The 99% Mayor

Photo: Christopher Anderson/Magnum Photos/New York Magazine

He is joking, but he’s not kidding. “When I spoke last time, they needed a much smaller room,” Bill de Blasio says to laughter. “This is the glory of American democracy!” Exactly one year earlier, De Blasio had appeared before the same group, the Association for a Better New York, an alliance of city businesses and civic organizations; the turnout then, in October 2012, was 400, and the reaction was chilly—especially when De Blasio unveiled what would become a signature element of his run for mayor, a proposal to tax the wealthy to pay for new pre­kindergarten and after-school programs. This morning—fresh off an improbable, resounding victory in the Democratic primary—De Blasio is greeted by a sold-out crowd of 800 and a standing ovation.

Still, there’s a bit of tension served with the scrambled eggs: De Blasio unflinchingly repeats his vow to boost taxes, to which he adds emphatic praise for labor unions and higher minimum wages. To lighten the mood, De Blasio improvises a running joke. He decries the decline in city and state funding to the City University of New York, and the table directly in front of the podium—full of CUNY executives—breaks into loud applause. A few paragraphs later, De Blasio says he wants to restore $150 million in funding to CUNY, producing the same thrilled, noisy result. “I love these guys!” he cracks. “Whenever I need a little pick-me-up, I’ll just say the word ‘CUNY’ and this whole table will erupt!” When he opens the floor to questions, a woman from a tech firm asks how the likely future mayor feels about her industry. “I would like to have seen the same vigorous applause as from CUNY,” he says, “so you need to think about that.” But De Blasio quickly makes it clear he’s joshing, that he loves the tech sector, too. Then, a few minutes later, a representative of the hospital industry stands up and praises De Blasio. “You know, I just want to say, I’ve lost my interest in CUNY,” De Blasio says, smiling. “I think the health-care sector is where I want to put my attention after all! They placated me better than CUNY did! CUNY, it was great while it lasted.”

More laughter, but this time there’s an uneasy undercurrent. And, at a table of real-estate executives, raised eyebrows and shaking heads. They’ve got nothing against hospitals or city colleges, mind you. They’re just wondering what, exactly, the city’s next mayor really stands for.

Bill de Blasio ran probably the most surgically focused mayoral campaign in modern New York political history, relentlessly repeating a few key phrases—“a tale of two cities” … “income inequality” … “end the stop-and-frisk era”—that played brilliantly to the hopes, angers, and guilts of the city’s liberal, Bloomberg-fatigued Democratic-primary electorate. De Blasio genuinely believes in the ideals underlying the progressive rhetoric he’s been retailing; in 1988, he traveled to Nicaragua to support the leftist revolution, and he still converses knowledgeably about liberation theology. But in his own career in elected office—first as a Brooklyn city councilman and then as public advocate—De Blasio has shown a gift for the crafty compromise.

Which is why, as De Blasio nears what is likely to be a general-election landslide victory, the central questions are about just what he believes and just who he’d be as mayor. The business leaders at the ABNY breakfast weren’t all that upset about the prospect of a tax increase on New Yorkers making more than $500,000. And most weren’t buying the notion, lately promoted in a hyperventilating TV ad by Joe Lhota, the Republican candidate, that blood will run in the streets and crime will soar if De Blasio wins. The nervousness flows from something more subtle: the prospect that De Blasio will be a mayor who responds to whoever “placates” him the most, bouncing from one interest group to the next—an unsettling contrast to Bloomberg, who, whether you agreed with him or not, was a predictable and stabilizing force in city life.

And this isn’t simply a concern of the city’s wealthy elites: What’s more surprising is that De Blasio’s friends on the left aren’t quite sure of his core political identity either. “We want him to be Elizabeth Warren and not Barack Obama or Andrew Cuomo,” a labor leader close to De Blasio says. “I think that’s who he really wants to be. But I really don’t know.” De Blasio campaigned as a crusading lefty: against corporate subsidies, in favor of expanding access to food stamps and paid sick leave and taxing the rich to help the poor. Yet his formative political training came from wily realists like Cuomo and Hillary Clinton. The risk of a Bill de Blasio mayoralty is that it sputters with politically correct incompetence. But the great promise is that he might turn out to be a complicated, highly unusual mix of ideologue and operative. The stakes are high—not just for the continued vitality of New York, but as a test of whether progressive values can deliver a more equitable city.

Dante, Chiara, Chirlane, and Bill.Photo: Christopher Anderson/Magnum Photos/New York Magazine. Makeup by Elizabeth Yoon for M.A.C Pro. Hair by Takeo Suzuki.

