Bill de Blasio attends a press conference outside United Nations Headquarters on Sept. 23, 2013, in New York City. At a media event held by the Jewish Community Relations Council of New York, he and other leaders spoke out urging the Iranian government to halt nuclear enrichment.(John Moore/Getty Images)

In late 1999, Hillary Clinton was photographed on a visit to the West Bank greeting Suha Arafat, wife of Palestinian leader Yasser Arafat, with a kiss. The incident quickly became fodder for attack ads by Jewish Republican groups in New York, where Clinton—then still first lady—was running to succeed Daniel Patrick Moynihan in the U.S. Senate. It fell to her campaign manager, a Democratic operative named Bill de Blasio, to do damage control.

De Blasio had years of experience dealing with the various ethnic factions that still make up New York City’s political power structure, first as an aide to former Mayor David Dinkins and then as a regional director for federal housing programs. His first call was to Rabbi Yitzchok Fleischer, the founder and executive director of Bikur Cholim D’Bobov, the aid organization of the ultra-Orthodox Bobover sect. They dealt with the Arafat business—though she never secured an outright endorsement, Clinton wound up doing well among ultra-Orthodox voters and won the Senate race in November 2000—and then turned their conversation to de Blasio’s career. Already a member of his school board in Brooklyn, de Blasio was planning to run for an open City Council seat in Brooklyn’s 39th District, which straddled liberal Park Slope and Borough Park, a stronghold of conservative ultra-Orthodoxy.

“‘I don’t want to go to Washington,’” Fleischer remembers de Blasio telling him. “‘I need your help.’”

Fleischer was more than happy to provide his support. A self-described socially conservative liberal Democrat, he convened a cabinet that met regularly in his living room, among other secret locations, as de Blasio’s campaign got under way in the wake of Clinton’s Senate victory. There was no reason to expect a lapsed Catholic who grew up in Cambridge—the so-called “People’s Republic”—to be at ease in the world of black hats and payot, and at first de Blasio wasn’t. But with Fleischer’s guidance, he spent the months before the 2001 City Council election working the midnight Borough Park synagogue circuit, a savvy bit of retail politicking that paid off in a crowded field whose presumed front-runner was Steven Banks, an attorney for the Legal Aid Society who, unlike de Blasio, was Jewish. De Blasio won the primary by 1,500 votes and never looked back.

As he’s made his way from the council to the public advocate’s office and now to his pole position as the presumptive successor to Michael Bloomberg as mayor of New York City, de Blasio has been helped along by a cadre of politically connected leaders in the ultra-Orthodox community who, like Fleischer, saw in the left-wing Ivy Leaguer with the Italian name someone they could work with. “This is a guy who’s as comfortable at a Shabbas tisch as he is at the Democratic National Convention,” says David G. Greenfield, the Orthodox city councilman who currently represents Midwood, Bensonhurst, and Borough Park.

In September, with Fleischer’s help, de Blasio won the endorsement of prominent members of Agudath Israel, the central organization of the ultra-Orthodox community, including the real-estate powerhouse Leon Goldenberg—a member of the recently formed Flatbush Jewish Community Coalition—and Shlomo Werdiger, a scion of the Gerer Hasidic dynasty. While leaders in Williamsburg’s Satmar Hasidic community backed former city Comptroller Bill Thompson, who had courted them assiduously, in the primary, de Blasio won by 15 points among Jewish voters citywide.

Of course, the rabbis of 13th Avenue are not tremendously enamored of de Blasio’s progressive social agenda, which includes plans to rein in the New York Police Department’s controversial stop and frisk program and perhaps even curb surveillance of Muslim citizens. But the Democratic frontrunner’s many yarmulke-wearing friends tend to think he’s a kindred spirit—practically a member of the tribe himself, they like to say—who has earned their trust, even if de Blasio’s biracial family and lack of outward personal religious faith place him firmly in a secular world far from theirs. Like most of New York City’s voters, they are eager to turn the page on the Bloomberg era, albeit for rather different reasons than the ones that have made de Blasio the object of liberal fascination nationwide.

