A little more than half a century ago, New York City attempted an experiment in a handful of its public schools. In the thirteen years since Brown v. Board of Education, the city’s public schools had become more segregated. Many black parents decided that hope for their children rested in self-determination rather than in waiting for integration. Under pressure from grassroots groups, Mayor John Lindsay, a liberal Republican, approved a plan to create three locally governed school districts, in which community-elected boards would assume a degree of control over personnel and curriculum.
One of the school districts was in Brownsville, a Brooklyn neighborhood that had once been Jewish and middle class but was, by the late sixties, mainly black and poor. Starting in the fall of 1967, the new Ocean Hill-Brownsville district deëmphasized traditional grading, added curricular units on black identity and culture, and, in predominantly Puerto Rican schools, adopted bilingual teaching. The new arrangement was popular with parents, and was supported by a surprisingly heterogeneous coalition that included Black Power separatists and the liberal Ford Foundation. It was opposed by the United Federation of Teachers, which was largely white and Jewish; the union’s leader, Albert Shanker, considered the community-control effort to be a veiled attempt at union-busting. Near the end of the school year, the district’s governing board dismissed thirteen teachers and six administrators—nearly all of whom were white, and critical of the new arrangement. Rhody McCoy, the district’s administrator, said that “the community lost confidence in them.” The union insisted that the dismissals were illegal. Local teachers went on strike. In September, 1968, the strike went citywide.
Gary Simons, the son of a housepainter and a homemaker, had just been hired as a teacher at P.S. 140, an elementary school in the Bronx, his home borough. When the strike reached the Bronx, he was living with a roommate about a half hour north of the school, in the upper-middle-class neighborhood of Riverdale. As the days passed, he noticed that teachers in Riverdale and other rich areas were convening in synagogues, churches, and community centers, continuing to educate their students, albeit unofficially. In the South Bronx, the schools were simply closed.
“That bothered me,” Simons said recently. I’d gone to see him in New Milford, Connecticut, where he has lived for a decade, a late-in-life refugee from the city. Simons has a wide face and a John Bolton-like mustache; he had recently had surgery to remove cataracts from both of his cloudy-day-colored eyes. His house is full of glass-enclosed wooden bookcases, in which he keeps a growing collection of hardback first editions of the books he considers to be the most important in the world. The walls are packed with pictures, many of alumni of Prep for Prep, the educational nonprofit that he founded ten years after the strikes. Prep, as its alumni call it, conducts an annual citywide talent search for high-achieving students of color, then administers a battery of exams and interviews. The kids who are accepted by the program agree to spend the summers before and after sixth grade in classes five days a week, and to attend classes on Wednesday evenings and all day on Saturdays during the intervening school year. In exchange, the program secures spots for them at New York’s most selective private schools. (The organization’s Prep 9 program sends high-school freshmen to boarding schools in the Northeast, such as Deerfield Academy and Choate Rosemary Hall.)
Simons speaks in a nasal and faintly sibilant Bronx lilt, allowing his vowels to accommodate extra syllables mid-thought; sometimes he ascends to a high, gravelly whine when remembering surprise, or confusion, or anger. Back in 1968, he told me, a few teachers at P.S. 140 decided to break the strike early. “I probably was the only white teacher from the school that went in,” Simons said. Among the union’s black members, the strike was widely seen as a racist backlash against a brief moment of black empowerment. When the strike ended, in November, Simons said, he was “sort of persona non grata.” He and another teacher were assigned to a first-grade class with thirty students. Three of the kids, he quickly noticed, were far ahead of the others academically—almost disruptively so. The teachers eventually put them in a separate reading group. “And then, when we got to a certain point with the three of them,” Simons said, his face brightening with the memory, “it was very clear that one was much abler than the other two.”
When Simons was young, his father would sometimes come home with armfuls of flowers from the garden of a house he’d spent the day painting on Long Island. On the acre behind his home in Connecticut, Simons tends to a bevy of flowers and bushes and impressively large trees. Now, as he spoke about that talented first grader, he looked a little like a horticulturalist recalling a prize pack of seed. By the spring of 1969, Simons was going regularly to the boy’s house to tutor him. The kid sped through the lessons for advanced second graders, and was ready for third-grade reading, but, in the summer, Simons had to return to his own studies, at Columbia Teachers College. When school started again, in the fall, the three advanced students were given reading that was several levels below where they’d left off, on the assumption that low-income kids inevitably slid backward over the summer. Simons was furious—he resolved to make extra efforts on behalf of his especially gifted students. One year, when he was teaching third grade, a “group of about six parents marched themselves into the principal’s office and insisted that I be able to take the kids on to fourth grade,” he said. A few years later, he shepherded a fifth-grade class to the end of elementary school, and then contacted several prep schools on the students’ behalf, assuring the admissions and financial-aid officers that the children would fit right in at their exclusive institutions. Among these students was a son of Puerto Rican immigrants named Frankie Cruz, who would go to Calhoun and Hotchkiss and later become a poster boy for Prep. Simons’s lucky discovery of him is something like the program’s founding myth.
Simons knew that there were bright but understimulated kids all over the city. Maybe, he thought, he could place more of them at schools worthy of their talents—new lilies in the old soil of élite education. In 1978, he secured funds from Columbia and from a Sears in the Bronx, hired a few teachers, and got space for classes at the Trinity School, on the Upper West Side. Trinity’s headmaster, Robin Lester, became an evangelist for Simons’s mission. “I used to call him St. Gary,” Lester told me. Most of Lester’s peers didn’t see a fresh influx of minority talent as a top priority, but a few younger admissions officials and school heads, shaped politically by the civil-rights movement, were immediately on board. The plan that Simons had outlined for Prep for Prep echoed the approach of A Better Chance, a national organization that was founded in 1963 to help poor black students and now focusses on ethnic diversity without attention to income. (Notable alums include the recent Presidential candidate Deval Patrick and the singer-songwriter Tracy Chapman.) These administrators were part of a vanguard that would eventually establish diversity of this sort—the simple fact of more nonwhite faces in a room—as a preoccupation of their profession.
