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 mo-
ment 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 academi-
cally—almost disruptively so. The teach-
ers eventually put them in a separate read-
ing group. “And then, when we got to a
certain point with the three of them,” Si-
mons 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 arm-
fuls of flowers from the garden of a house
he’d spent the day painting on Long Is-
land. 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, Si-
mons was going regularly to the boy’s
house to tutor him. The kid sped through
the lessons for advanced second grad-
ers, and was ready for third-grade read-
ing, 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 stu-
dents were given reading that was sev-
eral levels below where they’d left off,
on the assumption that low-income kids
inevitably slid backward over the sum-
mer. Simons was furious—he resolved
to make extra efforts on behalf of hisespecially 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 admis-
sions and financial-aid officers that the
children would fit right in at their ex-
clusive institutions. Among these stu-
dents was a son of Puerto Rican immi-
grants 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 tal-
ents—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 tal-
ent as a top priority, but a few younger
admissions officials and school heads,
shaped politically by the civil-rights move-
ment, were immediately on board. The
plan that Simons had outlined for Prep
for Prep echoed the approach of A Bet-
ter Chance, a national organization that
was founded in 1963 to help poor black
students and now focusses on ethnic di-
versity without attention to income. (No-
table alums include the recent Presiden-
tial candidate Deval Patrick and the
singer-songwriter Tracy Chapman.)
These administrators were part of a van-
guard that would eventually establish di-
versity of this sort—the simple fact of
more nonwhite faces in a room—as a
preoccupation of their profession.
Simons knew nothing about man-
agement, or what it would take to raise
money from wealthy people for an an-
nual 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 Mi-