“Whatever we needed, he was always there for us,” Fleischer told me, citing de Blasio’s support for childcare vouchers—a pet issue among the ultra-Orthodox, who send their children to private yeshivas—that were nixed by the Bloomberg Administration in 2010. And Fleischer, like many of the Orthodox elected officials and community leaders I spoke to, expects the door in a de Blasio City Hall to be wide open for him. “He owes me everything,” Fleischer said. “Without me he wouldn’t be anyplace.”

After his first council election, de Blasio tapped Rabbi Yeruchim Silber, an experienced fundraiser in Borough Park who was already volunteering for the campaign, to join his staff. Like Fleischer, Silber guided de Blasio through his synagogue visits and served as a validator within the community. He stayed on at de Blasio’s council office until 2005, when he was offered a new gig at the Metropolitan Jewish Health System. The two remain on warm terms: De Blasio attended one of Silber’s son’s weddings in 2007 and the sheva berachot for another son’s wedding just last year.

Since his election to the public advocate’s office in 2009, de Blasio has continued to lean on Orthodox counselors. He can sometimes be seen pacing around his offices with key Jewish advisers Avi Fink, who once ran Anthony Weiner’s congressional district office, and Pinny Ringel, a Hasidic operative who worked for Bloomberg’s re-election bids and has been involved in City Council races on both sides of the aisle. Fink and Ringel are seen as likely candidates for political jobs in a de Blasio Administration. (The campaign declined to make either of them available for interview.)

It doesn’t hurt that de Blasio has shown a willingness to overlook some of the Orthodox world’s more eccentric political preoccupations—among them, the defense of  metzitzah b’peh, a practice in which the mohel sucks blood from the circumcision wound during a bris. In September, de Blasio appeared to endorse a reversal of city policy limiting the practice, with video of him at a campaign event in the Satmar community being introduced as a candidate who supported the right of ultra-Orthodox groups to perform metzitzah b’peh “without compromise”—though a spokesman later walked his position back to one of working to “find a solution” that made both Jewish leaders and health regulators happy.

“This is a very important issue for the community, and we will discuss how to work it out the right way,” Fleischer said. No one really knows how many people observe the ritual, but it has become something of a political litmus test—and de Blasio’s willingness to appear open to revisiting Bloomberg’s directive requiring parents to sign a consent form detailing the health risks, considered an unacceptable incursion of the state into religious observance by many ultra-Orthodox leaders, speaks to his ear for what blocs of Jewish voters in Brooklyn want to hear. After the death of Rabbi Ovadia Yosef earlier this month, de Blasio released a tribute crediting Ovadia’s “wisdom, charity and sensitivity”—earning compliments from the Brooklyn-based ultra-Orthodox daily Hamodia, which simultaneously called out de Blasio’s Republican opponent, Joe Lhota, for his “much less respectful approach.”

Lhota, whose maternal grandmother was Jewish, has reached out to the Satmar community in Williamsburg and this week was campaigning in Fleischer’s own Bobover community. He has also attracted support among some Lubavitcher voters in Crown Heights—one of whom, Dovid Margolin, wrote a controversial op-ed last week attacking de Blasio for his support for Sandinista rebels in Nicaragua in the 1980s. (This week, Chabad’s former spokesman wrote a tart reply defending de Blasio.)

But with Lhota trailing by 40-odd percentage points in the polls, many are already looking ahead to what a de Blasio mayoralty will have to offer. Some believe he will be the best mayor ever when it comes to having a grasp of the diversity of the Orthodox landscape and the pockets of need that exist in neighborhoods like Flatbush.

“Bill, for all practical purposes, is part of the Jewish community,” says Ezra Friedlander, an influential Borough Park political operative who handled Jewish outreach for de Blasio’s rival Christine Quinn during the primary.

De Blasio’s Orthodox allies are excited about his signature plans to raise taxes on the rich to fund universal pre-K and expanded after-school programs. “We do have tremendous poverty here, and that’s not recognized in the outside world,” says Goldenberg, who met de Blasio when he was working for Clinton. “I plan on having a lot of interaction with him once he’s mayor.”

Editor’s note: This story has been revised to reflect that de Blasio supports vouchers for childcare, not private religious education.


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