Bill de Blasio is on the brink of becoming New York's mayor. What does he really believe?

Spencer Platt/Getty

"I am going to talk about Joseph Stiglitz every chance I get!" Bill de Blasio barks at me over his cellphone. De Blasio, New York's public advocate, has quickly surged from an also-ran to the frontrunner in New York's mayoral race—and Stiglitz is part of the reason why. The Columbia economist is one of a handful of liberal luminaries—the list includes George Soros, Nation editor Katrina vanden Heuvel, Howard Dean, and Susan Sarandon—who have endorsed de Blasio's candidacy, helping to make him, virtually overnight, the preferred candidate of New York's progressive left.

That, in turn, has vaulted him into frontrunner status with little over a week remaining until the Democratic primary: the most recent Quinnipiac poll has him winning 36 percent of the Democratic vote, up about 15 points over his chief rivals, City Council Speaker Christine Quinn and former city comptroller Bill Thompson—and close to getting the 40 percent needed to avoid a runoff. Liberals, locked out of Gracie Mansion since the David Dinkins era, are dreaming of finally getting one of their own to govern Gotham.

De Blasio has been working hard to become the election's left-wing standard-bearer for the better part of a year. He adamantly opposes stop-and-frisk; he is the only mayoral candidate thus far to be taken off the campaign trail in handcuffs (as part of a public protest against the closing of a local hospital a few weeks ago); and a centerpiece of his campaign is a plan to tax New Yorkers who make more than $500,000 in order to pay for universal prekindergarten and after-school programs for middle-schoolers—in his words, "a very small impact for a very good cause."

“As a woman,” Sarandon said of her choice to endorse de Blasio rather than Quinn, “you can’t just vote your vagina.” Mario Tama/Getty

But de Blasio's most important maneuver has been to capitalize on liberal frustration with Mayor Mike Bloomberg—and with Quinn, who set herself up as his ideological heir and was long the presumed frontrunner in the race. Quinn's campaign platform was essentially a reassuring message to centrist voters that the gains of the Bloomberg years—in a city where crime and grime have been replaced by bike lanes and beach access on the waterfront—would not be lost. Unfortunately for her, it turned out that many liberals were sick of Bloomberg and wanted someone more, well, liberal.

No one understands this dynamic better than de Blasio himself. I asked him recently if his campaign is where he thought it would be when he announced his candidacy last winter. "Broadly, broadly," he replied. "I think it comes down to the fact that I have presented a clear and consistent progressive vision, and I think there is a very substantial part of the electorate that believes in that, and I think that is going to grow."

De Blasio's strategy—relentlessly attacking a fellow Democrat for not being liberal enough—has been a familiar script over the last several election cycles in New York politics. "It is the same tactics of the left going after the left," says one local operative who isn't aligned with any candidate. "You court the liberal groups, Harry Belafonte, Katrina vanden Heuvel. Then you get the Nation endorsement. Then Katrina tweets about you. Then the Huffington Post picks up on it. A few weeks out, poll numbers start to rise."

Now de Blasio's success in using this strategy has conservatives and some city elites sounding the alarm. "De Blasio is so far out of the mainstream that even the thought of him as mayor should frighten every New Yorker," wrote the New York Post in its endorsement of Quinn. "A de Blasio mayoralty would be an express train right back to the bad old days of the 1970s." While Bloomberg himself has not endorsed any candidate, his chief spokesman, Howard Wolfson, has been sniping at de Blasio on Twitter—and recently told a television interviewer that the frontrunner "wants to take the city back to a different style of governing, where we had higher taxes, where we had more regulation on business, where we had more permissive policing."

Quinn set herself up as Bloomberg’s ideological heir and was long the presumed frontrunner in the race. Ozier Muhammad/The New York Times/Redux

In short, de Blasio and his opponents agree on one thing: that he is very, very liberal. But just because he is running as a committed lefty doesn't guarantee that he's going to charge into the mayor's office and immediately set about fulfilling progressives' dreams. In fact, while de Blasio is undoubtedly progressive, he may also be far too savvy a political operator to be the kind of mayor his staunchest supporters hope for or his detractors fear.

