But for thousands of families in Harlem, the ones who flock to her Success Academies and swell her lottery wait-lists, Moskowitz is a paladin in earth-toned suits. They back her en masse at every showdown, from City Hall to Albany. “We love what they’re doing with our kids, and so we’ll fight the fight whenever she needs us,” said Sherry Cayson at a city hearing last spring, when Moskowitz railed against the “union-political-educational complex.” Cayson’s first-grader reads 35 books a month, gets tutored whenever he needs it. “Where else are we going to get this quality of education—for free? Where are we going to put our babies?”
Moskowitz has lived in this storm since her maiden run for the City Council in 1997, as a silk-stocking-district Democrat with all the correct leanings (Amnesty International, Sierra Club, NARAL), save for one: her conviction that New York’s public schools were “tenth-rate.” Her star rose when she allied with Gifford Miller, who became speaker in 2002 and made Moskowitz the chair of the long-somnolent education committee. Over the next three years, she staged more than 100 oversight hearings—a smaller-scale Watergate, her childhood fixation. She grilled and filleted bureaucrats from the DoE on their sickly science and art programs, the back-of-the-bus Regents-diploma rates for minority students, the pervasive shortage of toilet paper in what was then a $13 billion–a–year operation. (Among thorns in his side from that era, Klein pegged Moskowitz “up there in the top five, or the top three.”)
In 2003, she torched the teachers union with hearings on seniority rights and work rules. Most everyone—even her husband—warned her that she’d be “squashed like an ant.” The proceedings, complete with hidden witnesses using voice-distortion technology, were explosive. Newsweek hailed the councilwoman as “a brave New Yorker”; UFT president Randi Weingarten likened her to Joseph McCarthy. Yet Moskowitz seemed unaware of her own polarizing impact. Two years later, she was devastated when the Times labeled her style “abrasive” and joined the UFT in endorsing Scott Stringer for Manhattan borough president, her stepping-stone toward Gracie Mansion. Stringer beat her by nine points, but it’s the adjective that still flusters her. “I’m a fierce advocate—which doesn’t mean one is abrasive,” she says.
“She could have been borough president,” says a former UFT official. “But she’s a purist. Sometimes, to me, she’s very naïve.”
The work-rule hearings kindled her epiphany: An unholy “conspiracy” between the UFT and the Department of Education had deprofessionalized teachers, hamstrung principals, and sabotaged countless students’ futures. Charter schools, uninhibited by “special interests,” were the Way. All they needed was a chance to compete, a free market. At a Crain’s breakfast, Moskowitz scolded the deep pockets in attendance for failing “to declare war on the monopoly of public education … Your silence is inexcusable.”
The day after leaving office, she set to work for Joel Greenblatt and John Petry of Gotham Capital, her network’s founding funders. Dug in at a Starbucks with a cadre of aides, she put to paper her philosophy: one part Bank Street (the liberal education college), one part Our Lady of the Assumption. She’d spent “six years thinking deeply about what the DoE was getting wrong,” as she’d tell the New York Sun. “This was an incredible opportunity to get it right the first time.”
At five-two, Moskowitz perches easily on a chair made for a 6-year-old, her BlackBerry and cell phone fanned before her, a triple-shot latte close at hand. She is weary; she is always weary. “Why doesn’t anyone care that the schools in Harlem have been unsuccessful for half a century?” She speaks slowly, emphatically. “Why is this not a big deal? To me, it’s a terrible deal.” Her pink-tipped fingers cleave the air. “We’re a caring city, right? Where is the intelligentsia on this issue? Where are the civic-minded people?”
Two generations removed from a sweater peddler on the Lower East Side, Moskowitz was raised by a pair of liberal college professors and lived for ten years in Columbia housing on West 118th Street. In first grade at P.S. 36, she saw “perfectly capable” classmates unable to read, with no one paying much attention. It was her first intimation “that the system is screwed up,” a suspicion that hardened after she was switched to P.S. 6 on the Upper East Side. Even at age 7, she says, “you can see what you’re not getting.”
She slogged her way to the city’s crown jewel, Stuyvesant High School, only to find it rotted from within. During her sophomore year, a scandal broke over stolen Regents exams. “There was a culture of cheating,” she says. After the proctor left the room during the PSATs and a collaborative free-for-all ensued, Moskowitz stood and quit the test midstream. A year or so later, while editing the yearbook, she was appalled to find photos that revealed more cheating—and disgusted when the principal seized them to cover it up.