Enter the candidate, sweating and laughing. “Hey!” De Blasio says, bounding through the front door of his Brooklyn house and spotting me sitting at the kitchen table with his wife and son and noticing that I’m wearing a dress shirt and tie. “Chris Smith thinks he’s on East 79th Street, in a townhouse!”

Which is funny and self-deprecating, because this sure isn’t the $30 million Bloomberg manse. The De Blasio homestead in Park Slope is a humble three-story rectangle covered in faded green-painted wood paneling. Inside, the first floor is a combined living room and kitchen, all of it well worn. On one wall is a small, framed drawing of the “Sodium Avenger,” a superhero created by daughter Chiara to lovingly tease Mom for banning salt from the dinner table. On the opposite wall is a vivid yellow-and-red floor-to-­ceiling poster commemorating the mid-eighties Artists Against Apartheid movement; his wife, Chirlane McCray, did poetry readings and is listed among the performers. If I needed any further indication that the city is on the verge of a radical change in mayoral style from Bloomberg, who seems as if he were born in a pin-striped suit, there’s the 52-year-old De Blasio himself: He’s just back from his daily workout at the 9th Street Y and wearing a frayed, sweat-soaked blue T-shirt and baggy gray sweatpants.

Chirlane, 58, hasn’t given up completely on getting her kids to eat healthy, but there’s only so much a mom can do with a strong-minded teenager. Dante is gobbling a second greasy slice of takeout pizza before tackling a mountain of Brooklyn Tech math homework. He has inherited his father’s heavy-lidded eyes, his mother’s bright smile. All his own, though, is the famous Afro, which Dante tugs at nervously with his left hand. “This one guy at school keeps saying ‘Go with the ’fro!’ when he sees me,” Dante says. “It’s pretty funny. It’s funny to him. I don’t mind it much, though, as long as it’s my friends who are doing it.”

Otherwise, the celebrity inflicted by starring in a charming, campaign-changing commercial doesn’t seem to have made much difference in his sixteen-year-old life. He’s more anxious about an upcoming debate-team tournament at Bronx Science than any added pressure from being the next mayor’s son. “I get my grades for myself,” he says, “and generally do not engage in behaviors that are going to incriminate my father in any way.”

Chirlane laughs, hard, but she knows he’s being honest. “Dante’s tough on himself,” she says. “He’s got standards for himself that are probably higher than the ones we have for him.”

Topping both, though, are Chirlane and Bill’s standards for themselves as parents, an outgrowth of their own difficult childhoods. Chirlane grew up in a small, predominantly white western-Massachusetts town, where her family was the target of ugly racism. Bill’s father, Warren Wilhelm, was a Yale-educated war hero who was gravely wounded in Okinawa, losing most of one leg to a Japanese grenade. Wilhelm returned and got a graduate degree from Harvard, then went to work in the Commerce Department. Bill’s mother, Maria, the daughter of Italian immigrants, graduated from Smith College and was hired by the Office of War Information. Both became ensnared in a McCarthy-era Red Scare investigation and eventually left Washington for jobs in New York and a house in Connecticut. Warren Wilhelm Jr. was born in Manhattan in 1961—he was always known as Bill, though no one in the family seems to remember why—and has brothers who are thirteen and sixteen years older. In the mid-sixties, the family moved to Cambridge, Massachusetts. Warren Wilhelm was increasingly trying to drown his physical and emotional pain in whiskey; when Bill was 7, Warren left the family. “Bill’s experience in those years was pretty bleak,” says Steve Wilhelm, one of his brothers. “Dad just kind of vanished, basically.”

Steve was living on a commune when he got a phone call that his father had been found dead of a self-inflicted gunshot wound to the chest. “He’d had lung cancer, and it was coming back, metastasizing. He wrote a beautiful letter: ‘I don’t want to die in a hospital with tubes stuck in me,’ ” Steve says. “Bill and I emerged out of all that with some clear ideas of what we would do and not want to do if we were ever parents.”