BORN WARREN Wilhelm Jr., and raised in Cambridge, Massachusetts, de Blasio took his mother's maiden name after moving to New York City to attend NYU. (His parents had separated when he was 7.) He met his wife, Chirlane McCray, in 1991, when both were working for Dinkins. She was an out lesbian at the time and in 1979 had written a frank article in Essence describing her experiences as an African-American, gay woman. The couple now has two children: Chiara, 18, and Dante, 15. De Blasio frequently campaigns with his family, and at a recent tour of senior centers in Caribbean neighborhoods of central Brooklyn, Dante—sporting an oversize Afro and recognizable from TV ads where he makes the case for his father—was more of a star attraction than the candidate himself. ("Come here and let me hug you," one elderly woman said to him. "You are handsome, just like my grandson is handsome." Dante obliged.)

In the Dinkins administration, de Blasio served as an aide to Bill Lynch, the mayor's political guru. He ran Bill Clinton's New York presidential campaigns in 1992 and 1996, and worked for Andrew Cuomo when he ran the Department of Housing and Urban Development.

In 2000 he ran Hillary Clinton's Senate campaign in New York. But he subsequently surprised many observers by not taking a job as a big-time D.C. political consultant and instead returning to Brooklyn to run for the City Council. In that race, he was, if anything, the establishment pick, squaring off against Steven Banks, a legendary Legal Aid attorney. The race, the Daily News declared at the time, was "causing anguish among liberals and labor unions"; indeed, the article quoted a then-obscure City Council member named Christine Quinn saying, "It's like 1968 ... Do you go with Eugene McCarthy or Robert Kennedy?"

De Blasio plans to tax New Yorkers who make more than $500,000 in order to pay for universal prekindergarten and after-school programs for middle-schoolers. Keith Bedford/Reuters

De Blasio won the race, and before the start of his second term on the council, in 2005, he ran against Quinn to be speaker. (The speaker is elected by fellow council members.) He pledged to members that, if chosen, he would work to repeal the city's term-limit law, which had been passed in a referendum.

For her part, Quinn was more circumspect about loosening term limits. She went on to win the race for speaker, but by the time the term-limit issue flared up again a few years later, things had switched. This time, at the urging of Mayor Bloomberg, who wanted to seek a third term, Quinn supported changing the law, while de Blasio opposed it. Critics alleged that de Blasio had changed his position because he was contemplating running for Brooklyn borough president and didn't want to face a popular incumbent.

When I spoke to de Blasio recently, I asked him three times how he would have handled the issue of term limits had he in fact won the speakership in 2005. But he batted the question away, describing the circumstances in 2008—when the Bloomberg administration lined up the city's editorial boards and political power brokers in support of his desire for a third term—as uniquely unfortunate. "It was clear from day one that it was going to be a rush job, it was going to be a power play, that the mayor's wealth and power was going to be very much utilized to get the result he wanted, and Quinn was, and is, his chief ally," he told me. "She gave him the backroom deal. So I think everything else is theory."

Still, I pointed out, he favored overturning the law. If he was against overturning it when the moment presented itself, how, precisely, would he have gone about it? "Every one of us in public life, going through this work, learning, experiencing, evolving, it was very clear to me, having actually experienced what happened in 2008, that it was wrong, it needed to be stopped," he replied. "I led the opposition. This is what I believed, and that is what I fought for. Period."

