My college counselor, Marion Finsbury, was blunt and austere. She told me she really could not be the slightest bit encouraging about my chances of getting into Harvard, Yale, or Princeton. Or into any school in the Ivy League, for that matter. Or into Williams, Amherst, or Stanford. (Don’t bother to apply, she said.) Schools such as Duke, Northwestern, Cornell, and Penn were more my style, she suggested (yes, the latter two are in the Ivy League, but please). I applied to HYP anyway, and, as Finsbury predicted, I did not get in.
I did get into the schools she said I would—I think they made calls in those days to bolster the written applications—and I decided to go to Duke. It was a stunningly beautiful campus, with a handsome student body in bucolic Durham, North Carolina. It could not have been more different from Andover. It was a warm spring day when I visited the campus, from the northern Massachusetts tundra; the sights, sounds, and smells of the American South were intoxicating. I was ready for a geographic and ideological change. It seemed right. Still, I felt like a total failure; that somehow I had not fulfilled my mandate, or my destiny, by going to Duke instead of Harvard. Not only did I feel great disappointment deep in my core, but the ghosts of Andover made me feel like a loser, too. I was meant to go to Harvard and it hadn’t happened.
The truth was, I was more devoted to the Phillipian and my other extracurricular activities than to my studies. I was also co-head of the Jewish Student Union, a cheerleader, a radio DJ, and an assistant of some kind in the athletic department. I was very good at my job as the paper’s business manager. We made more money that year than ever before. We gave half of what we made—thousands of dollars—back to the school, another 25 percent to the school’s two-hundredth-anniversary $50 million fund-raising campaign, and split the last quarter of our profits among the board members. I think we each walked off with something like $500, a not-insignificant amount in those days.
I believed a nice celebratory dinner was very much in order. I gave Fred Stott—by then the secretary of the academy and the person in the administration with whom I worked closely to make sure our bills got paid and our revenues were properly accounted for—a heads-up that I wanted to have a special dinner for the board the evening before we were meant to hand over the reins to the paper in a ceremony presided over by Headmaster Sizer. I remember he went to the shelf in his office in George Washington Hall and pulled down an ancient tome. Somewhere in its pages was a general directive that when the school’s trustees visited the campus, they were to be provided with “adequate but not excessive” accommodation and entertainment. “Keep that in mind,” Stott told me. But in my mind, “adequate but not excessive” could mean almost anything. So I decided we would celebrate at Locke-Ober, once upon a time the most expensive restaurant in downtown Boston. I reserved a private room, with an open bar, and arranged to pay for our meal with a check drawn on the Phillipian account. The fifteen or so members of the outgoing board showed up on time, and in some form of respectable attire. We ate and drank to our hearts’ content. Anything anyone wanted, and as much again, was provided. At the end of the evening, I wrote out a check to the restaurant for something like $1,250.
By the time I showed up at Headmaster Sizer’s house the next morning, nursing a considerable hangover (I am certain I was not alone in my condition), the meal at Locke-Ober had already become legendary. Sizer pulled me aside. “I heard you had quite the dinner last night,” he said. I was shocked. How in the world had Sizer already heard about it? I’ll never know. To his credit, though, he never pressed charges for what clearly was an evening of heavy off-campus drinking, although probably I was the only one under eighteen and drinking illegally.
The way Sizer handled our Locke-Ober celebration has always impressed me. It also further drove home the point that Andover was the kind of place that celebrated performance art and encouraged quirkiness and out-of-the-box thinking. That’s an idea that had also occurred to Joshua Rothman, a culture editor at The New Yorker, who graduated from Exeter and then Princeton. One of his classmates at Princeton was Shamus Khan, who graduated from St. Paul’s and wrote Privilege: The Making of an Adolescent Elite at St. Paul’s School. Rothman credits Khan with articulating how prep schools have changed over the years to be slightly less elite but still manage to prepare their graduates with exceptional real-world navigational skills. “It’s about negotiating a relationship with the people who are older and younger than you are,” Rothman said. “The way that our elite world is now, that’s actually not a relationship of straightforward admiration and emulation. It’s actually like rebellion and skepticism and resistance are part of what’s expected of younger people but in a certain way that is productive and understood to be sort of creatively destructive or that’s to their credit. There’s a certain way of relating to people who are older than you. We’re supposed to admire those people but also critique them.” It gets even more complicated, he suggested. “There’s all these complexities around your place in the world, like you’re supposed to be pretty ironic and self-aware about your own privilege,” he continued. “You’re supposed to be pretty critical of your betters and people who are older than you. But you’re also supposed to be modifying institutions instead of rejecting them and you’re supposed to be cool and have youth culture, but you’re supposed to have the right amount of youth culture.… It’s not something that just comes naturally. It’s something you have to be immersed in, an environment where you see it modeled for you by older kids and you see it modeled by all these teachers, on what they expect and what they reward.”