Simons knew nothing about management, or what it would take to raise money from wealthy people for an annual budget. “To me, a board was a piece of wood,” he said. But he had strong opinions about what the kids should learn. He also “had a work ethic to beat the band,” according to Dominic Michel, who worked as a deputy to Simons for many years. Simons held staff meetings that stretched into the evening, and he assigned his students piles of homework. When he described the course of study to the admissions director at the Ethical Culture Fieldston School, she said, “Gary, if by the end of the first summer there are four or five kids still standing, pin a badge on each one of them and quit while you’re ahead.”
I was accepted by Prep in the spring of 1996, at the age of eleven, and my life has, in many ways, ordered itself around this early and somewhat arbitrary triumph: when I was a kid, I did well on a test.
I was a soft and oversensitive only child, afraid of failure. During my first week of classes, I would sit at home, in my makeshift study at the dining-room table, holding my head in my hands, overawed by the amount of work I was being asked to do. The kids I met at Prep were bright and hyperverbal; even the ostensibly cool among them had an obvious nerdiness that they had stopped hiding now that they were away from their normal schools. Rounds of Magic: The Gathering, a role-playing card game, turned gladiatorial at lunch; Tamagotchis—small electronic Japanese toys on which you’d tend to a digital creature—were passed around like samizdat pamphlets. We were a hundred or so of a kind, all humming with the seductive feeling of having been called out from a crowd. Grouped into small units of about ten, and placed under the charge of high-school-age and college-age advisers who’d gone through the program before us, we quickly developed fellow-feeling. What we had most in common were noodgy, hard-driving parents, the type of people who’d push their children to attend supplemental schooling for a year and a half.
Some of my new friends had horror stories about their schools. They talked about walking through metal detectors and sitting through fights in classrooms where there were more than thirty or forty students. That wasn’t my experience. I’d been attending a Catholic boys’ school in Harlem, where all the students were black or Latino, except for one white kid named Alex, who always looked bewildered. We wore slacks and ties and memorized the names of the books of the Bible. I had to write weekly essays for a class called Literature, Speech, and Writing and recite them aloud. The sweet, stern woman who taught the class judged our performances, on composition and delivery, and gave chocolate to those who did best. When I was in trouble—I was often in trouble—I’d have to stay after school and write some bland penitential sentence a hundred times, until my wrist was sore and the meat of my hand was numb. This was called JUG, for Justice Under God.
At Prep, the only G whose justice we feared was Gary. On many Friday afternoons, at lunch, in the Trinity cafeteria, Simons would stand before us, his mustache hiding his mouth, and rattle off a fresh list of kids who had left or been dropped from the program, because they couldn’t keep up. Even more powerful than the fear of dismissal was a kind of wonder at our exotically well-resourced surroundings. Trinity’s science labs had smooth tables and deep sinks, Bunsen burners and goggles, powerful microscopes we used to scrutinize slides of our own cells. There was an Olympic-size pool in the basement and turf on the fenced-in roof, both open to us at recess. We were being prepared academically, but we were also being made to understand anew what a school could be.
Our instructors gave us a foretaste of the eccentric and informal adults we would meet at the prep schools where we would later be placed. I studied Latin with a wisecracking Englishman who made constant, morbid fun of Caecilius, the Pompeian nobleman who was our textbook’s protagonist. (“Caecilius est in horto,” we’d recite. “And now,” the teacher would say, pantomiming horror at an exploding volcano, “Caecilius mortuus est.”) The literature curriculum moved swiftly through lighter fare, such as Conrad Richter’s “The Light in the Forest” and Maia Wojciechowska’s “Shadow of a Bull,” to potentially age-inappropriate stuff, like Richard Wright’s “Black Boy.” I read the latter under the close attention of kids in their second Prep summer, who told us younger ones the pages where we could find the hanging of a kitten and loose bits of racial-sexual reverie.
If you were having trouble in class, you were supposed to ask for a meeting with a teacher. For no reason I can determine, apart from my mother over my shoulder in the dining room—sometimes she’d sit at the computer and transcribe my essays as I spoke them aloud, like a prepubescent Milton—I learned to love the program, and made it through.
Two decades later, on a July afternoon, I visited Trinity again, where a new batch of Prep kids was missing out on a lovely day. Bluish light streamed into the classrooms as if to tease the suckers within. The typical Prep contingent has about a hundred and twenty-five students. They are bused from all over the city to wherever Prep’s courses are being held—usually Trinity—and divided into classes according to math aptitude. Every first-year kid takes a period of literature, a period of intensive writing instruction, a period of history, a period of laboratory science, and one or two periods of math. Most also take Latin. I peeked in on a second-summer literature class, where students were talking about Odysseus and his lonely though by no means solitary ramble around the ancient world’s mythical-physical map. The teacher wanted to know what the students thought about his character—what it meant when he asked for and accepted help, and whether his virtues in any way mitigated his obvious, trip-extending flaws. Kids piped up one by one, each adding to the class’s group portrait of the wave-tossed, homesick man. I recognized the approach: Prep’s teachers often use literature to teach something akin to ethics, and to illustrate the values that might be useful in succeeding at, say, a challenging new school. Elsewhere, in a long-standing Prep class called Problems and Issues in Modern American Society, students discussed the carceral state and its effects on black communities.
