THE NEXT CHAPTER

Education / Founders / New York

Eva Moskowitz and the Trouble With Good Enough

She spent six years asking New York’s school system difficult questions. Then Eva Moskowitz opened a school of her own - and inherited a different set of questions.

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Eva Moskowitz once held a hearing about toilet paper. This was during her years on New York’s City Council, when she was examining a school system with a multibillion-dollar budget and asking why its bathrooms could still lack the essentials. Education reform generally prefers a grander opening sentence. Moskowitz was prepared to begin in the lavatory.

The detail matters because it makes her career easier to understand. She approaches schooling as a collection of decisions adults make, then sometimes cease to notice: what gets ordered, what gets taught, what a contract permits, what happens when somebody makes a promise and nobody returns to check. Her questions tend to arrive with follow-up questions attached.

During her council years, she would reread the transcript before the next hearing. Officials would change jobs; commitments would disappear into the institutional furniture. She brought the old promises back. An assurance about arts teachers could therefore acquire an awkward second life. Bureaucracies have many survival skills. Being reminded of their own sentences is rarely their favorite.

Twenty years after opening the first Success Academy in Harlem, she leads a network that reported 59 schools and 22,000 students in 2026. Her career has become a sustained argument about what adults owe children. It has also made her responsible for answering the kind of uncomfortable questions she once asked from the other side of the table.

The child who had another classroom at home

Moskowitz was born in New York in 1964 and grew up in Harlem. Her father was a mathematician; her mother was an art historian. At home, learning had the advantage of two resident enthusiasts. At school, she remembers a rather different intellectual pace.

She has described attending P.S. 36 and spending months revisiting mathematics she already knew. Her parents could fill the gaps at home. She understood that many classmates depended entirely on what the school provided. Her account of that difference is the seed of her later argument: a child’s opportunities should not depend on having an alternative education waiting after dismissal.

She eventually attended P.S. 6 and Stuyvesant High School. As a teenager, she volunteered to help Cambodian refugee families find apartments. She recalls persuading a reluctant landlord to accept a family by appealing to the country’s immigrant history. It was an early experience of discovering that an objection could be argued with.

History became her academic field. She graduated from the University of Pennsylvania in 1986 and completed a doctorate in American history at Johns Hopkins in 1991. Before becoming a school founder, she taught at universities including Virginia, Vanderbilt, and the City University of New York. She also taught civics at Prep for Prep. The route to the principal’s office involved a considerable amount of homework.

After the hearings, a school

Elected to the City Council in 1999, Moskowitz represented Manhattan’s East Side and chaired its Education Committee. She visited schools and challenged the arrangements governing them. Union contracts, curriculum, supplies: she treated the machinery of education as something an elected official was entitled to inspect.

That put a Democrat in conflict with an institution closely associated with Democratic politics. In 2005, she ran for Manhattan borough president and lost to Scott Stringer. Opposition from the teachers’ union was part of that contest. Her next job offered a different kind of authority, along with the inconvenience of being directly responsible for the result.

Investors Joel Greenblatt and John Petry had been pursuing a charter-school project and recruited her to lead it. In 2006, the first Harlem Success Academy opened with 165 kindergarten and first-grade students. The venture carried a replication plan from the start. One functioning school would be useful; a network might make a larger argument.

A charter school is publicly funded and independently operated under a charter. Success Academy’s admissions use a public lottery. Families do not pay tuition. Those features are essential to Moskowitz’s proposition: an education with ambitious expectations should be available to families who cannot buy their way into a different school.

A school becomes a network
2006
1 school
2026
59 schools
165children at opening
22,000students reported in 2026
Twenty years between the first Harlem classroom and a network spanning New York City. Bars compare school counts; student figures are separate.

The warehouse has entered the argument

The difficulty, of course, is that a school network needs its own machinery. In 2015, a supplies and furniture problem threatened the opening of Success Academy schools. Staff went to a Long Island warehouse to sort and dispatch materials, working evenings and weekends. The schools opened with what they needed.

It was a revealing episode for a founder whose public criticism so often concerned bureaucratic failure. Growth had brought her organization an old-fashioned school-system problem: getting the right objects to the right buildings before the children arrived. Conviction could motivate the work. Somebody still had to pack the boxes.

She has argued that schools should correct mistakes immediately rather than postpone repairs until the next academic year. That instinct makes sense of both her urgency and the demands she places on colleagues. A year is a planning unit to an organization. To a child, it is a substantial piece of childhood.