Former city comptroller Bill Thompson is in third place in the polls. Todd Heisler/The New Yorkt Times/Redux

To some of his detractors, the term-limit saga suggests that de Blasio is less a true believing idealist than a calculating politician. "You can track his stance on certain issues based on what is convenient for him," says Lew Fidler, a city councilman from Brooklyn whom de Blasio ousted as head of the Brooklyn delegation in 2003 and who now supports Thompson. "None of these is clearer to me than term limits. He was 100 percent in favor of doing what we did, when he was running for speaker—then he literally lined up all the support to run for Brooklyn borough president, and all of a sudden he is on his high horse, saying what we are doing is amoral, it's terrible, we can't do this. What changed? The only thing that changed was his direct political interest."

In 2004 de Blasio was a paid adviser to John Edwards's presidential campaign. And in this year's mayoral race, his rhetoric about "a tale of two cities"—a line he has used to critique growing income inequality—has echoed Edwards's rhetoric from 2004 about the "two Americas." Yet while serving on the City Council, he frequently found himself on the wrong side of progressives in his district (admittedly not hard in ultraliberal Park Slope) and was sometimes blasted for favoring developers and real-estate interests over community concerns about congestion and quality of life.

For example, he sided with a developer in opposing the designation of the Gowanus Canal as a Superfund site—even as nearby residents said that the city was ill equipped to carry out the cleanup on its own. He pushed to allow luxury housing in Brooklyn Bridge Park. And he was one of the primary backers of the controversial redevelopment of Atlantic Yards into a basketball arena for the Brooklyn Nets—a nearly decade-long fight that pitted local residents against powerful real-estate interests.

De Blasio’s most important maneuver has been to capitalize on liberal frustration with Mayor Mike Bloomberg. Andrew Burton/Getty

"He said that it was necessary to stop the tide of gentrification, but everyone knows this was the most gentrifying thing to ever happen to Brooklyn," says Lucy Koteen, a local political activist who backs current City Comptroller John Liu. "He is not wrong about the 'tale of two cities.' But look at his record. Did he help level the playing field, or is he on the side of developers who have gotten rich displacing people?"

After being elected public advocate—essentially, a citywide ombudsman—in 2009, de Blasio spent time criticizing Bloomberg for failing to fulfill a pledge to reduce New York's homeless population. He also asked corporations to pledge not to spend freely on elections in the wake of the Supreme Court's Citizens United decision.

But he wasn't a fire-breathing liberal on all matters. Back when Liu looked like a legitimate candidate for mayor and someone who could also compete for liberal votes—he has since seen his poll numbers bottom out in the wake of a fundraising scandal—de Blasio sometimes tacked the other way. In 2010 he told the Association for a Better New York, a group of city elites that has worked to influence local policy since the 1970s, that "punishing Wall Street, taxing Wall Street into oblivion, couldn't be worse for New York City, and I oppose that," and said he was against any new taxes. He courted real-estate money and even moved to Bloomberg's right rhetorically by pledging to end what he said were onerous regulations on business and development.

"It is the Ronald Reagan debate question: 'Are you better off than you were four years ago?'" he told the New York Observer in 2012. "The Bloomberg equivalent is an easier environment for business than it was 10 years ago. Is it easier for business to navigate the city government than it was 10 years ago? A lot of people in the business world will say no, it is actually harder."

While serving on the City Council, he was sometimes blasted for favoring developers and real-estate interests over community concerns. Spencer Platt/Getty

"Bill de Blasio is much closer to Machiavelli than to Marx. He is not a left-wing crusader or ideologue," says one Democratic operative who has worked closely with de Blasio and is unaffiliated in this race. "He lives for the game."

Consider what took place in 2011, when de Blasio blasted Quinn in The New York Times for delaying her support of a bill mandating that developers who receive city subsidies require businesses that rent from them to pay a living wage to all employees. It was a shrewd political move, but it didn't sit well with many of the activists pushing the bill, who felt that de Blasio had actually harmed the measure's chances by making it into an issue in the upcoming mayoral race. At the time, the group Living Wage NYC said in a statement, "2013 mayoral politics should not determine the fate of the living wage bill." Stuart Appelbaum—the head of the retail-trades union, a lead organizer of the living-wage coalition, and an avowed Quinn supporter—puts his feelings about de Blasio this way: "I view him more as a politician than as an ideologue."