I saw love and care reflected by each detail in the room: the bright backpacks, the pressed clothes, the manners and the syntax that had been hammered into place by parents anxious about how their children might be seen in the world. (My mother hunted slang and unconjugated verbs as if they were big game.) Like the parents in Brownsville, they had noticed something amiss in the system that was supposed to steward their kids, and they had made a bid for control. I knew how radically these efforts might change one’s life: my wife and most of my best friends are Prep alums; much of what I have that is good I can trace back to the program. The change isn’t only personal. No matter the context, certain privileges accompany being thought smart: teachers kindle your ego; people listen when you talk. And, at a mostly white private school, in a society eager for signs of success, each plucked-out black or brown kid carries an unspoken message. With every new way of seeing comes, subtly, a new way to be seen.
There were criticisms of Prep’s methods from the beginning. People asked Simons whether it was wrong, in a system marred by disparity, to focus on students already advantaged by their intelligence. This concern made him livid, he told me. “It is precisely these kids who are losing the most, because of the difference between what they’re achieving and what their potential is,” he said. Simons regarded human intelligence as a special substance that, if left untapped, would sour, and he believed that this was happening all over the country. “He thought, in some cases, that we were producing very gifted criminals,” Lester, the Trinity headmaster, told me. Simons studied at Teachers College under Abe Tannenbaum, a pioneer in the identification and teaching of “gifted and talented” children. Each Prep applicant takes an I.Q. test—I remember solving puzzles in a wood-panelled room on the Upper West Side, stressed about my speed. When I spoke with Simons in Connecticut, he frequently, and with obvious relish, launched into tangents about various kinds of I.Q. tests, and about how a stellar writing sample could, in rare cases, trump test scores.
By the time I went through the program, in the mid-nineties, Simons had more or less acclimated to life as a nonprofit executive—and Prep, bolstered by a highly motivated board of directors, was easily raising the money to cover its yearly budget, which had grown to several million dollars. New York had put the program on its cover in 1985, along with the headline “The Best Prep School in Town.” In 1986, Simons created the Lilac Ball, an annual ceremony for Prep students who have been accepted to college. The event doubled as a large fund-raising gala, and quickly became a fixture on New York’s philanthropic circuit.
Simons had also developed what he believed to be his best idea yet: a so-called summer advisory system, which employed older Prep students as mentors to guide younger kids through the first summer, making life easier for newbies and insuring a loyal and motivated body of alumni. To lead the effort, Simons tapped Frankie Cruz, who was about to graduate from Hotchkiss. Cruz headed up the summer advisory system during his college years—he attended Princeton—and then went to work for Prep full time.
By showing how much demand there was among private-school admissions officers for exceptional students of color, Simons established a template. Oliver Scholars was created in 1984, to prepare “high-achieving Black and Latino students from underserved New York City communities for success at top independent schools and prestigious colleges.” The Posse Foundation, which recruits talented high schoolers and sends them in small groups to a number of selective colleges and universities, was founded in 1989. An economy was growing, and its chief product, smart black and brown kids, was increasingly visible, if still decidedly outnumbered, on élite campuses. But Simons was restless. He’d envisaged Prep as a simple series of chutes out of poverty and the working class. Now he saw how to make it something more. Each year, Prep kids were being voted class president or head of student government at their schools. “I began to realize that although, initially, my intention was to give these kids a chance because I thought it was just outrageous how the deck was stacked against them,” he told me, “these kids were also potentially, like, national treasures. And not to have their potential developed is a loss to everyone else.” He decided that Prep would become a “leadership development” organization. “I realized that this was a way to raise a lot more money, on the basis that the larger society stood to gain,” he said.
In the mid-nineties, Simons called Charles Guerrero, a Prep alum who grew up in the Bronx, went to Harvard, and then moved to San Francisco, in part to start a theatre company with a group of his friends from back East. “Prep had a reputation at the time—sometimes deservedly so—that they only pushed people toward business and law, and if you did something a bit weirder you’d be off their radar,” Guerrero told me. Simons, known for having favorites, supported Guerrero’s adventure in art. Later, Guerrero became one of Prep’s longest-serving employees. He’s now the director of admissions at his alma mater, the Ethical Culture Fieldston School.
Simons asked Guerrero to look over his plan for a new leadership curriculum. “I thought it’d be five or six pages, so I said sure,” Guerrero told me. Soon, a stack of more than a hundred typewritten pages arrived in the mail. Simons laid out a three-part course of study—which included reading assignments, classroom sessions, movie screenings, and hours-long role-playing simulations—that would identify the “attributes,” “ethics,” and “tactics” of leaders, focussing on the difficulties inherent in a pluralistic democracy. This curriculum, called Aspects of Leadership, began with a few specially selected students but soon became mandatory for high-school-age Prep kids. For many years, the classes were held at an estate in the village of Wappingers Falls, New York, where kids would stay for three nights at a time, during winter and spring breaks. (Now, to save money, they’re held in the city, and have no overnight component.)
The curriculum was an extension of what Simons called the “Prep ethos,” which he’d been trying to impart informally all along. In the early days, when the program was still serving a fairly small number of kids, he’d sit them down in a hallway after a long Saturday of grinding work and give motivational speeches, to remind them of the rewards that awaited if they just kept going. One of the signature classes at Prep, on ethics and personal responsibility, is called Invictus, named for the William Ernest Henley poem: “I am the master of my fate, / I am the captain of my soul.”
“One thing that I didn’t always articulate—but, if you think about it, it’s built into the whole fabric—is that I have always been appalled at the whole ethos of victimization,” Simons told me. “Because, if you get people to subscribe to it, it’s like squeezing all the air out of the balloon. You’re taking away the psychic energy that could propel them.” When he talked to prospective parents, he made this point again and again. “One of the things we’re going to be doing is telling your kids every which way from Sunday that they can do it,” he recalled saying to parents. “That whatever obstacles remain”—racial, social, economic—“they can overcome them. If the message you’re giving your kid is directly contrary to that, it’s too much cognitive dissonance for an eleven-year-old to be asked to deal with.”
