FROM THE MAGAZINE
October 2015 Issue

Bill de Blasio’s Battle to Save New York—and Himself

Opponents, proponents, and the mayor himself weigh in on whether or not de Blasio’s vision for New York City is paying off.
This image may contain Bill de Blasio Home Decor Human Person Furniture Chair Sitting Clothing Sleeve and Apparel
Photograph by Jonas Fredwall Karlsson.

Fog hovered over Jamaica Bay that morning, November 12, as dozens of grieving families gathered for the memorial service in Rockaway Park, along the water in a far precinct of Queens. They had come to mark the 13th anniversary of the crash of American Airlines Flight 587, a flight headed to the Dominican Republic that instead ended up in flames in Far Rockaway, killing 260 people on board, as well as 5 on the ground.

Mayor Bill de Blasio was scheduled to arrive at 9:05, 11 minutes before a uniformed officer was to ring a silver bell noting the exact time of the crash. But at 9:05 there was no sign of the mayor, who was on a police launch en route. For several minutes family members stared in disbelief, some shaking their heads; the previous mayor, Michael Bloomberg, had always come early and taken his time speaking with them. When 9:16 came with still no sign of the mayor, the police officer with the bell stood motionless, unsure what to do.

Finally one of the mourners, Miriam Estrella, stepped to the podium. “I’m sorry, everyone,” she said. “Sorry our mayor’s not here.” The officer rang the bell. Nine minutes later de Blasio arrived, strode to the podium, and made a speech that did little to calm the furious families.

The mayor’s staff blamed the fog. But confronted by reporters later that day, de Blasio admitted he simply hadn’t gotten out of bed in time. “I had a very rough night, woke up sluggish, and I should have gotten myself moving quicker,” he explained. “I just woke up in the middle of the night, couldn’t get back to sleep, and felt really sluggish and off-kilter this morning.”

It wasn’t the first—or the last—time de Blasio was late for an official function. In December he showed up two hours late to a murdered police officer’s wake, arriving as it ended. During Saint Patrick’s Day festivities he achieved the trifecta of being late for three events in a row: a celebratory breakfast and reception at Gracie Mansion—“his own house,The New York Times noted in italics; a Mass at St. Patrick’s Cathedral, which Cardinal Timothy Dolan started without him (“Mayor de Blasio, we’re happy you’re here,” Dolan said when the mayor finally arrived); and a parade in the Rockaways, which the mayor missed half of. The crowd booed when he arrived. A few chanted, “Worst mayor ever.” “I’m not hired by the people to go to parades,” de Blasio said grumpily afterward.

Chronic tardiness is just one of the complaints New Yorkers have voiced about their mayor of not quite 21 months. On the Upper West Side the gripes are about potholes; on the Upper East Side, uncollected garbage; in Greenwich Village the talk is of abandoned storefronts occupied by the homeless. After 20 years of plunging crime rates, crime is again part of the New York conversation. After de Blasio criticized “stop-and-frisk”—detaining and searching people without probable cause—the N.Y.P.D. rose in open revolt against him last winter when two officers were murdered. At the funerals the policemen turned their backs on the mayor en masse.

Bill de Blasio is unlike any New York mayor in recent memory, a staunch progressive, a crusader against income inequality and for affordable housing, a man who has as little use for Park Avenue elites as they do for him. In terms of the national political scene, that makes him a far more significant figure on the left than any New York mayor in years. In fact, if you believe that the popularity of politicians such as Massachusetts senator Elizabeth Warren and Vermont senator Bernie Sanders represents a new “progressive moment’’ in American politics, it’s de Blasio who is the one who bears watching. He is the only progressive governing anything of note, and while mayor of New York has historically been a dead-end job for those seeking higher office, it’s clear his ambitions aren’t confined to the city limits.

De Blasio (then Bill Wilhelm) at New York University’s Loeb Student Center, 1980.

BY TODD MAISEL/POLARIS.

How far left is de Blasio? This is a man who cut his teeth during the 1980s raising money and distributing food for Nicaragua’s Communist Sandinista government, who later married an African-American woman who once identified as a radical lesbian, and who honeymooned in Cuba. A speaker at his inauguration memorably called New York a “plantation,” referring to inequality in the city.

