66 THENEWYORKER, MARCH 9, 2020
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-lan-
guage training, and then have them start
the preparatory component,” Bordo-
naro said. These days, I noted, a program
like that would register as a fairly un-
subtle rebuke of the Trump Adminis-
tration. 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 ad-
mission to prestigious colleges. The pro-
gram 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, be-
cause of medical problems.)
Hefferren was, in some ways, an ob-
vious choice to replace Simons at Prep.
She knew the program well and had
an extensive background in fund-rais-
ing. The educational landscape in New
York was shifting: the year that Heffer-
ren took over Prep, Bloomberg was
elected mayor, and assumed unprece-dented 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 pub-
lic schools can. They can also, crucially,
craft their own curricula. Some of the
donor money that once flowed to Prep
began drifting toward those institu-
tions. Philanthropists tend to swim in
tight schools, often under the influence
of a small group of paid charitable ad-
visers. 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.’” P r e p’s
budget is now thirteen million dollars;
its partner schools offer more than thir-
ty-five million dollars in financial aid
to Prep students annually.
This past fall, Leslie-Bernard Jo-
seph—whom I’d seen talk, a year before,
with Hefferren at the Schomburg Cen-
ter—received Prep’s annual Alumni Prize.
He accepted the award at a private cer-
emony for generous donors, and took
the opportunity to make an announce-
ment. “Prep cannot say with integrity
that it fulfills its mission until it has di-
verse 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 reiter-
ated the value of Prep’s current mis-
sion. “Not so long ago, people were
thinking about, you know, have we
reached a post-racial society,” she said.“Will my tone come off as mean if I don’t use an exclamation mark?”