Rothman believed that, as was the case with Khan’s experience at St. Paul’s, Exeter taught him—as Andover had taught me—how to strike the right balance between irony and respect, and taught him invaluable social skills. “It gives you this tool kit that allows you to wiggle your way into a space in the preexisting institutional hierarchy that you encounter as you get older,” he said. “That involves a certain amount of antagonism as well as receptivity to what’s above you.… It’s all about little ways of creating a sort of environment of trust in which you can practice all that stuff until you get it exactly right.” He observed that a poor kid at a regular high school who acts up in class is more likely to get into trouble than a kid at Andover or Exeter who is rambunctious. “It’s like a theater,” he said of the elite prep schools, “and you’re performing and everyone is getting their performance critiqued. It’s much more of a sort of safe space to learn exactly how much you can be a jerk and exactly how much you should be kowtowing to the people who have power.”
That’s what we both learned of a lasting nature during our years at Andover and Exeter. “I didn’t really learn much materially,” he said. “I took Latin and I don’t remember any of it. I remember getting to college and taking my first college-level history courses and I got my ass kicked by those classes. I thought going into them that I knew stuff. But I didn’t know anything. What I did know was how to talk really well in class, how to take criticism, how to interact, how to go a professor’s office hours—that was something I knew how to do that none of my peers knew how to do—all these skills about how to negotiate the learning environment. I was under the impression when I was at boarding school that I was working incredibly hard and that we were the Delta Force of high school students. But then one thing I discovered when I got to Princeton was that that wasn’t really true. I mean everyone else from public high school also worked their asses off, and they’d all been working like maniacs. It’s just that they didn’t have this sort of esprit de corps idea that we were all destined for great things and we were the elite squadron.”
He met his future wife at Princeton. She graduated from a public high school. “She pulled all the same all-nighters and had all the same crazy stuff that we did,” Rothman continued. “It’s just that she didn’t have a whole environment that was creating a sense of manifest destiny around that. It’s not that I learned study skills, it’s that I learned social skills.” Contrasting his professi
onal experiences with those of his wife’s puts his understanding of his years at Exeter into sharper focus. “I’m dramatically more comfortable than she is with navigating hierarchies and working with older people, and representing myself to people who are outside of my intimate circle,” he said. “It’s like I emerged sort of like a politician in a way that she did not from her high school. She emerged a worker bee and had to learn how to navigate. She worked at McKinsey for a while. She had to learn how to navigate that. Whereas I know if I worked at McKinsey, I would know exactly how to act with partners and with everyone. That would be just what I had done for my whole life when I was a teenager. One thing that always blows my mind, and which fascinates me, is when I contrast her experience of high school to mine, it’s like two data points. Her experience of high school was like Lord of the Flies. It was all about other kids her age. She had all these clubs and all these study groups that she went to. She would leave for school at seven in the morning and she would come home at night and her parents would just see her right before bed. It was really not a parental time. There was all this stuff about getting away, having secret parties in some kid’s house where the parents were on vacation. It really wasn’t like this development of a childhood adolescent world. I would have thought that boarding school was like that but it wasn’t. It was heavily oriented around adults. There was constant adult stuff. It was just everywhere. Things having to do with being observed by grown-ups and having that whole social life with them. If I think about the number of adults that I had friendly relationships with at boarding school versus the number of adults she had friendly relationships with in the regular public high school, just because of living at the school I had more intimate relationships with grown-ups than she did. I really think that’s a huge part of it.”
When I think of Andover, I like to think of that kind of tolerance for zany behavior, that idea that elite prep schools were like “a theater,” in Rothman’s articulation. Rothman’s metaphor of the Delta Force also resonates with me. It was not literally true, of course—Andover was not training anyone for military special ops. The George H. W. Bush types at Andover were far and few between, even accounting for the unusual circumstances at the time of his graduation. But the idea that we, at Andover, were special—la crème de la crème de la jeunesse américaine, after all—whether we were or not, and that much was expected of us, whether it was possible or not, remained a powerful one. That’s why the pathos is so palpable when things don’t work out as expected.
For four friends of mine at Andover—Jack Berman, Will Daniel, Harry Bull, and John F. Kennedy Jr.—things didn’t work out as expected. And that’s why I wanted to tell their stories; I just couldn’t get out of my mind that searing contrast between the infinite promise of youth and the harsh reality of adulthood.
Despite its size, Andover was really a very small and intimate place. Everyone knew of everyone else, even if we were not all close friends. So it was with me and Jack, Will, Harry, and John, all of whom I knew and was friendly with to varying degrees.
* * *
JACK WAS TWO YEARS AHEAD of me at Andover. I knew him best from the small Friday-night Shabbat services that a handful of the Jewish students on campus would attend, more for camaraderie and a sense of community than for anything particularly religious. Even then, Jack was a serious fellow who led the services with a befitting sense of solemnity and purpose. What I remember best from those weekly gatherings was the fact that we would meet in the Kemper Chapel, a grotto for the school’s Catholic students in the basement of the soaring Cochran Chapel above. Each Friday night, either Jack, Alan Cantor, or I would remove the brass crucifix from the wall and lay it on a chair on one side of the room. And then the brief services would begin, followed by sips of cheap Mogen David wine and sponge cake.