The network’s public milestones give that urgency a visible result. In June 2025, it celebrated 217 graduates from two high schools. All had received four-year college acceptances, the eighth consecutive graduating year with that outcome. Acceptance is a milestone with a precise meaning; the longer work of attending and finishing college follows it.

“What I love about chess is it takes language off the table.”

Eva Moskowitz, 2016

High expectations, hard questions

The growth story includes serious disputes over how children experience the model. In 2015, a principal at Success Academy Fort Greene was found to have made a list of 16 students headed “Got to Go.” Critics saw evidence for a longstanding allegation that the network pushed challenging students toward the exit.

Moskowitz said the list violated the organization’s policy, described it as an anomaly, and took personal responsibility for what happened under her leadership. The principal apologized. Success Academy denied that removing students was its institutional strategy.

The following year, a video showed a teacher scolding a first grader and tearing the child’s paper. Moskowitz defended the teacher while acknowledging the incident; the teacher had been suspended and given additional training. Those episodes made the argument about standards painfully concrete. Parents were entitled to ask how a school’s ambitions translated into the treatment of an individual child.

Her political disagreements have been equally public. She battled Mayor Bill de Blasio over school space and prekindergarten oversight. In 2016, after meeting Donald Trump, she said she would not serve as education secretary. Her willingness to work across party lines has widened her alliances and complicated her standing with fellow Democrats. Agreement with Moskowitz on one subject has never guaranteed a quiet relationship on the next.

At home, the dice come out

There is another Moskowitz, familiar to readers of A+ Parenting, the 2023 book written with her husband, attorney Eric Grannis. Its subtitle promises a surprisingly fun route to raising smart children. The activities include board games, films, music, puzzles, and conversation. The household sounds competitive, but at least the competition comes with dice.

Moskowitz has described playing backgammon with her children as a way to encounter counting, probability, and eventually strategy. She and Grannis also listened to Bob Dylan and musical-theater recordings with them, stopping to discuss a lyric. A Sunday film could furnish the material for dinner-table disagreement. Interpretation was allowed to have a social life.

Her own parents had invited young children into adult conversations about public problems. She carried that expectation into raising three children herself. In a later podcast conversation, she described her adult children continuing to play games and recalled an eldest son competing in backgammon. The family pastime had survived the school years.

The private and public projects overlap in a consequential way: her two younger children attended Success Academy through high school. In a September 2026 essay, she revisited the uncertainty of enrolling her son before the young network had state test results. The founder asking families for trust also had to make a decision as a parent.

Eva Moskowitz smiling as her husband Eric Grannis kisses her cheek
A different kind of partnership meeting. Moskowitz and Eric Grannis, her husband and coauthor of A+ Parenting. Photograph: Eva Moskowitz author website.

Miami is the next examination

By 2026, Moskowitz’s work was moving beyond New York. Success Academy announced five Miami-Dade locations, with opening planned for the 2027-28 school year. The schools would begin with kindergarten and first grade in underused district facilities, then add a grade each year. The announced initial enrollment was 1,500 children across the five sites.

The Florida expansion had been unveiled in September 2025 alongside Governor Ron DeSantis and financier Ken Griffin, who pledged $50 million. It followed legislation easing the use of existing public-school facilities by qualifying charter operators. The welcome from state leaders contrasted with her battles in New York; objections about public resources and local control accompanied it.

Meanwhile, the New York arguments continued. In August 2026, Success Academy announced a federal lawsuit challenging the state’s decision not to authorize the release of Advanced Placement data for national school rankings. The network alleged that the omission obscured its students’ performance. A complaint states one side’s claims; a court must determine what follows from them.

In a July 2026 television interview, Moskowitz described her immediate ambition as national educational impact, with Miami potentially followed by other states. She wanted governors and mayors to see the model operating. The next stage of her career would test whether its routines, expectations, and organizational habits could travel.

The question that follows her

Her résumé offers several possible identities: historian, former politician, author, parent, chief executive. The continuity is her interest in what happens when an adult explanation meets a child’s actual day. A missing supply, an unkept promise, an uninspiring lesson: each becomes a decision somebody could revisit.

That habit has built institutions and generated conflict. It also establishes a demanding standard for her own organization. Every new school gives another group of families reason to expect that the promises will survive opening day, staff changes, and the temptation to declare the model finished.

The council member who brought yesterday’s transcript to tomorrow’s hearing now has a much larger set of promises to keep. Miami will supply new classrooms, new parents, and new questions. For a former historian with a habit of checking the record, there will be plenty to read.

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