THENEWYORKER, MARCH 9, 2020 61
ple 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, Guer-
rero became one of Prep’s longest-serv-
ing employees. He’s now the director of
admissions at his alma mater, the Eth-
ical 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 typewrit-
ten 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,” “eth-
ics,” and “tactics” of leaders, focussing on
the difficulties inherent in a pluralistic
democracy. This curriculum, called As-
pects of Leadership, began with a few
specially selected students but soon be-
came 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 infor-
mally 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 eth-
ics 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 ar-
ticulate—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 psy-
chic 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 re-
called saying to parents. “That whatever
obstacles remain”—racial, social, eco-
nomic—“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 indi-
vidual ability of a handful of students is
a fundamental flaw in the program’s de-
sign. Nikole Hannah-Jones, the Times
journalist who created the 1619 Project—
which marked the four-hundredth an-
niversary 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 pro-
grams 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 al-
lows us to sustain all the other inequal-
ity 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 Wash-
ington 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 work-
ings 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 lead-
ership programming and who was the
only white person in the room. I couldn’t
help but imagine Simons rolling his eyes.P
rep was built atop a fault line of
American education. In 1778, shortly
before he became the governor of Vir-
ginia, Thomas Jefferson drafted A Bill
for the More General Diffusion ofKnowledge. In Jefferson’s vision, all the
free boys and girls in the state would
spend three tuition-free years learning
“reading, writing, and common arith-
metick” and becoming “acquainted with
Græcian, Roman, English, and Ameri-
can 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 dis-
position” 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” move-
ment gathered momentum, in the eigh-
teen-thirties and forties, that public ed-
ucation began, gradually, to take hold.
The movement’s ideals were most fa-
mously promulgated by the Massachu-
setts reformer Horace Mann, who be-
lieved that education could be “the great
equalizer of the conditions of men.”
When Teachers College was estab-
lished, in 1887, it created an experimental
school, and named it for Horace Mann.
It is now a notoriously exclusive prepara-
tory school that sits on a grassy campus
overlooking Van Cortlandt Park, in Riv-
erdale. 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 head-
master 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 di-
rector 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