With his charcoal gray suit on a mild April night in the West Village, Norman Siegel is wearing tan work boots. Perhaps it’s because he has come to the LGBT Community Center on West 13th Street to talk about putting boots on the ground.

If he were the city’s public advocate, Siegel tells the Gay and Lesbian Independent Democrats, he’d recruit a handful of volunteers in every neighborhood in the city to report problems and serve as shock troops when it’s time to fight an urgent problem like the mayor and City Council trying to extend term limits. “If people tried to do these kinds of things, we’d have a thousand people on the ground within 24 hours,” says Siegel. “We need a civil rights, social justice mindset in the public advocate’s office,” he tells the crowd. “It’s the only office where you represent the people against the government.”

Well-known for a lifetime of challenging government, Siegel is seeking for the third time to be part of it. Eight years ago he eked out a second-place finish in a seven-candidate Democratic primary for public advocate, besting three rivals who had more money—not a bad showing for a noted civil libertarian in the immediate post-September 11th era. But Betsy Gotbaum soundly defeated him in that year’s runoff. In 2005, the incumbent Gotbaum took 49 percent, to Siegel’s 30 percent, in a three-way primary.

This time will be different, Siegel says. Though presently trailing his three rivals in the Sept. 15 Democratic primary in fundraising, he’s second in the polls behind former Public Advocate Mark Green, and ahead of City Council members Bill de Blasio of Brooklyn and Eric Gioia of Queens. And Siegel says he’s more comfortable with life as a politician now—including the art of boiling his whole philosophy down to a three- to five-minute stump speech. “I’m getting a much better reception. The fact that I’m still trying to be public advocate resonates with people,” he says. “They say ‘You must really want the job.'”

Siegel wants the job badly—because, he says, his skill set is perfect for it. He’s been fighting against government for New Yorkers’ rights for years. Of course, it’s that very reputation for yelling truth to power that undermined his earlier candidacies. “There is no evidence,” wrote the Times editorial page in 2001, “that Mr. Siegel has any arrows in his quiver besides the press conference and the lawsuit.” In 2005, Gotbaum charged in a debate that Siegel was “running for public adversary instead of public advocate.”

Few if any New York City candidates have won citywide office on their third try. But Siegel is not dissuaded. “It’s good to be smart, but what’s more important?” he tells the crowd in the Village. “Stamina. Outlast the bastards.”

Opening arguments

In his law office, where surfaces are stacked chest-high with documents that don’t fit in the filing cabinets, the 65-year-old Siegel points to a picture of a much younger version of himself talking to Supreme Court Justice William O. Douglas, who in 1973 was the lone justice in the Holtzman v. Schlesinger case to side with Siegel’s argument that the bombing of Cambodia was illegal.

That was a big fight, but not his first. Siegel was raised in Brooklyn, attended Brooklyn College and NYU Law School and then in 1968 joined an ACLU project that aimed to end the exclusion of blacks from Southern jury pools. Next, in 1972, he ran an effort to register young voters made eligible by the new 26th Amendment – which set the voting age at 18 – before joining the New York Civil Liberties Union in 1973 as a field director, where he pushed for the impeachment of President Nixon and worked on the Cambodia case. He became the director of MFY Legal Services, a law firm for poor people, in 1978. In that role, for the next seven years Siegel spoke out on issues like affordable housing and welfare policy.

In 1985, he rejoined the NYCLU as executive director and became a regular presence in arguments over city policies, from drug testing of prison guards and teachers, to whether fans at Yankee Stadium could display signs criticizing George Steinbrenner. He spoke out on police shootings, a ban on flag burning, evictions of drug dealers, school uniforms, restrictions on condom distribution, desegregation in Yonkers and zoning rules that threatened topless bars.

The work often put him in conflict with the city’s chief executive. When Mayor Ed Koch began forcing mentally ill homeless people from the streets into treatment, Siegel told reporters: ‘We are going to have to go out one night at a time and tell them that they don’t have to worry about being taken away.” After Mayor David Dinkins said that “brothers and sisters” were on his side over his handling of the 1991 Crown Heights riots, Siegel denounced the mayor’s reference to his black political base as “extremely troubling, divisive and demagogic.” And Siegel cried foul when Mayor Rudy Giuliani wanted to issue tax-exempt government bonds to finance parochial school construction, bar AIDS protesters from City Hall, prevent a Million Youth March in Harlem or stop taxi drivers from demonstrating.

The people Siegel fought for were not always the most savory. Siegel came out swinging for a mob lawyer held in contempt for remarks to the press, said disgraced financier Michael Milken was unfairly sentenced, and contended that the Ku Klux Klan had a right to march wearing masks. Siegel said militant Muslims must be allowed to use school property for events, and that city inmates had a right to use a telephone (amid widespread calls for the phones to be ripped out of Rikers after a cop was killed on orders from an imprisoned man). He supported a police officer who wore blackface while marching in an off-duty parade. And sometimes his positions put him at odds with the liberal activists who usually cheered his work, as when he criticized anti-tobacco rules and supported the right of St. Patrick’s Day parade organizers to bar gay and lesbian groups from marching (he also supported the right of an alternative, gay-friendly march to get a parade permit).

This was Siegel’s public face. Back at the NYCLU office, he was the manager of a large and initially debt-saddled nonprofit. Siegel scrambled to find funds and spend them wisely, resulting in ruffled feathers along the way. “Inevitably with the financial crisis, there were strains,” says Donald Shaffer, an attorney who worked at the NYCLU during Siegel’s time there and once disagreed with him so starkly on a question of tactics that it went to the Union’s board. Siegel lost the vote, then congratulated Shaffer on a fight well fought. The NYCLU returned to fiscal health during Siegel’s watch, Shaffer says.

Although Siegel weighed in on myriad issues, the NYCLU’s resource constraints meant it could take up only a few cases at a time. Shaffer says a lawsuit NYCLU filed over funding inequities for low-performing school districts outside the city reflected Siegel’s approach. “[The case] was institutional—it involved more than one person. There were foundations willing to provide support. And there was a political element,” in the grassroots support that the case could mobilize, Shaffer recalls. Under Siegel, Shaffer says, there was a shift from the NYLCU’s traditional, exclusive focus on the first amendment to more work on equal protection cases. Also, Shaffer says, “There was a general proposition that we should try frontier issues.”

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