This kind of talk scares a lot of New Yorkers, especially those who had warmed to the safer, sparkling city that emerged after 12 years of Mayor Michael Bloomberg, a Wall Street-trained management professional, who disdained partisan politics. Asked whom de Blasio can be compared to, one of his three deputy mayors, Alicia Glen, 48, says, “I don’t know. No doubt there is some hippie mayor somewhere who is focused on these issues. Maybe Jerry Brown when he was mayor of Oakland.”

What appears to incense many New Yorkers I spoke with is not only de Blasio’s personal style but also a sense that he, unlike Bloomberg, cares far more about politics and his pet projects than actually managing the city. “Most whites I know are left of center, and virtually every one of them can’t stand the guy—and these are all Obama-walks-on-water types,” says a journalist who has covered the city for 40 years. “This sanctimonious arrogance [he has] just irritates people. But it’s more than that. There’s no sense this man has any interest, unlike Bloomberg, in the nuts and bolts of how the city works. He’s lazy. He shows up late. He insults people by keeping them waiting, and he shrugs it off—’Oh, it’s not important I’m here on time; it matters what happens when I show up.’ But it does matter. Part of me wonders if he really wants to be mayor. I wonder if the whole idea bores him, if all he really cares about is being a national figure on progressive issues.”

“I don’t know whether he’s lazy,” says Mitchell Moss, a onetime Bloomberg adviser who now teaches urban policy and planning at NYU Wagner. “I do know he’s the first mayor in recent history to call in sick. O.K.? He doesn’t have any of that natural comfort with the details of government. People want him to reflect the tone of the city, but his agenda is one agenda and nothing else: income inequality and affordable housing. He doesn’t care about parks or potholes or anything else. He has two issues [income inequality and affordable housing] and two issues only.”

“I think people feel that it’s not a mayor’s prime responsibility to try to lower income inequality,” says Heather Mac Donald, of the conservative Manhattan Institute. “Managing New York is enough. If you can keep the streets fixed and maintain discipline in the schools, that is a challenge enough. If you can prove you have the management mettle to do that, then maybe you take on income inequality. To declare [that issue] as your primary mission as mayor strikes people as grandiose. There is a certain messianic quality that he actually thinks he can solve income inequality. I would argue that that is at the very least a premature goal, but most likely a preposterous one. To the extent that income inequality can be addressed by public policy, which is a real question, it certainly can’t be done at a local level.”

In late July, I followed the mayor through a working day and sat with him for two lengthy discussions, one off the record, over bottles of Brooklyn Lager on the porch at Gracie Mansion (the Colonial mansion that is the official residence of New York mayors), the second, on the record, at his City Hall office. When I asked him if he’s aware of the perception that he has little interest in the details of city management, de Blasio’s eyes flashed. “Sure,” he said. “And it’s wrong. But I hear it all the time.” He pursed his lips. “It wouldn’t be hard to research the truth,” he added, “and a lot of people don’t bother. I came in saying I was going to change things and acted on it, and I think there are some people who don’t like the changes, so they fill in the blanks any way they want. It’s inconvenient to their critique of me if I’m handling the budget well, or handling labor relations well, or making the trains run on time. So it doesn’t shock me.”

“I do believe [the elites] all think we’re raving Communists,” says Alicia Glen, who joined de Blasio’s team in 2013, after working at Goldman Sachs. “That’s an easy, cocktail-party throwaway line. People are lazy. People love the familiar. Most of the people in [City Hall now] are not familiar to [our critics]. In the past 12 years they’ve been hanging out at [East Hampton’s posh private golf course] the Maidstone Club with [Bloomberg’s people] and it’s been really nice and easy…. But at the end of the day … paid child care, building rental housing, creating a ferry system—these are things any smart person running a city would be doing. The fact that these people don’t go to the same golf club as Bill de Blasio? O.K., whatever. That’s all this is about.”

De Blasio’s people are quick to point out the initiatives he has introduced that are having a tangible impact on the lives of thousands of poor people and undocumented immigrant New Yorkers, whom they feel Bloomberg ignored. The mayor’s centerpiece achievement has brought free pre-kindergarten education to every New York family and free after-school programs for most—a boon for working parents. He has also introduced mandatory paid sick leave and an ambitious program for city identification cards for undocumented residents, allowing them access to city services and facilities.