For some, this emphasis on the individual ability of a handful of students is a fundamental flaw in the program’s design. Nikole Hannah-Jones, the Times journalist who created the 1619 Project—which marked the four-hundredth anniversary of black people’s arrival in the Americas with a multifaceted argument about the persistent effects of slavery and its aftermath—is writing a book about school segregation. She told me that programs like Prep obscure the system’s deep inequalities. “They allow us to say, ‘If kids really wanted an education, if they wanted to work hard, they could get it. Look at this program! They can apply for this program!’ ” she said. “And it allows us to sustain all the other inequality and feel O.K. about it, because we’ve given this very small avenue to this small number of kids who ‘wanted it.’ ”
One summer day, I visited an N.Y.U. building on the eastern edge of Washington Square Park, where an Aspects of Leadership session was taking place. In recent years, Prep has added an extra day to the retreats, called Day 4, during which students design and lead their own lessons. A group of maybe a dozen high schoolers were standing side by side in a wide hallway, participating in an exercise meant to illustrate the workings of privilege. “Take a step forward if your parents own their home,” the girl who was leading the exercise shouted out. “Take a step back if your parents don’t speak English as a first language.” When the exercise was over, the person farthest ahead was Mike O’Leary, a peppy visual artist who helps run Prep’s leadership programming and who was the only white person in the room. I couldn’t help but imagine Simons rolling his eyes.
Prep was built atop a fault line of American education. In 1778, shortly before he became the governor of Virginia, Thomas Jefferson drafted A Bill for the More General Diffusion of Knowledge. In Jefferson’s vision, all the free boys and girls in the state would spend three tuition-free years learning “reading, writing, and common arithmetick” and becoming “acquainted with Græcian, Roman, English, and American history.” Of the boys in each district whose parents were “too poor to give them further education, some one of the best and most promising genius and disposition” would go on to grammar school. The others—along with all the girls and the nonwhite children—would be left behind. Jefferson’s bill gave rise to the Act to Establish Public Schools, which the state passed but largely ignored. It was not until the “common school” movement gathered momentum, in the eighteen-thirties and forties, that public education began, gradually, to take hold. The movement’s ideals were most famously promulgated by the Massachusetts reformer Horace Mann, who believed that education could be “the great equalizer of the conditions of men.”
When Teachers College was established, in 1887, it created an experimental school, and named it for Horace Mann. It is now a notoriously exclusive preparatory school that sits on a grassy campus overlooking Van Cortlandt Park, in Riverdale. This is where I was placed, by Prep for Prep, in the fall of 1997. Thanks in large part to R. Inslee (Inky) Clark, the school’s Waspy, charismatic headmaster from 1970 to 1991, it had become a much more racially diverse school than it had been just a generation before. In the late sixties, Clark had been the director of admissions at Yale, and had helped establish relatively meritocratic admissions standards there, welcoming a stream of Jewish students and then, increasingly, students of color. He also helped initiate coeducation. Clark signed an agreement with Simons, reserving spots in each seventh-grade class for Prep students. (Several years ago, the Times and this magazine reported that Clark, who died in 1999, had presided over a widespread culture of sexual abuse of students. The athletic field at Horace Mann that bore his name when I was there has been renamed Alumni Field.)
Nine other Prep students arrived at Horace Mann with me. There were other black and brown kids already on campus, most of them also from Prep or similar programs. In the cafeteria, a group of tables we collectively called the Middle Table was informally reserved for the darker skinned; we often pushed the tables together and used them to anchor marathon games of spades and rounds of the dozens. We were theatre kids and singers, athletes and library shut-ins, student politicians and social outcasts and “loungies” (vaguely political punks who hung out in the student lounge). I straddled worlds, trying and failing at sports, eventually settling for being the manager of the football team; I sang in the glee club and in the boys’ ensemble, flitting around the city in a blazer and khakis, harmonizing under Christmas trees in office lobbies. I performed in musicals, too. One year, I played the villain in “Carousel,” a seafaring baritone named Jigger. A very kind white English teacher pulled me aside to make sure that I wasn’t worried about the unfortunate rhyme.
At meetings of the Union, Horace Mann’s multicultural club, we watched standup specials and satirical movies like Spike Lee’s “Bamboozled” and puzzled over how our favorite artists had turned the country’s lousy realities into something joyful. Alongside my friends, from a jarring double vantage of privilege and its lack, I came to know America better, and began honing my responses to it. I also left America for the first time: during my junior year, my Japanese teacher led a trip to Tokyo, where I spent a few days with a host family, at whose table I ate profusely, terrified to offend, and spoke stilted Japanese in nervous bursts. The next summer, I went with the glee club on a tour of the Baltics, where we sang Verdi’s Requiem in huge churches in Tallinn, Helsinki, and St. Petersburg. I knew, without ever being explicitly told, that this kind of rare experience was just as much the point of prep school as what I learned in any of my classes.
One night, during an after-school concert in the Horace Mann cafeteria, a rumor crept through the crowd. It was the winter of 2000, and we’d all been following the story of Amadou Diallo, a young Guinean immigrant who had been shot and killed—forty-one shots, nineteen bullet wounds—by four New York City police officers; they had supposedly mistaken him for a rapist on the loose. An older boy named Damien, also a Prep kid, a football player with a high, flutelike voice—who, later that year, would be elected student-body president—pulled me outside, into the cold, and broke the news: the cops had been acquitted. We cursed and shouted for a while, then just stood there, backs against the wooden fence that ringed the athletic field, shaking our heads.
