60 THENEWYORKER,MARCH9, 2020
I can trace back to the program. The
change isn’t only personal. No matter
the context, certain privileges accom-
pany being thought smart: teachers kin-
dle 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.
T
here were criticisms of Prep’s meth-
ods from the beginning. People asked
Simons whether it was wrong, in a sys-
tem marred by disparity, to focus on stu-
dents already advantaged by their intel-
ligence. This concern made him livid, he
told me. “It is precisely these kids who
are losing the most, because of the differ-
ence 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 hap-
pening all over the country. “He thought,
in some cases, that we were producing
very gifted criminals,” Lester, the Trin-
ity headmaster, told me. Simons studied
at Teachers College under Abe Tannen-
baum, 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 pro-
gram, in the mid-nineties, Simons had
more or less acclimated to life as a non-
profit 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 cre-
ated the Lilac Ball, an annual ceremony
for Prep students who have been ac-
cepted to college. The event doubled as
a large fund-raising gala, and quickly
became a fixture on New York’s philan-
thropic 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 men-
tors to guide younger kids through the
first summer, making life easier for new-
bies and insuring a loyal and motivated
body of alumni. To lead the effort, Si-
mons 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 stu-
dents from underserved New York City
communities for success at top indepen-
dent 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- An economy was growing, and its
chief product, smart black and brown
kids, was increasingly visible, if still de-
cidedly 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 gov-
ernment at their schools. “I began to
realize that although, initially, my in-
tention 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 poten-
tially, like, national treasures. And not to
have their potential developed is a loss
to everyone else.” He decided that Prep
would become a “leadership develop-
ment” 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 de-
servedly so—that they only pushed peo-
The students take courses in writing, history, science, math, and, usually, Latin.