Such achievements have earned de Blasio praise from unexpected quarters. “I understand why people are concerned, because some of what he says is a little scary,” says Hamilton James, president of Blackstone, the big Wall Street investment firm. “But can they object to universal pre-K? Of course not. [His deals with] the unions? He’s actually cut deals that are better than most of us thought he could get. He’s gotten an awful lot done in a short time.”

“A lot of people, white people, really want to hate this guy,” says a veteran City Hall reporter who knows the mayor well. “You know, helping all these poor people? It’s not pretty politics. No one wants to watch this get done. But it’s what he promised. And it’s what he’s doing.”

Nevertheless many New Yorkers—and not just the Manhattan elites—appear unconvinced, and de Blasio’s poll numbers reflect it. A Quinnipiac University Poll in early August found that only 33 percent of New York City voters rated life in the city “very good” or “good”—the lowest number ever measured by the university, and 47 percent believed de Blasio does not deserve re-election.

His critics would have you believe de Blasio is New York’s most reviled mayor ever. Does he deserve it?

Notes from the Underground

I first catch up with the mayor happily on schedule as he lopes through the bowels of the American Museum of Natural History on his way into the subway. On the platform, flanked by his security detail, he greets a pair of uniformed cops as the B train roars into the station. At first, no one inside the half-empty car recognizes the familiar figure in their midst. “There’s two types of rides,” de Blasio tells me, grasping a center pole. “One, when no one notices me. Two, when the whole car presses forward and everyone wants selfies. It’s a little surreal. Sometimes I miss my old life.”

Sitting to one side, a middle-aged African-American woman makes eye contact. “You’re a handsome guy!” she exclaims.

De Blasio steps over for a hug. As if on cue, a pair of city workers step up for handshakes and selfies. De Blasio smiles and accommodates. We talk about his past role models in the job. “La Guardia was a big part of it,” he says, mentioning Fiorello La Guardia, the popular mayor of New York in the 1930s and 40s. “He was the first true progressive mayor and was beloved in a way none of us will ever achieve. New York is a very emotional place, a lot of big emotions, and everyone is pressed together so tightly. And La Guardia brought this real sense of caring, of a personal give-and-take with every New Yorker. After that, people had this new vision of the mayor.”

At West Fourth Street, de Blasio strides up a flight of stairs and boards the A train, which takes him toward City Hall. This time he is noticed and consents to a dozen more selfies. “How you doing, brother?” he asks one young African-American man who hangs back. The man beams. Of the 25 or so people who approach during our ride, at least three-quarters are black, perhaps unsurprisingly, since de Blasio has a black wife and his Yale-bound son has an enormous Afro. “And then Ed Koch,” de Blasio continues, “he borrowed the template from La Guardia, a real expectation of how the mayor has to be.” I remark that, political philosophies aside, de Blasio’s style bears little resemblance to that of La Guardia (a publicity-hungry dynamo obsessed with infrastructure) or Koch (a publicity-hungry lovable obnoxious-uncle type).

A young de Blasio with his mother, Maria Wilhelm, in the late 1960s.

De Blasio, by comparison, can come off as a wallflower. There is no sense of alpha male about him. “There is a heavy-ego, solitary model of being an elected leader,” he tells me. “We’ve certainly seen that in some other mayors of this city…. I have much more of a Movement mentality. It’s much more of what I’m steeped in. I don’t think it is first and foremost about me. It’s about the ideas and the agenda…. What I think it is about me is I’m not afraid to try these new things.”

In person, the first thing you notice is de Blasio’s height; he is six feet five inches and looks taller. Like some tall people, he can seem awkward in public situations. He is not a natural orator, nor does he possess either charisma or gravitas. At the American Museum of Natural History, where he oversees a press conference, he relies on an uneasy smile, chuckles, and lame wisecracks. Asking for questions and getting no more, he says, “Going once … going twice.” His style is that of a nervous suburban dad trying to be cool in front of his teenager’s pals, an updated version of Clark Griswold from National Lampoon’s Vacation.

He is much better in small groups, holding eye contact, smiling easily, and speaking in complete sentences. “I think the most amazing thing is, when I introduce him to people, I’d say almost 90 percent of the time I get a phone call or an e-mail the next day saying, ‘Wow, I can’t believe how smart he is,’ ” says Glen. “No, it’s true. I think there’s some weird perception out there that he’s not very smart.”

