De Blasio’s family and professional political career were launched in the Dinkins administration, but his training in hardball politics came later, from some of its craftiest Democratic practitioners. Harold Ickes helped De Blasio land a job as New York State director of Bill Clinton’s 1992 campaign. For Clinton’s second term, De Blasio worked under HUD secretary Andrew Cuomo as regional director for New York and New Jersey. Then, in 2000, he was hired to be campaign manager when Hillary Clinton ran for the U.S. Senate. The job titles and responsibilities differed, but De Blasio’s skills were deployed in similar ways. “Bill was the person you would send to deal with people,” says a fellow operative from the Hillary Clinton campaign. “He finds common ground, and he sees the chess moves six moves ahead,” says another veteran of that campaign. “For instance, he was very good at working the Orthodox Jewish community, even though he’s neither Orthodox nor Jewish.” De Blasio became the chief emissary to Dov Hikind, a conservative, cantankerous state assemblyman from Borough Park who had the potential to deliver a large bloc of votes—or to create gigantic headaches. Hikind kept pressing for the candidate—and her husband, the president—to support the pardon of Jonathan Pollard, an American intelligence analyst jailed for spying for Israel. “Bill is very real, he’s very much willing to listen, he’s very much willing to learn,” says Matthew Hiltzik, who worked with De Blasio on the Hillary campaign and now runs a top New York public-relations firm. “And while he’s a little more liberal than I am, he is someone who’s very principled in his beliefs and also at the same time pretty practical.”
In the Hillary Clinton campaign, the questions that arose were not about his political instincts but about his performance as an executive. His title, campaign manager, was misleading—the major decisions were always in the hands of Hillary’s Washington inner circle. But lower-level matters could produce prolonged discussions. One of De Blasio’s talents as an operative—the ability to see and argue an issue and a strategy from every angle—could be a liability as a boss. Friends also wonder whether De Blasio’s desire for inclusiveness in decision-making will be a refreshingly democratic improvement on Bloomberg’s top-down management or a prescription for stagnation. “The advantage of his background as an operative, though,” says a Democratic strategist, “is that it brings Bill a lifetime of relationships.”
De Blasio is in many ways a characteristic product of the city’s political system—and a master of it, as illustrated by a story that is a minor legend in city political circles. In 2003, De Blasio wanted to become leader of the Brooklyn delegation of the City Council. First he made an alliance with Al Vann, promising to share the post. Then the pair quietly went about assembling votes for the coup to depose the incumbent, Lew Fidler. To nudge the final few into line, Fidler claims, De Blasio told three different council members that they wouldn’t be the decisive swing vote—that each would merely be a little insurance margin. The three agreed, only to be surprised when they arrived in a meeting room and counted the minimum number of plotters. But they’d given their word and didn’t defect.
In the winter of 2008, though, De Blasio was coming off what, on the surface, appeared to be a significant defeat: He’d loudly and tenaciously opposed the extension of term limits for Bloomberg (though three years earlier, running for City Council speaker, he’d been in favor of an extension for council members). The loss turned out, in the bigger picture, to have significant political benefits: It raised De Blasio’s profile and gave him a jump on harnessing the Bloomberg fatigue he anticipated would peak in 2013. But in the meantime, De Blasio needed a new job. The public advocate’s office was open; the problem there was that John Liu, a fellow councilman, was shaping up as a formidable competitor.
Liu remembers an “impassioned” phone call from De Blasio urging him to shift to a run for city comptroller. Around the same time, Liu went to a breakfast meeting at Junior’s in Brooklyn with several labor leaders. They were inclined to back De Blasio for public advocate—but said Liu, too, might enjoy their support, if he switched to the comptroller’s race. “At that point, it wasn’t a difficult decision, and it was clearly an intelligent one,” says one of the participants.
Both Liu and De Blasio won citywide jobs in November 2009, with crucial backing from the Working Families Party and its union allies, setting themselves up for a run for mayor four years later. De Blasio, though, was holding a powerful ace. During the Dinkins years, he and another young, ambitious operative, named Patrick Gaspard, became fast, inseparable friends. “BillandPatrick—it was like one word,” an associate says. De Blasio’s daughter was the flower girl at Gaspard’s wedding; Gaspard’s son played Little League baseball for a team coached by De Blasio. Gaspard eventually became the political director of SEIU 1199, the city’s health-care-workers union and one of New York’s most effective Election Day machines. After serving as political director for Obama’s victorious 2008 presidential run, Gaspard moved to Washington to work in the White House and then head the Democratic National Committee, and then earlier this year to South Africa, as U.S. ambassador—but he has kept working the phones for his friend Bill. This spring, when De Blasio was struggling in the single digits in the polls, 1199 delivered a crucial endorsement, and this fall it spent at least $2 million on De Blasio’s behalf. Mayor Bloomberg has weekended in Bermuda; Chirlane McCray says she can envision a De Blasio mayoral visit to Pretoria.