special was afoot. “They were just like any other couple out for dinner,” says waiter Robert Mahon. “She ordered for both of them. There was no champagne toast; I don’t think she even drank! He had a vodka cocktail and that was it. When we read about the engagement in the papers, we were all a little surprised.”

Even his coworkers in the Sox front office don’t know much about Epstein’s private life; most couldn’t say for sure whether he keeps a photo of his fiancée on his desk. “He rarely talks about Marie,” says a colleague on the team. “But we tease him because whenever he’s on the phone with her, he lowers his voice to a soft whisper.” It’s unlikely he’s filling her in on his free-agent strategy, though you never know: “At first, Marie could barely tell a ball from a strike, and now you hear her talk about the ‘merits’ of particular players,” another colleague says. Epstein’s former assistant, Arizona Diamondbacks GM Josh Byrnes, says Epstein makes it a priority to get away from work and spend time with Whitney and his family. “I don’t know if she likes the game,” says Byrnes. “Some people in baseball, their wives like the game. But he’s happy and that’s important.”

Though the big day isn’t until next August (so they say), the couple have already done the customary registry shopping, creating fairly uninspired wish lists at Williams-Sonoma, Crate & Barrel, and Pottery Barn; along with items that seem to indicate Whitney plays the manager in their operation (a flour sifter, a set of cute embroidered napkins), the one vaguely indulgent request is a crème brûlée torch set. Naturally, the two are doing their best to keep the planning under wraps, and even most of Epstein’s friends and colleagues are in the dark about the details of the nuptials. You can bet we’ll fill you in, just as soon as our invitation arrives.