My friends were my world, and I realize now that I never thought to hope for more than that. Recently, I had dinner with one of them, a classmate at Prep and at Horace Mann named Chris, who is now a private-school teacher and administrator. The Times had just published the first installment of the 1619 Project, and, on a WhatsApp group chat that my high-school friends and I have maintained for years, Chris said that a project like that would have changed our lives if it had come out when we were younger. At dinner, over Chinese food, I asked him what he’d meant. Had we needed our lives to be changed? Was high school tougher for us than it was for others? If I was angry then, or had a chip on my shoulder—a thing I was told more than once; I must have learned the phrase around that time—who could really say why? But, even as I asked these questions, one after another in a quick, strained bunch, I wondered why I suddenly wasn’t sure I wanted to hear his answers. Chris raised his brow, looking compassionate but also ready to laugh, and asked me about Halloween during our senior year. I had dressed up by wearing my usual dark-gray hoodie but with a sign strung from my neck that said “The Black Kid Who Stole Your Bike.” “You were obviously working through something,” he said.
When I talked with Simons about the arguments against Prep when it began, he said people had told him that Prep kids were “going to have lots of problems socially. They’re not going to know who they are. You’re going to mess with their minds and their sense of identity and blah, blah, blah, blah. I was getting that from a whole lot of liberals. They were a bigger problem, initially, than conservatives.”
In January, 2019, a video showing two students wearing blackface and acting like monkeys surfaced at the Poly Prep Country Day School, in Brooklyn. A demonstration ensued; one of the protesters was the daughter of Diahann Billings-Burford, a Prep alum who started at Poly Prep in the mid-eighties, and later served as New York’s first chief service officer, overseeing volunteer programs, during Michael Bloomberg’s administration. (Bloomberg has been a major donor to Prep and is a onetime trustee.) Billings-Burford is now the C.E.O. of the Ross Initiative in Sports for Equality. “The kids reached a point where they said, ‘This is not O.K.,’ ” she told me. “They were, like, ‘This is our school, and if you valued us you wouldn’t ask us to feel like this.’ ” On Martin Luther King, Jr., Day that year, a multiracial group of students wore all black and boycotted classes.
The incident reminded Billings-Burford of her time at Poly Prep. Late in 1986, a young black man named Michael Griffith died after he was beaten by a mob of white men in Howard Beach, Queens. “Some of our white friends were, like, ‘You don’t understand, it was just where he was, it wasn’t a race thing,’ ” she recalled. “There wasn’t a space to discuss these issues.” She later became the head of the student government, and, against the wishes of the school’s administration, she led a group of students in creating Umoja, Poly Prep’s first black-student group.
Jackson Collins, another Prep alum, now serves as the program’s associate executive director. He’s also the author of a doctoral dissertation about the experiences of students of color in private schools. He surveyed more than five hundred Prep students and measured their happiness according to three variables: “sense of belonging,” “emotional wellbeing,” and “racial coping self-efficacy and competence”—i.e., how someone reacts in a moment of racial tension. Among older generations, Collins has found, avoidance is a common tactic, but, he told me, “students and their families are much more candid now, much more outspoken.”
A few months before the Poly Prep incident, Prep for Prep, which was celebrating its fortieth anniversary, held a symposium at the Schomburg Center for Research in Black Culture, in Harlem. Alumni and staff walked through the building’s atrium in neat suits, vibrant dresses, and polished shoes; bronze light fell from high windows. People hugged and shouted at one another and flagged down favorite teachers they hadn’t seen in a while. The symposium featured panels on education and on electoral politics, and during the Q. & A. portions people got into good-natured arguments and tossed out earnest ideas. Should we form a Prep PAC to support political candidates who share our values? Should we start a school of our own?
Prep’s current chief executive is Aileen Hefferren, who was the program’s operations director and, later, its fund-raising chief before succeeding Simons, in 2002. She has the efficient mien of a newly elected congressperson—speaking quickly and affably, calling dates and figures frictionlessly to mind, swerving purposefully between budgetary and programming specifics and the program’s guiding ideals. For the final session at Schomburg, she spoke with Leslie-Bernard Joseph, then the chair of Prep’s alumni council. (He is now the C.E.O. of the Coney Island Prep charter-school network.) During the Q. & A. that followed, a tall young alum wearing a floral shirt and a skeptical look stood up. “I want to know,” he began, “whether you feel that there needs to be an ideological shift from a white-supremacist, élitist mentality that Prep is at minimum participating in, if not encouraging or propagating.” The crowd quieted, and he went on. Many of the Prep kids he knew and had mentored had a “fraught relationship” with “this Prep identity,” he said, “given Prep’s relationship with white-supremacy norms.”
Joseph, who is black—and who looked, to me, as if he sensed the peril inherent in the question—spoke before Hefferren, who is white, could. “There is an answer you want, an answer Aileen believes, and an answer Aileen can give,” he said, suggesting that, rather than making her offer any of those, he would field the question. Then he steered his answer toward a pitch to his fellow-alumni: those who are active in fund-raising and charitable giving can bring about the changes they want to see, he said.
I later tracked down the young questioner. His name is Anthony White. He went through Prep 9, attended Choate Rosemary Hall and Georgetown, and got jobs in finance—first at Barclays, then at Credit Suisse, which has a long-standing relationship with Prep. (A number of Credit Suisse employees have served on Prep’s board and have been major donors to the program; the bank frequently hires alums as interns, and many go on to work there.) White told me that he had no love for banking but that the money was more than anybody in his family had ever earned, and that he used it partly to provide financial security for his mother and younger sister. He’d worked as a Prep adviser in the summers and, since finishing college, had continued to mentor Prep students. Many of them, he said, felt torn between their genuine interests and what they felt Prep expected of them.
“A lot of people I know are unhappy with what they think Prep wants their lives to be,” he said. “The mission itself is élitist. And when you have a mission that’s élitist, and then you use these institutions that are élitist, it’s difficult for children or teen-agers to even have a healthy self-esteem. A lot of them want to figure out how they can decide their identities outside of these rarefied spaces.”