"I don't think that it is inauthentic. He is a tactician," says one local operative who has worked both with and against de Blasio, but is unaligned this time. "He is very good at positioning himself. He has been a flag-waving liberal, but he hasn't been endearing himself to the left, or The Nation, and those types. But he realized the pathway to victory is to get to the left of everybody else, and he got there."

In other words, no wonder he's talking about Joseph Stiglitz every chance he gets: it's brilliant politics. Adds the operative: "I don't think you can underestimate how smart he is. If he weren't the frontrunner for mayor, he would be running the campaign of whoever the frontrunner would be."

He has certainly tied up his rivals, especially Quinn, who despite a history as a housing activist and advocate for LGBT issues, is being cast as the status quo candidate. "Christine Quinn has been the most liberal person in every room she has ever been in, and now she is totally fucking stymied and doesn't know what to do," says an operative close to Quinn. "What's her message? 'I can get stuff done'? ... She thought they could get to 40 and avoid a runoff. Bill has just been politically smarter."

There's no better example of de Blasio's savvy than his arrest—perhaps the most unmayoral move the city has seen from a mayoral candidate since Norman Mailer ran for the job with the slogan "Throw the rascals in." In addition to being great theater, the incident served as a subtle reminder to voters that, in Quinn's old district on the west side of Manhattan, a beloved hospital was recently shuttered and is slated to be turned into luxury housing.

De Blasio courted real-estate money and even moved to Bloomberg’s right rhetorically by pledging to end what he said were onerous regulations on business and development. Michael Nagle/The New York Times/Redux

DESPITE AMPLE evidence that he is a pragmatic, shrewd political operator, the caricature of de Blasio as a highly ideological purist persists—serving his purposes in the Democratic primary even as it worries many moderate and conservative voters. I asked de Blasio how he would respond to the charge that he is too radical, too much of an ideologue, to run a big and complicated city. He stressed that addressing inequality was his No. 1 priority, but added, "I understand that my opponents like to misrepresent my position, but if you listen to the vision, it is a very inclusive vision."

He pointed to his work for Dinkins, Cuomo, and especially Hillary Clinton. When I asked how that helped prepare him to run the city—since it was, after all, an effort to win a political fight, rather than to govern—de Blasio bristled, as if the answer were obvious. "Well, c'mon," he replied. "It is running a very large, complicated organization, where we had to combine pieces of the organization in New York state, pieces in Washington, D.C., coordinate with the White House in the nonstop glare of the international media, and decide how to address a whole host of issues—building a very complicated apparatus while also navigating her role as first lady. Look, of course those experiences help to build skills of leadership and strategy and understanding how to deal with a very difficult and changing media environment and public environment. It is self-evident to me what a growth experience that was."

“If he weren’t the frontrunner for mayor,” says one operative, “he would be running the campaign of whoever the frontrunner would be.” Spencer Platt/Getty

What you make of all this depends on where you stand politically. To liberals who have so enthusiastically jumped on board with de Blasio, it might come as a disappointment to know that he is a bit less of an ideologue and a bit more of a politician. But for many centrists and Bloomberg supporters, understanding the full arc of his career may actually serve to calm some of their worries.

Kathryn Wylde—the head of the business-backed Partnership for New York City, a key Bloomberg ally, and someone who has known de Blasio since his HUD days—is one of many political players who suspect that his ultra-progressive campaign is at least partly a savvy tactical maneuver, rather than a purely ideological crusade. And to her, that's good news indeed. "I don't think divisive rhetoric is good for the city, but the rhetoric is his path to victory," she says. "He couldn't be more of a centrist than Bill Thompson, and he is running against Bloomberg's record because Christine Quinn is the frontrunner, and she partnered with the mayor. He is not radical. He is a very reasonable guy who is also a very ambitious guy. He likes to win."