64 THENEWYORKER, MARCH 9, 2020
Podcast.” He now works as a server at
a restaurant in Greenwich Village.
“My real question to Aileen,” he ex-
plained, “was: How are you going to
protect the psychologies of these kids?”
A
few years ago, the sociologist An-
thony Abraham Jack conducted a
study of the experiences of undergrad-
uates of color from low-income back-
grounds who attend élite private col-
leges. Drawing from nationwide data
and his own research, he found that half
of these students are graduates of pri-
vate 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 usu-
ally an up-from-nothing story. What is
more common, in the relatively rare in-
stances of mobility which our society
currently provides, is a series of institu-
tional incursions, which lend a kind of
jerry-rigged privilege to a chosen few.
Ed Boland worked in Yale’s admis-
sions 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 Ameri-
can name, and worked at a soup kitchen
in France, and had internships at their
father’s bank,” he said. “These experi-
ences are how we have shaped our lead-
ership class for a very long time.” He
went on, “But, on this particular after-
noon 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 demand-
ing schools but also signify a kind of so-
cial standing. “Prep for Prep is like a
stimulus package for an individual,” Jack
told me. My friends often joke that, in-
stead of a rich parent or a working so-
cial 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 Mid-
west and San Francisco. They wore Pa-
tagonia 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 Middle-
bury students who came from New York
had attended segregated public high
schools in Harlem and the outer bor-
oughs. A few had applied to Middle-
bury 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 tostart, I couldn’t will myself to go. Maybe
I was feeling squeamish about the blood
and shit that my interviewer, a kind-look-
ing black woman, had taken pains to in-
form 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 some-
thing like suspicion, but also with some-
thing 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 differ-
ent path from this one. Keep going.”
My daughter was born in the fall of
2005, when I should’ve been a college se-
nior. 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 up-
ward, squinching his forehead into folds.
In the summers between school years at
Middlebury, I’d worked as a teaching as-
sistant 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 bro-
ken up a fight? Had a kid curse at you?”
It is an odd feeling to watch your-
self 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 some-
day supposed to belong. I felt like what
I was: young, black, jobless, an unmar-
ried father. I wanted to tell those inter-
viewers 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 invest-
ment banker who was on Prep’s board
of directors. The banker paid me di-