White had always wanted to be a musician. As he talked to these students, he realized that he couldn’t advise them in good conscience if he wasn’t living his values. He quit his job at Credit Suisse and used some of his savings to start recording music as well as a one-man podcast about pop culture and current events called “The Black Sublime Podcast.” He now works as a server at a restaurant in Greenwich Village.
“My real question to Aileen,” he explained, “was: How are you going to protect the psychologies of these kids?”
A few years ago, the sociologist Anthony Abraham Jack conducted a study of the experiences of undergraduates of color from low-income backgrounds who attend élite private colleges. Drawing from nationwide data and his own research, he found that half of these students are graduates of private day schools, boarding schools, or college-preparatory high schools. The study became the basis for his book “The Privileged Poor: How Elite Colleges Are Failing Disadvantaged Students.” Class mobility via élite education is not usually an up-from-nothing story. What is more common, in the relatively rare instances of mobility which our society currently provides, is a series of institutional incursions, which lend a kind of jerry-rigged privilege to a chosen few.
Ed Boland worked in Yale’s admissions office before becoming Prep’s head of external affairs. (He left Prep in 2018.) He first heard about Prep, he told me, during the admissions season of 1989. Everybody had a vague sense of what a prospective Yale student looked like, he said. “They’ve got grades like this, and scores like this, and attended a summer camp in Maine with a Native American name, and worked at a soup kitchen in France, and had internships at their father’s bank,” he said. “These experiences are how we have shaped our leadership class for a very long time.” He went on, “But, on this particular afternoon in ’89, there was this whole crop of kids who had the same kind of Park Avenue pedigree, but with outer-borough addresses. This was not, I hate to say it, your typical ‘scholarship kid.’ These kids were every bit as strong, and every bit as credentialled—and I’m not just talking grades and scores. The whole package was very Park Avenue.” Prep had helped its students not only do well at demanding schools but also signify a kind of social standing. “Prep for Prep is like a stimulus package for an individual,” Jack told me. My friends often joke that, instead of a rich parent or a working social safety net, we had Prep.
In 2002, I left New York City for Vermont, to attend Middlebury. There, I learned what a Wasp was. I met kids who had gone to East Coast boarding schools and their analogues in the Midwest and San Francisco. They wore Patagonia fleeces and drank entire glasses of milk at meals. They carried Nalgenes full of water which never seemed to empty. They were friendlier than I knew what to do with.
I also met black kids from other states—North Carolina, Washington, Massachusetts—who belonged to the suburban middle class. We couldn’t read one another: they came from families richer than mine, but my education had been tonier. Many of the black Middlebury students who came from New York had attended segregated public high schools in Harlem and the outer boroughs. A few had applied to Middlebury directly, but most had come through programs like the Posse Foundation. (Equality, I was learning, depends so much on mediation, at every step along the way.) These other New Yorkers mostly seemed smarter than I was, but they had not spent the previous several years being initiated into upper-crust education and its folkways. In my early days on campus, I was told more than once, by basically nice white classmates, how much different my speaking voice was from those of the other kids from New York they’d met. What this meant, I knew, was that I sounded, to their ears, sort of white, and that the others didn’t.
The academic work wasn’t any harder than it had been at Horace Mann, but, by my sophomore year, something in my approach to it had unscrewed itself, fallen loose. I was still diligent about art—singing and doing my best in plays and beginning, tentatively, to write—but, that spring, I stopped going to class, and let late essays pile up. After a flunked semester, I was sent home to New York for a probationary term: I would take classes at Hunter College, part of the City University system; if I earned a B average, I could return to Middlebury. I went home, got the B’s, and headed back north. Then I found out mid-semester that I was going to be a father, and I promptly flunked out again.
Twenty years old, frazzled, living with my mother, and in terrifying need of a job, I landed a low-level position at a hospital. On the day I was supposed to start, I couldn’t will myself to go. Maybe I was feeling squeamish about the blood and shit that my interviewer, a kind-looking black woman, had taken pains to inform me, in a don’t-act-surprised-when-you-show-up tone of voice, would be a constant part of the job. Or perhaps it was the way that she’d said, with something like suspicion, but also with something like concern, “Do you think you’re maybe overqualified? I’m surprised you want this job.” As if, really, she meant to say, “It looks like you’re on a much different path from this one. Keep going.”
My daughter was born in the fall of 2005, when I should’ve been a college senior. I got another job interview, at a well-known education nonprofit in Harlem. The interviewer was tall and heavyset and wore a T-shirt bearing the nonprofit’s name in bright letters. As he looked at my résumé, he dragged his eyebrow upward, squinching his forehead into folds. In the summers between school years at Middlebury, I’d worked as a teaching assistant at Prep. “I’m sure that was really nice,” he said. “Lotta smart kids.” I knew where this was headed. “But, you know, real classrooms—classrooms like ours—aren’t really like that. Have you ever broken up a fight? Had a kid curse at you?”
It is an odd feeling to watch yourself be seen—or, worse, read. I was being interpreted, reasonably but not totally accurately, according to the schools I’d gone to and the kinds of jobs I’d had. I didn’t feel like a member of the class to which my education said I was someday supposed to belong. I felt like what I was: young, black, jobless, an unmarried father. I wanted to tell those interviewers that I was afraid.
Then Prep stepped back into my life. Luck. A stimulus package. I got a job at the program’s headquarters, a brownstone on West Seventy-first Street, shuffling papers in the basement. The job required focus, bureaucratic speed, and an ability to communicate regularly and clearly with a Prep administrator whom I’d known since I was a kid. I was not good at this job. Piles of paper turned my desk into a model skyline. Information went unfiled, spreadsheets unfilled. Whatever I’d learned at school, it hadn’t been this.