De Blasio understands all the recent fascination with his father’s story but says the attention is misplaced, at least when it comes to understanding what shaped him. “My mother was the greatest influence on my life by far,” he says. “She was often very, very sad about things that had happened to her, but she had a fierce resilience—a very sharp, purposeful resilience. She was very practical. She always talked to me about a kind of Italian understanding of the world—she would juxtapose somewhat my father’s upbringing and what she saw as sort of an American affectation for a certain romanticism, a certain idealism, with her own Southern Italian sense of practicality. She was nobody’s fool, and when the whole McCarthy thing happened, it bothered her intellectually and it troubled her personally, but she was not surprised one bit. She came out of that experience further armored. My father came out of that experience further troubled.” When Bill changed his last name from Wilhelm to De Blasio, his brothers weren’t surprised. “The Wilhelm side didn’t mean that much to him,” Steve Wilhelm says, “and like everyone, he was looking for a family.”

Photo: Christopher Anderson/Magnum Photos/New York Magazine

He extended one through politics. In high school, De Blasio was a student-­government geek; in college, at NYU, he became a leading activist, helping form the Coalition for Student Rights, which rallied to protest tuition hikes and organized an overnight sit-in of Bobst Library to demand that it stay open later. He also argued for the superiority of Talking Heads over Blondie with an NYU roommate, Tom Kirdahy. “Bill was very smart but very funny,” says Kirdahy, who remains a friend. “And he had a crush a week.” De Blasio’s interest in politics, and the underclass, deepened as a grad student in Columbia’s School of International and Public Affairs, where he shared one class, in Latin American politics, with Dan Cantor, who years later would team with De Blasio and others to launch the Working Families Party. He soon made two other pivotal friends and mentors: Bill Lynch, the wily Harlem political consultant who masterminded the winning 1989 mayoral campaign of David Dinkins, and Harold Ickes, the combative second-generation Democratic insider. De Blasio volunteered for the Dinkins campaign, then was hired as a coordinator of volunteers; in City Hall, Lynch hired him as a junior aide in community affairs. De Blasio says he learned how not to run an administration during the four tumultuous Dinkins years—“The organizational structure was divided, and there was a real lack of unity, a real lack of singleness of purpose a lot of the time”—but the most significant personal event during that period was meeting Chirlane, a press-office staffer in the Commission on Humans Rights.

De Blasio was persistent; McCray was reluctant. After a few months, she handed him a story she’d written for Essence about being lesbian. De Blasio wasn’t dissuaded. They were married in 1994, in Prospect Park, by a pair of gay ministers; McCray was three months pregnant with Chiara. “The fact that my parents’ marriage turned out so badly was not a great recommender of how easy it was to get it right,” De Blasio says. He tried psychotherapy in his mid-twenties, attempting to sort out his feelings about family. “I took a long time to believe,” he says. “And it’s absolutely connected to meeting Chirlane. That’s what finally made me comfortable, was finding a soul mate, finding someone I could believe that I could actually work it out with. And I was right.”

As his own life has become more public, De Blasio has propelled his family into the spotlight with him. Having cheery, mixed-race kids has paid political dividends, but De Blasio claims his motivation is educational as much as anything else. “You have to understand our family is different in the way we think about things. Chirlane and I met in City Hall; we had both had a history of activism,” he says. “We talked about it in broad ways; it was unspoken that we were going to pursue not only our love, our relationship, but our commitment to the world, and that was going to be a given in our lives … These are kids who, by the time Chiara was 5 and Dante was 2, they had slept overnight in the Clinton White House. [The kids] both got so much out of this experience this year, they got some real-life lessons about how the world works, but they also gained a lot of strength, a lot of confidence, a lot of understanding.”

De Blasio believes that his family would have become media fodder whether they were a prominent part of his campaign or not. And it’s true that everything about this family, as normal as it is in many ways, is inescapably political. Even the house. In 2000, when De Blasio decided he wanted to run for City Council, they moved one block so he’d be a resident of a district with an open seat. Chirlane still loves the neighborhood, but she disdains what she thinks the Bloomberg era has done to it. “The nursery school Chiara and Dante went to, both of them had fairly diverse classes—economically, racially. That was the cool thing. The two mommies, and Asian, and black, and Latino kids,” she says. “That’s not the case now. It’s gone the way of the mom-and-pop stores. It’s wealthier and whiter.”

Now the family may be relocating to the Upper East Side. McCray’s memory of one visit to Gracie Mansion is still vivid. She remembers going to a reception there in 2006 for council members and spouses. Chiara de Blasio—now 18 and a sophomore at a college in Northern California—had just begun middle school, and Bloomberg’s Department of Education had instituted a ban on student cell phones. McCray approached the mayor. “I said, ‘Mayor Bloomberg, you are my hero! Because you instituted the smoking ban, which is so important and has done so much for people who have respiratory problems in this city and for our children. I want to thank you for that. But the cell phones in the schools’—and as soon as I said the words cell phones, he turned his back and walked away from me,” she tells me. “I was so shocked. I had never had that experience before—someone just turning and walking away like that! Bill shook his head and said, ‘That’s just how he is.’ ”

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.

