But as his own school career faltered, Chambers advised Ed Crespo to pursue a scholarship he had won at the Longmeadow High School, outside Springfield, Massachusetts. Crespo, who had trouble adjusting, attributes his eventual success to Chambers's unwavering encouragement.
The summer after his sophomore year, Chambers began working as a messenger for Davis Polk & Wardwell, a blue-chip law firm. Richard Nolan, a partner whose sons knew Chambers from Saint David's and the Greys, recalls that he did a "fine job." Back at school that fall, however, Chambers slipped into a familiar pattern. A classmate recalls the boy who "occasionally drank beer" actually strolling to the park with mixed drinks in a paper cup. Friends remember him being constantly stoned, affecting an I-don't-give-a-damn-about-anything attitude.
But Chambers's indifference may have been a pose. He confided wild schemes for making money to one friend and told another just last summer that his mother was a doctor. In fact, she was working as a nurse—twelve hours a day, six days a week, for the Hammersteins and the Hearsts, the kinds of prominent families whose children Chambers was expected to befriend. Indeed, sources close to the prosecution believe that Chambers's troubles may stem, in part, from his mother's efforts to push him into a rarefied world in which he either couldn't make it or didn't want to. It was at her urging, friends say, that he served in the Greys, in his church, and on the committee of the Gold and Silver Ball, a charity event patronized by many members of the private-school social scene.
"He didn't like the kids in the scene, but I think he was jealous of them," says one friend. "He wanted to have as much money as they did, to come back in twenty years and show them. He wanted power, a place in society."
If you'd met him, you would have liked him, says his York headmaster.
Chambers's tall good looks—he's six four and about 220 pounds—and secretive manner made him something of a legend among the younger private-school girls. A friend recalls that girls from surrounding schools used to camp out on the steps of the brownstone where he lived. He hated to be pursued that way, the friend says, and in fact, Chambers was always more comfortable hanging out with his male friends. Still, there was a sensitive side to him that he revealed to girls he liked. He also had a hard time letting go of old girlfriends. The girl who broke up with him while he was at Choate says that years later he was still pursuing her. And when Flanagan started dating one of Chambers's former girlfriends, Chambers avoided him for a year.
By the middle of Chambers's junior year, the club scene was rapidly expanding. Baird Jones had left Studio 54 the year before, and the club had enlisted Flanagan and several friends—later called the Committee—to carry on the weekend-party tradition. They were given their own private room, an open bar, and carte blanche invitations for their friends. Once, when one of the committee members couldn't get back from his boarding school for a Friday-night party he'd helped organize, the club sent a limousine to fetch him at his dormitory.
Flanagan's friend Nick Beavers, whose family later opened the Surf Club and the Zulu Lounge, provided a similar service for nearby Xenon. In fact, a number of new clubs and bars were welcoming the young students—among them, a cheerful five-foot-seven freshman at the Baldwin School, Jennifer Levin.
Levin had moved to the city from Port Washington, Long Island, earlier that year to live with her father, a successful SoHo realtor, and stepmother in their SoHo loft. She made friends easily and began making the rounds of the clubs. "She was a really cute girl—fun, happy-go-lucky," recalls Brock Pernice, who met her when he was a freshman at York. "She loved the club scene, and she was very innocent. I took her to a Billy Idol concert on our first date, but it wasn't until weeks later that I first kissed her, at the Peppermint Lounge, and then I couldn't leave her."
By the beginning of 1983, Chambers had begun to drift away from his old Saint David's and Browning friends and to hang out with a group from York known to be heavily involved with drugs. At the same time, his oldest and closest friend, John Tulenko, had become fed up with the self-destructive life that he and Chambers—and many of their friends—had been sharing. "I just realized it was a dead end," Tulenko says, "that I was only hurting myself and my parents. One night, a group of us were hanging out at this bar on East 85th Street. I remember thinking how pathetic the conversation was. We were just joking around in this cynical manner we have, but I'd stopped drinking a few weeks before and I couldn't relate to it at all. I stood up and told them to go to hell and walked out.