So Prep recommended me as a tutor for the teen-age son of a black investment banker who was on Prep’s board of directors. The banker paid me directly, by the hour, and I sent him occasional e-mail updates on his son’s progress. We read plays and short stories and articles from the sports pages, and ran through long sets of simple algebra. The kid didn’t like to concentrate; I could relate. One day, I got a call from his stepmother, who was from Chicago. She was supporting a young Illinois senator who was preparing to run for President. His campaign was setting up a fund-raising office in New York, and they’d need an assistant. I knew that I was stumbling into another unmerited adventure. Without having finished college, I rode the first Obama campaign all the way to Washington, D.C., where I worked at the Democratic National Committee, raising money, and then at the White House, where I helped recruit minor functionaries to work at Cabinet agencies. On Friday evenings, I’d throw clothes into a duffel and catch a BoltBus home to hang out with my daughter—and to spend most of each Saturday on the Upper East Side, pecking away at a degree from Hunter College.
I had run up student-loan debt at Middlebury, and I was paying my way through Hunter credit by credit, up front and in cash. Some semesters, out of fatigue or because I was flat broke, I gave up school entirely. Once or twice, I convinced myself that I should quit, that I’d made a fine beginning for myself—unreasonably fine, given the circumstances—as a college dropout. But something about the difficulty of this arrangement, and its maddening slowness, helped me focus. At Hunter, what I learned, I learned well, and in a hungry way I hadn’t really experienced since high school. It was the first time since fifth grade that I’d attended a public school. I wasn’t advancing anyone’s notion of diversity. My classmates were New Yorkers, and therefore from everywhere. Everybody had at least one job, and lots of them had two or three. Nobody strolled across a quad to class—Hunter has no grass—and everybody was always on the train. Many of my teachers were adjuncts, shuttling between one city campus and another; they managed, mostly, to project total sincerity about the subjects at hand. Nobody complained when, lacking a babysitter, I sometimes brought my kid to class. Nothing depended on my presence. I didn’t signify.
One professor, a white woman with graying hair who wore a series of rumpled shirts, wept while recounting the events of the twenty-fourth book of the Iliad. By the time she finished, my eyes were puddling, too. I studied the Hebrew Bible with an instructor in his seventies who tape-recorded each of his digressive lectures, intent on one day turning them into a book. A garrulous Southerner taught me early American literature: Winthrop, Edwards, Mather. A fastidious graduate student with a sideline in editing technical manuals taught a seminar on Japanese cinema and another class focussed solely on Kurosawa; I took both, and now, rereading my essays for those classes, I can see that I was starting to learn how to make my close readings bearable as prose. When I finally graduated, at a huge, happily impersonal ceremony at Radio City Music Hall—Chuck Schumer was the featured speaker—I was living in New York again, writing speeches for minor executives at an N.G.O., a few months away from turning thirty. “Twelve Years an Undergraduate,” I joked with my friends.
Gary Simons stepped down as Prep’s director shortly before I first left for Middlebury, in 2002. His ouster registered as an earthquake among the alumni, who regarded him both as a father figure and as a remote, eccentric guru. Simons had long presented himself as a kind of educator-saint, and his air of extra-professional intensity had started to wear thin with the board. He had insisted on involvement in every aspect of Prep’s operations—including maintaining personal relationships with students, which the board found inappropriate but Simons felt was intrinsic to his work. Although Simons was in tune with the individualism of the age, his shambly persona, tendency to micromanage, and allergy to compromise put him out of step with the era’s technocratic drift.
“By the end,” Peter Bordonaro, the longtime director of Prep 9, told me, “he was sort of impossible to deal with.” A stocky seventy-five-year-old with a dark mustache, Bordonaro, who left the program six years ago, has a philosophical air but speaks with the blunt diction of a lifelong teacher. He is a beloved figure among Prep alumni. We met on a cool day not long after Christmas, at a diner in the West Village. He told me that he’s tried not to obsess over Prep since he left, and that he was working on a memoir of his time in Vietnam. He recalled a day, in 1999, when Simons charged into his office and presented him with a memo titled “Prep for Prep in 2000.” In it were ten brief—brief for Simons—ideas on how Prep should adjust to a new millennium. One was a plan to focus on young Latino immigrants. “He wanted to find the kids, give them a year of English-language training, and then have them start the preparatory component,” Bordonaro said. These days, I noted, a program like that would register as a fairly unsubtle rebuke of the Trump Administration. Would that play well at private schools? “And the fund-raising—Prep’s always had to avoid seeming partisan,” Bordonaro said.
After leaving Prep, Simons almost immediately started a new nonprofit, Leadership Enterprise for a Diverse America, which, among other things, searches the country for exceptional high-school students in under-resourced communities and helps them gain admission to prestigious colleges. The program is not restricted to students of color; typically, about a tenth of the kids are white. (Simons stepped down from leda after just a couple of years, because of medical problems.)
Hefferren was, in some ways, an obvious choice to replace Simons at Prep. She knew the program well and had an extensive background in fund-raising. The educational landscape in New York was shifting: the year that Hefferren took over Prep, Bloomberg was elected mayor, and assumed unprecedented control of the school system. He closed schools, opened smaller ones, and implemented a program of “school choice,” in which city residents could apply to attend middle and high schools across the city. He also encouraged the growth of charter schools. Nominally public entities, charters are often run and partially financed by private boards of directors; they can hire non-union teachers and can recruit from a broader pool of students than traditional public schools can. They can also, crucially, craft their own curricula. Some of the donor money that once flowed to Prep began drifting toward those institutions. Philanthropists tend to swim in tight schools, often under the influence of a small group of paid charitable advisers. Ed Boland told me, “Now we often hear, ‘I’m very attracted to how successful your program has been, but I’d rather support public schools.’ ” Prep’s budget is now thirteen million dollars; its partner schools offer more than thirty-five million dollars in financial aid to Prep students annually.