It’s a diner, not a metaphor. De Blasio has chosen this place because it’s two blocks from his Park Slope house, he’s hungry, and the waitress knows him so well she assumes De Blasio wants his regular oatmeal. The name of the diner does indeed seem apt, however, for a conversation about politics and principles: Little Purity.

De Blasio squeezes his six-foot-five-inch frame into a booth in the back, turning sideways to angle his legs across the seat; behind his head is a mirror decorated for Halloween with stickers of goblins and pumpkins and BOO! in black and orange letters. It’s the morning of De Blasio’s first debate with Joe Lhota, the Republican nominee, and he’s fortifying himself with an egg-white Greek omelette and some nimble sparring. In 1990, he called himself a “democratic socialist.” At ABNY, he tried on “fiscal conservative.” Does he think, in an ideal world, socialism would be a better economic system than capitalism? “I have described my philosophy,” he says, a bit testily. “My worldview is one part Franklin Roosevelt—the New Deal—one part European social democracy, and one part liberation theology. That’s how I see the world.”

He is not now, nor has he ever been, a Marxist. But De Blasio is a sincere and loyal product of the late-twentieth-century American left wing who is only half-­jokingly called “comrade” by friends. “If you look at the whole body of my work, it’s not hard at all to figure out who I am and what I believe in,” he tells me. “My grounding in progressive movements is pretty solid, and it continues to be a way I think about the world, and so I don’t think there’s any question about where I come from ideologically and how consistent my views are today.”

The question is how those ideals will translate into actual governing. De Blasio says that if elected mayor, he will push to expand the “targeting” of city contracts and jobs to minority- and women-owned businesses—not quotas—and to use zoning to increase the supply of subsidized housing. “I think we have some real methods for doing that that have been underutilized by the current administration,” he says. “Local ­hiring—recognizing that there are legal challenges but also recognizing that a number of developers have agreed voluntarily, as part of a broader negotiation process, to some kind of requirement. That is a model I think we can do a lot more with—using the power of the city government to maximize the amount of affordable housing and to maximize the amount of job creation, but also to make sure that the jobs created reach people from the five boroughs and in particular people who have been less economically advantaged.”

As a council member, De Blasio did follow through on his principles even when there was minimal political gain: In the wake of the murders of Nixzmary Brown and Marchella Pierce, he staged hearings but also spent months collaborating on ground-level improvements to the city’s child-welfare system. Bertha Lewis, the fiery housing advocate and a close friend of De Blasio’s, lauds him for holding bad landlords accountable. But De Blasio can also be elastic and opportunistic. He’s talked about the outer boroughs’ deserving the same quality of services as Manhattan, but this summer he landed large donations from the entrenched taxi-medallion owners—and sided with them against an outer-borough taxi-expansion plan. He’s been exceedingly patient on the delayed construction of subsidized housing at Atlantic Yards, a project that got key backing from his friend Lewis and whose developer, Bruce Ratner, co-hosted a birthday-party fund-raiser for De Blasio.

“On things that are not moral issues, you see what a tactician Bill is,” a former City Council colleague says. “Like horse carriages.” De Blasio declared he’d banish the Central Park ponies as one of his first mayoral acts; coincidentally, an animal-rights group bashed Christine Quinn for months, with some of its money coming from a major De Blasio donor. After winning the primary and being endorsed by the union that represents hansom-cab drivers, De Blasio has been a bit wobbly, first saying he’d “start the process” to institute a ban, then insisting the move is still a high priority. He trumpets transparency but last week shut the press out of a $1 million fund-raiser starring Hillary. None of those moves were corrupt, or even hypocritical, necessarily. But they were the footwork of a political pro. “I think he’ll be able to manage the conflicting pressures and stay true to his values,” says Bob Master, political director of the communications-workers union and a co-chair of the Working Families Party. “But look, do I think this is a guy who will never compromise? No. And we don’t want somebody like that. We want somebody who understands how to push things as far as you can go and make the best possible deal when it’s available.”

