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Jamie (Maggie Gyllenhaal), Jay Lefkowitz, and Nona (Viola Davis) are pleased with their plans to transform their children’s failing inner city school. (Photoillustration Tablet Magazine; original photo Kerry Hayes/Walden Media and Jung Yeon-Je/AFP/Getty Images)

The new 20th Century Fox movie Won’t Back Down—starring Maggie Gyllenhaal and Viola Davis as a parent-teacher duo that confronts a corrupt teachers’ union in their attempt to take over a failing Pittsburgh public school—is a fictionalized version of actual events in California, where several groups of poor, minority parents have faced off against unions and their allies. But one character you won’t meet in the movie is a key figure from the real-life drama: an Orthodox Jewish political hand named Jay Lefkowitz who heads the group of pro-bono lawyers advocating for the parents.

A veteran of both the George H.W. and George W. Bush White Houses, Lefkowitz has been at the forefront of school-choice efforts for two decades, first as a domestic-policy adviser and then as a litigator handling school-voucher cases in Wisconsin and Florida in the 1990s. In the years since, what began as a conservative cause has, through the rise of the charter-school movement, morphed into an issue that many progressives have embraced, believing that the market model can be used to push for faster and more effective change in public education for those at the bottom of the ladder.

But like their predecessors on the right, this new generation of reformers—including former District of Columbia Schools Chancellor Michelle Rhee and former Clinton White House operative Ben Austin—has run into fierce opposition from teachers’ unions. They’re relying on battle-hardened warriors like Lefkowitz to keep judges on their side. “We’re the rabble-rousers and troublemakers, but it’s the court battles that make the difference,” Campbell Brown, the former CNN anchor who has recently gotten involved in education reform issues, told me. (She hosted screenings of Won’t Back Down at both the Republican and Democratic national conventions this summer.) “If Jay wins, it’s a big deal.”

Lefkowitz is currently fighting on several fronts. Along with partners in the Los Angeles office of his firm, Kirkland & Ellis, he is trying to help parents in the exurban community of Adelanto, Calif., on the western edge of the Mojave Desert, become the first to successfully pull the so-called “parent trigger” dramatized in Won’t Back Down—a petition right afforded to parents in schools rated as failing to either replace existing staff or convert the school into a charter. In New York, he is representing nonprofit charter operators seeking to open in existing city school facilities, and in Newark, N.J., Lefkowitz has gone to court on behalf of virtual charter schools, part of a broader effort by Newark Mayor Cory Booker to expand charter schools in the city.

“These cases are very far away from the earlier cases, because they don’t primarily involve federal or constitutional issues, and they don’t bring up establishment or free exercise of religion claims,” Lefkowitz told me when we met for breakfast earlier this week at the Loews Regency Hotel in Manhattan. “But they are cases where the status quo is being challenged.” That’s why, he said, he’s been willing to make almost weekly court appearances in New Jersey and wrangles his partners into devoting countless hours pro bono to these cases.

Lefkowitz remains unapologetic about the conservative ideological roots of the current school-choice wars. “All education reform is about creating competition,” he insisted. In Wisconsin, he said, public schools responded with tutoring once vouchers gave parents the wherewithal to choose private or parochial options. Charter schools, coupled with the determination of newly empowered school chancellors like New York City’s former schools head Joel Klein to shut down failing schools, could similarly force public teachers and administrators to step up, Lefkowitz argued. “You have to reinvigorate the public schools,” he added. “And you have to have a ground game, because ultimately what you’re talking about is changing the way local government operates.”

Lefkowitz makes an unlikely culture warrior. At 49, he is slightly baby-faced, with sandy hair and blue eyes behind thin-rimmed glasses. He grew up in what he describes as “a real neoconservative family”—though his father, Jerome, a labor lawyer who drafted New York’s landmark Taylor Law and who still chairs the state’s Public Employment Relations Board in Albany, told me he supported the Progressive candidate Henry Wallace in 1948 because people wearing Wallace buttons dropped the most generous contributions into the Jewish National Fund pushkes he carried on the subway as a teenager. “A large number of them contributed dollar bills rather than coins,” the senior Lefkowitz recalled. “That made an impression on me.”

Jay Lefkowitz’s mother, Myrna, taught Hebrew, and Lefkowitz graduated from a Jewish high school with seven students before going on to Columbia University for both his undergraduate and law degrees. As a young White House staffer handling domestic policy in the administration of George H.W. Bush, he worked with Tommy Thompson, then governor of Wisconsin, and Lamar Alexander, then Bush’s education secretary, who conceived the first school voucher programs. “It was cutting-edge public policy reform,” Lefkowitz told me. “And as a lawyer, it was all about the constitutionality of the vouchers.”