I do remember the Passover seder during my second year at Andover. It was held in Cooley House, a small modernist gathering place by the athletic facilities. There was of course plenty of sweet red wine on hand, in keeping with the Passover tradition. But kids being kids, before long a whole lot of Mogen David was being consumed. “They didn’t want to look like they were intolerant of our religion, and we just got so drunk,” Cantor said. But not Jack.
That was typical of Jack. By all accounts, he was a serious student at Andover who rarely participated in the extracurricular shenanigans that his peers seemed to find so captivating. That meant he avoided the usual adolescent black holes of drinking, drugs, and sex. “I don’t remember him ever talking about girls,” Cantor said. “He was a grown-up and consequently wasn’t a lot of fun.” He said Jack reminded him of his first-year roommate at Harvard, Mike Kaplan, who wrote in his thirtieth-year Harvard reunion notes, “I finally am in chronological balance. I’ve always been a 52-year-old man.”
* * *
I KNEW WILL A BIT BETTER THAN I knew Jack. Like me, during our first year he was in Nathan Hale House, named after the Revolutionary War martyr and built in 1966 in a style that married elements of a modern glass house with the brutalist architecture then in fashion. For the longest time during our ninth-grade year together, I had no idea that Will was Harry Truman’s grandson or that his father was the Times’ Washington bureau chief and the paper’s former managing editor. While he seemed far more sophisticated than I did, I had no idea he grew up in New York City or that he came from such rarefied stock. To me, as to others, he seemed like a younger version of Gregg Allman. His skin was “so white and pasty,” our friend Phil Balshi recalled, that Will looked “almost ghostly.” We called him “Goldilocks.”
He also seemed very smart, but also very ethereal, as if he were in a perpetual state of being high. He spoke slowly, quietly, and deliberately, and had a guttural laugh that seemed more like an ironic chuckle than anything else. Will was a smoker. The rules on smoking had evolved such that you could smoke cigarettes with your parents’ permission, but two smokers could not room together. Of course, being allowed to smoke cigarettes was the perfect cover, smell-wise, for smoking pot, and lots of people in Nathan Hale seemed to indulge in both.
I remember times, after dinner, when Will would wander up to my large single room and just sit there giggling while I chatted away about something or other. Nothing I was saying was particularly humorous. I always got the sense that Will was just hanging out in my room for his own amusement, since there must have been something about my obvious naïveté—having grown up, sheltered, in the Worcester shtetl—that he got a tickle out of when he was in one of his altered states. I certainly never participated with him in his flights of fancy, and he never asked me to. Bruce MacWilliams remembered that they both would get stoned and then Will would come visit me. “When he was talking to you, Bill, he was stoned,” Bruce said.
* * *
I KNEW HARRY MORE FROM TAKING CLASSES together—Gil Sewall’s treacherous History 35 course and his delightful History of Art course—than any other way. I always found him to be whip-smart, making one insightful counterintuitive comment after another. I knew he was one of the few people from Chicago at Andover, but I did not know he was a legacy or that his family owned one of the oldest and most successful industrial companies in the Midwest. I knew he had conservative political views that were diametrically opposed to those of nearly everyone else on campus—and certainly to mine—but he always delivered them in such a silken fashion—much the way William F. Buckley did or Bill Kristol does—that it was hard not be impressed, hard not to take what he said seriously. Although he lived in nearby Pine Knoll cluster, I didn’t socialize with him much. He was more in the Will Daniel school of extracurricular experimentation than I was. Both Harry and Will were Upper Left types; I started out in Upper Right—the land of the nerds—but as my status on campus evolved, I shifted to Lower Left, the home of the student leaders and creative types. Still, I always felt a kinship with Harry, and we always greeted each other in class, or in Commons, as good friends would, even though we were not. Maybe it was my partial midwestern roots,
maybe it was that after he arrived he was the youngest member of the Class of 1977 and I was the second youngest, I don’t know.
John, well, we all knew John.
Jack
IF THE GERMANS HAD HAD their way during World War II, there would have been no Jack Berman. Neither Jack’s father, Misha Berman, later known as Morris, nor his mother, Bluma Kamenmacher, should have survived their wartime experiences in Poland and Lithuania, let alone meet in a refugee camp in Germany, start a family, and move to America. But they did.
Jack’s older brother Norman explained how when the Germans invaded Russian-occupied Lithuania in 1941, Bluma’s family had tried to flee, but ended up stuck in the Vilnius ghetto in a small apartment with twenty-five others. Each day, Norman said, “they were marched to a factory and they worked, [then] they were marched back. They had their ration card. They ate. They didn’t eat well. The ration was about five hundred calories a day.”
Two years later, when the ghetto was liquidated in September 1943, only two thousand, or 5 percent, of the original occupants had survived. Among them, incredibly, were Bluma, her mother Feiga, and her sister Sarah (another sister, who had been smuggled out of the ghetto, wasn’t so lucky and had been shot in a roundup of Jews in another town).
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