De Blasio’s signature campaign promise will test his political skills immediately once he’s elected—actually, the machinations are well under way. De Blasio needs state legislative approval to raise taxes on wealthy city residents and fund the pre-K and after-school programs that he says will slowly close the economic divide. Governor Cuomo, who says he’s determined to lower New York’s taxes, has questioned whether the proposal is merely campaign rhetoric. “Never forget that Bill worked for Andrew” at HUD, a Democratic strategist says. “And Andrew will always see the relationship that way.” The dynamic won’t be nearly that simple, though. De Blasio’s camp believes a landslide in November will become momentum in Albany. “Andrew is going to want De Blasio to help him next year, big time, on the left,” a pol who knows them both says. “Now, here’s the dilemma for De Blasio: What does he do if Andrew gives him the money for pre-K but eviscerates poor people outside the city?”

De Blasio often begins his answer to tough questions with a version of “Let me frame this,” and then proceeds to rearrange the subject to his advantage. It’s a skill he shares with Cuomo—and one reason he thinks he understands the governor’s psyche so well. “Bill is New York’s leading Cuomo-ologist,” a liberal strategist says. “Whenever we had questions about Andrew, it was, ‘Call De Blasio!’ ” He is being careful not to antagonize the governor even before he’s officially mayor. The pending state referendum on the expansion of casino gambling provides an intriguing example. You might expect De Blasio, the “true progressive,” to oppose such a regressive industry. But in addition to seeing policy benefits from casinos, De Blasio the pol knows that the referendum is highly important to Cuomo. “I don’t accept the characterization [that legalized gambling is incompatible with progressive values], first of all,” he says. “That may get back to my mother’s pragmatism. The industry exists. It’s state sanctioned when you call it Lotto. The money and the jobs are going elsewhere; we’re not in a position to let that kind of economic impact go elsewhere. And you know, since that is the reality, certainly the financial impact on a city, if we get $50 million, $100 million, whatever the final figure is each year for our schools, you know, that’s gonna do some good. I think it’s a very practical equation. I think we have to, at the same time, try to address the underlying dynamics—help people get the best jobs, the best education possible, then they will make their own choices.”

The financial industry won’t be going away, either, despite its fears of De Blasio. One fringe benefit to his enormous general-­election lead over Joe Lhota is that De Blasio has had time to sit down with Wall Street giants and real-estate-industry players, cashing their checks and parrying their skepticism. “I don’t think we have to have a philosophical ‘Kumbaya’ moment,” De Blasio tells me. “I think it’s clear I’m a progressive and that if the people choose me, I’m going to take this city in a progressive direction to address these inequality issues, and I think that certainly some of the business leaders I have met are not particularly interested in doing that. Some are, to be fair—there are some very progressive people within the business community who have told me with energy that they agree the inequality crisis is getting out of hand. All I care about there is where we have to work together practically to create jobs.” A top Democratic strategist who has worked with De Blasio puts it much plainer: “He’s more pragmatic than progressive. He’s a deal guy—which is why Wall Street should love him. They’re deal people, too!”

De Blasio is far from selecting a City Hall lineup, at least publicly. His campaign aides quickly bat down the names of potential commissioners that have been floated in the media, leery of looking overconfident, even with a 44-point lead. “I’ve been talking to people for advice for the last year or two while simultaneously assessing them,” De Blasio tells me. “You can do a lot of deep thinking, a lot of playing things out in your mind. If I’m the one [elected], I’m certainly not going to be caught flat-footed.”

The exception to this wariness, however, has been instructive. De Blasio himself has talked up two people he’d consider selecting for police commissioner. The first, Bill Bratton, is associated with dramatic turnarounds in both Los Angeles and New York—and, usefully for De Blasio, Bratton is also remembered positively by many in the city for clashing with Rudy Giuliani. The second, Philip Banks III, is currently chief of department in the NYPD—and, usefully for De Blasio, Banks is ­African-American. Both are law-enforcement lifers and very much in the mainstream of policing theory and practice, which allows De Blasio to tamp down worries that he’d make radical changes in a department that’s reduced crime to record lows. But, again, the floating of these names is more political than executive. De Blasio is savvy enough to understand the downsides: Bratton is a media magnet, and some police insiders consider Banks too nice a guy to run the department forcefully.

De Blasio’s ultimate choice for NYPD commissioner will be judged against the clarity of his campaign rhetoric. Given his belief that stop-and-frisk tactics have antagonized innocent residents of minority neighborhoods, wouldn’t hiring a nonwhite police chief to succeed Ray Kelly be a step toward healing what De Blasio claims is a dangerous rift? “I think the philosophy is the most important thing and the capacity to implement that philosophy,” he says. “So, I want a community-policing worldview, I obviously want to bring policing and the community back together, I want to fundamentally reform our current approach, and whoever can do that most effectively, that’s my priority. It’s less about demographics.” The other high-profile pick a Mayor De Blasio will need to make is for schools chancellor. As a candidate, he’s talked about greatly increasing parental participation in the school system and about reducing the Bloomberg-era breaks given to charter schools. Beyond that, however, De Blasio has been vague about what he considers the best ways to improve the city’s public schools.