With Congress still years away from Newt Gingrich’s Republican Revolution, Lefkowitz’s job from his West Wing perch was to help ideological allies like Thompson push reforms at the state level. “I was a strong proponent of vouchers, from an education perspective, but I was also committed to them as a committed Jew who believes Jewish education is absolutely necessary for Jewish continuity,” said Lefkowitz, who sent his three children to Ramaz, the Modern Orthodox school in Manhattan.

After leaving the White House, he joined Kirkland & Ellis, where he and his former Bush Administration colleague Ken Starr were drafted into helping Thompson defend the constitutionality of a voucher program in Milwaukee. Lefkowitz eventually won the case in oral arguments before the state’s Supreme Court. “Starr was in the middle of the inquiry about Monica Lewinsky, so he sent this great understated letter saying he was otherwise occupied,” Bob Chanin, who argued the opposing side as the longtime counsel for the National Education Association, which represents teachers’ unions, told me.

In 2002, the Supreme Court ruled in favor of a different voucher program in Cleveland, allowing parents to use public money to pay for parochial schools, but efforts to expand voucher programs stalled nationwide. Meantime, the popularity of charter schools—first established in Minnesota in 1991 and widely seen as a way to open up educational options within the context of the public-school system—rose, the wheels greased in part by a 2001 decision by the National Education Association not to oppose charter schools wholesale. “In the early 2000s, we had pure Democratic support opposing vouchers, but that came at a price, because they said, ‘Give us something we can support,’ ” Chanin explained. “And that was charter schools.”

But charter schools are far from a universal alternative to troubled public schools, which is what led Ben Austin, the former Clinton staffer, to launch Parent Revolution, a nonprofit aimed at helping parents push for reform in their schools, in 2008. “Fundamentally, we want to make public schools more public by being more accountable to the parents and children they serve,” Austin told me. “The only way we’re going to get there is to affect an unapologetic transfer of power from the status quo to parents.” In 2010, Austin helped draft California’s parent trigger law, which in theory allows parents to turn their schools over to charter operators—even over the opposition of elected school boards.

This has prompted charges from some that the trigger turns parents into agents for expansion-minded charter school operators. “It raises the question of who owns the public schools,” said Diane Ravitch, a professor of education at New York University and longtime proponent of public education. “Do users of a facility own the facility? Suppose tenants of a housing project vote to take over the project and give it to a private developer. Should prisoners be able to take control of a jail? Or people riding in a public bus, who decide the driver is crummy? They don’t own the bus because they’re riding on the bus.”

Nevertheless, the parent trigger concept has already spread to six states beyond California. In June, it was endorsed by the national Conference of Mayors; politicians including Booker of Newark, former Obama Chief of Staff Rahm Emanuel in Chicago, and Antonio Villaraigosa, the Democratic mayor of Los Angeles, have been vocal proponents of the measure. Last month, a Gallup poll found 70 percent support for trigger laws.

But the California law has yet to be successfully applied. In 2010, Parent Revolution organized parents in the Los Angeles neighborhood of Compton to try and take over McKinley Elementary, which was ranked in the bottom of 10 percent of schools statewide. Lefkowitz read a Wall Street Journal feature about it and decided to get involved. “I said, ‘These guys are fantastic, but they are going to get clobbered,’ ” Lefkowitz told me. He called to offer Kirkland’s services and brought in Mark Holscher, a partner in the Los Angeles office, to handle the day-to-day aspects of the Compton takeover effort, which ultimately failed after parent petitions were declared invalid on technical grounds.

“The two people without whom there would be no parent trigger laws are Jay Lefkowitz and Barack Obama,” Austin said. “Parent trigger passed as a direct result of Obama’s Race to the Top, and right after that we found ourselves embroiled in the quagmire with Compton Unified. So, if Jay hadn’t called us, I don’t know where we’d be.”

Now Lefkowitz is looking for definitive victory at the Desert Trails elementary school in Adelanto—one that could help translate the chatter around Won’t Back Down into results. The movie’s producers, Walden Media, which backed the 2010 pro-charter school documentary Waiting for ‘Superman,’ already have a website dedicated to spurring parent activism, but Lefkowitz wants to offer a concrete example. “A movie like this has the capacity to bring the issue to a broader public,” Lefkowitz said, “but you need court battles to validate it.”

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