This past fall, Leslie-Bernard Joseph—whom I’d seen talk, a year before, with Hefferren at the Schomburg Center—received Prep’s annual Alumni Prize. He accepted the award at a private ceremony for generous donors, and took the opportunity to make an announcement. “Prep cannot say with integrity that it fulfills its mission until it has diverse executive leadership that reflects the communities it serves and represents,” he said. “What got us here will not get us through.” He said that he wanted the five thousand dollars that came with the prize to be used to help fund the search for a new chief executive.
Hefferren, approaching her twenty-fifth anniversary with Prep, had, in fact, already submitted her resignation to the board. Less than a month after the donor ceremony, she announced that she would step down in the summer of 2020. The time had come for “Prep’s next chapter,” she said, in a statement, and for her “to explore life outside of Prep.” I spoke with her shortly after her announcement, and asked what that next chapter might be. She reiterated the value of Prep’s current mission. “Not so long ago, people were thinking about, you know, have we reached a post-racial society,” she said. “And I think that in the last couple of years people are saying, ‘Now, more than ever, Prep for Prep’s work is vital.’ ” The board’s search for a new chief executive, led by the firm Spencer Stuart, is under way.
In January, I called Joseph at his office in Brooklyn, to ask what he thought of Prep’s future. He’d said in his speech that “Prep’s mission has never been about just getting us into private school,” and I asked him to elaborate. “We got really good at this one thing, and that became who we are,” he said. “Companies that get really good at one thing tend to fall off the face of the earth when they don’t change with the times.” Maybe the organization could begin to branch out—by, say, selling Prep’s curriculum to failing school districts and helping them to implement it. Prep, he seemed to be saying, was too small: the organization needed to help more kids, even if it did so in different ways. Perhaps it could reach beyond New York, and perhaps it could reach those who aren’t scooped up in its talent search. It’s not enough to promote a “talented tenth,” Joseph said, referring to W. E. B. DuBois’s notion that “the Negro race, like all races, is going to be saved by its exceptional men.” He added, “Our success alone does not open any doors.”
Forty years after the 1968 strike, the middle school where it began, J.H.S. 271, was closed by Bloomberg, for poor performance. The building is now home to three separate schools, including the Ocean Hill Collegiate Charter School. During Bloomberg’s tenure, New York’s graduation rates improved, but segregation deepened—the city’s public schools are as segregated now as they were under John Lindsay. In the interim, millions of black children have passed through the system, some served well enough, others hardly at all, none of them ever able to simply assume that the education offered to them by their government would prepare them for the wider world. (A school-desegregation plan that includes a proposal to abolish “gifted” education is being considered under New York’s current mayor, the liberal Democrat Bill de Blasio.)
We are all embedded within systems, but each life—each child—is an unrepeatable anecdote. According to the adults I knew when I was a kid, the worst thing in the world was to be a “statistic,” subsumed into a mass of low expectations and bad outcomes determined by color and class and sustained by a bureaucracy that was, at best, inept and, at worst, intractably racist. Education, then, was triage; escape was a higher-order concern than reform. Parents murmured about how So-and-So had got her daughter into Such-and-Such school, and had spirited the kid away from a school system whose failures symbolized—and, in many ways, flowed out of—a larger set of brutal social facts.
Before her announcement, I asked Hefferren whether Prep, by its nature, helps to keep broader inequalities intact. “We’re going to help create principals, superintendents, education commissioners—people who are going to really change that system,” she said. Among Prep graduates, education is the second-most-popular field of work. Is it their—is it our—responsibility to change the system now? Are we succeeding? When I spoke with Nikole Hannah-Jones, she criticized Prep’s philosophical orientation, but also told me that she does not begrudge the choice some black parents make to send their kids to such programs. “The onus of fixing the system” should not fall on them, she said.
I thought of conversations I’d had over the years with all the Prep alums I know, about what the program had and hadn’t done. One friend, a fellow Horace Mann graduate and a son of Nigerian immigrants, who now lives in Amsterdam and is perpetually astonished at the thick web of public services there, told me, over dinner near his home, “If Gary Simons had devoted his life to single-handedly turning around the whole system, he’d have died (a) sooner and (b) without having changed that much.” And here we were, two kids from nothing much, gently arguing over dinner at a bistro across the ocean from where we grew up. Another alum pointed out to me, at a birthday party, that her son was only a generation removed from the material want she had known, and two generations from the Haiti her parents had left. Yes, it would be good for well-off people to send their kids to public schools, she thought. But, no, she couldn’t afford for the “experiment” to start with her son.
To be educated is to be subject to a series of experiments. When Simons was planning the lessons for Aspects of Leadership, he considered adding a section focussed specifically on politics, which would have been reserved for the students who had taken most ardently to the curriculum. These superbly trained young people could go on, he thought, to fix the society-wide problems that had made Prep necessary. The course was never implemented at Prep, but Simons later incorporated it into leda. Simons remains a close observer of national politics: on an e-mail list and a blog that he updates more than once a day, he regularly shares thoughts in support of his preferred 2020 Presidential candidate, the unusually bookish thirty-eight-year-old Pete Buttigieg, a graduate of Harvard and Oxford.
In January, I attended an open forum of Prep alumni, held by the search committee that will choose the program’s new chief executive later this year. There was a nervous mood in the room, less about the future leader than about the existential issues that the change represented. What, exactly, made Prep different from other similar programs? And now that private schools, on their own, without nonprofit intervention, seek out nonwhite students, starting in kindergarten—often from affluent families—what exactly was the program’s role?
Prep has more than three thousand alums now, many of whom are in their forties and early fifties, with their own children to agonize over. One of them, a father of two, spoke up. “All of us have to make that decision,” he said. “Am I going to send my kids to the same place I went to?” It was one in a series of rhetorical questions. The representative from the search committee wrote it down. ♦