In shaping his administration, De Blasio says he intends to borrow a goal from one of his former bosses, Bill Clinton, and strive to assemble a Cabinet that looks like New York. And New York, increasingly, looks like De Blasio’s family, which is one reason he’s stirred such optimism. His household touches more than a hopeful multiracial chord—it also represents the economically beleaguered middle class, a segment of the city that hasn’t been at the center of the Bloombergian universe. De Blasio is a true believer in the importance of unions in bolstering the middle class; he has been close to the movement much of his life—a cousin, John Wilhelm, rose to become president of the hospitality-and-textile-workers union. So De Blasio would enter office with an enormous reservoir of goodwill. He’ll need every ounce of it: The next mayor will be trying to find the money to pay thousands of civil-service workers whose contracts expired as many as six years ago—and who could ask for as much as $7 billion in retroactive raises. Real leaders, though, tell allies things they don’t want to hear; isn’t De Blasio going to need to disappoint some of his union boosters? “You misunderstand the theory I’m putting forward,” he says stiffly. “I’m not here to tell them how much they’re gonna hate me. I’m here to tell them that we are going to get to a deal and balance our budget. The whole campaign and all that preceded it was telling people things they didn’t want to hear. Telling the wealthy they were going to pay more taxes, telling developers they were gonna be required to create affordable housing. Go down the list, and the last time I checked, those are some powerful positions you could have.”

True, but too easy: The wealthy and the real-estate interests aren’t the people who have put you in a position to win the mayoralty. “But, hold on,” he says. “It’s native to me that when you have a sense of mission, you keep pursuing the mission, and you give people an opportunity. Put people around the table and say, ‘Here is our task, here is the budget we have to balance, here’s the money we have, here are the options of how to do it. I need to find cost savings.’ That is usually a phrase that a lot of labor doesn’t like to hear at the jump. But I’m not here to say, ‘Look how big and bad I am,’ because that approach with Bloomberg and many others simply failed. I am here to say, ‘Let’s work together for a common good.’ ” And here’s where De Blasio’s gift for seeing multiple angles helps: Achieving the tax increase on the wealthy could make it easier for him to get labor unions to swallow reductions in benefits.

De Blasio will be a significant shift in tone and style from Bloomberg. The hard part will be how much, and how quickly, he can deliver on the substance of rebalancing city life. Hasn’t his campaign raised expectations unrealistically? “I’ve obviously thought about this issue,” he says. “The combined impact of all the pieces we’re talking about—the early-childhood and after-school plan, the affordable-housing plan, paid sick days, living wage, reprogramming dollars to small business and to CUNY—a lot of pieces packing a lot of firepower. And they’re going to add up to a lot.” Here he nimbly injects a note of caution. “So, is it going to end the problem of income inequality? Of course not. But do I think it will make a noticeable contribution toward progress? Do I think people will feel movement on a lot of different fronts and a real commitment from City Hall to addressing these issues? Yeah.”

One week before I visited him at home, De Blasio had been in the plush corporate boardroom at Viacom, lunching with the likes of Philippe Dauman, the media conglomerate’s chairman, and Rupert Murdoch, whose Post had been running a red-and-black caricature of “Che de Blasio.” Before the talk turned to sticky subjects like taxes and charter schools, De Blasio turned to Lloyd Blankfein, of Goldman Sachs—but also, De Blasio pointed out, a man who’d grown up in a Brooklyn public-­housing project and knew what it was like to be among the striving have-nots. It was a smart attempt at connecting; Blankfein, afterward, said De Blasio had made a favorable first impression.

Now De Blasio stomps down the stairs into his endearingly cramped living room, freshly showered and gray-suited and ­yellow-necktied, ready to head to midtown for another fund-raiser, this one crowded with real-estate executives. Does Chirlane worry that all this wooing of the one percent will change her prole-loving husband? “Bill? No,” she says firmly. “Not in a bad way. People change, because they have to grow in order to live.” Bill de Blasio leans down, kisses his wife, and heads out his rickety front gate and into a mammoth black SUV, slipping into the front seat, next to his NYPD driver, and getting comfortable with his ride to power.

The 99% Mayor