De Blasio is by nature and training a coalition builder, who easily draws input from everyone in a room, even skeptics. At a meeting with African-American executives seeking greater access to city contracts, he makes sure every last attendee, all 25 of them, gets a chance to speak. It’s an approach that offsets the stridency of some of his campaign rhetoric. “I had been a little bit skeptical about his reaching out to the business community, because obviously, from the get-go, there was a bit of a schism,” says Jerry Speyer, a founding partner of the real-estate colossus Tishman Speyer, whose holdings include such New York properties as Rockefeller Center and the Chrysler Building. “But I can tell you, and I’ve known every mayor since John Lindsay, I’ve been extremely impressed. The one thing I appreciate is he really solicits candor and open discussion. He is enormously respectful. We don’t agree on a lot of things, but from the first time we spoke, I came away and felt, Gee, I can talk to this man.”

By the time the meeting with African-American executives is over he is running 45 minutes behind schedule. Referring to his chronic tardiness, de Blasio admits, “People in that meeting had valid complaints…. I could have said, ‘O.K., only five people get to speak, and we’re out of here.’ Presidential-style…. I do feel it’s my obligation to listen, sometimes to a fault…. I don’t want to have a meeting and leave the room without resolution…. I understand why it’s something I have to do better on.”

I ask de Blasio how he sleeps. “Physiologically, my perfect day would be to stay up until two and get up at nine…. I’ve had to adapt. Now I get up at six. I do think [my] body is adjusting to that. Too many days I’m up at three or four and I can’t get back to sleep.”

A different de Blasio emerges when he is tired, as at a late-afternoon meeting with staff implementing the pre-K program. In the middle of City Hall’s cavernous Blue Room, beneath the gaze of an immense portrait of founding father Alexander Hamilton, the mayor sits alone on one side of a hollowed rectangle of adjoining tables, tie removed, sleeves rolled above the elbow; the others sit across from him, servile and subordinate. He has heard this all many times; he swallows at least three yawns. He sprawls, his arms enveloping adjacent chairs, then grows fidgety, his hands roaming his face, rubbing his neck and forehead, fingers picking at some unseen blemish. He talks with his hands, with a lot of pointed index fingers. With staff he has no problem brandishing authority. “All right, what else?” he says several times.

De Blasio’s management style is a work in progress—the City of New York, after all, is the first organization of any size he has ever managed, an observation that draws scoffs from his advisers. “Name me five mayors who ran anything at all before they ran a city,” snaps Glen. “Name five that ran anything bigger than a hair salon. What did [former Obama White House chief of staff and current Chicago mayor] Rahm Emanuel run before he was mayor? What did [former academic and current Los Angeles mayor] Eric Garcetti run? That’s crazy.”

A person who deals regularly with the mayor’s office on behalf of an organization he runs compares de Blasio’s management style with those of two previous New York mayors. “[Rudy] Giuliani’s people were thugs,” he says. “Bloomberg was pretty great because even if he didn’t care about an initiative personally, if his people liked it, he let them run with it. The problem with de Blasio is that he’s a micro-manager. Everything has to go up to the top, to him. And his people, though they all seem well meaning, are often not as efficient as they might be or as qualified for their posts as you might wish.”

Says a longtime political operative who admires the mayor, “I’ve known Bill a long time, and he is really more like a liberal professor or political activist than he is actually a mayor. If you look at mayors around the country, look at Rahm in Chicago, Garcetti in L.A., they tend to be more nonpartisan than not. They tend to be problem solvers: ‘What’s the problem? What’s the solution?’ Bill comes from a very different perspective. When Bill is presented with a problem, I always imagine him musing, ‘Hmm, what’s my political philosophy on this?’ He’s not a natural manager—I mean, that’s an understatement.”

“Every mayor has a troubled transition, but eventually he learns,” says a longtime Democratic consultant who worked in the Koch and Dinkins administrations. “I wish I could see some progress toward that. I wish I could see better people around him. There is no steady hand behind the wheel in City Hall. I wish I could see more attention to governance issues. And I don’t see it. I’m not alone. It’s a common view among people I talk to.”

Another common criticism is that de Blasio is prone to shooting from the hip, which can inflame situations that with time might be handled more diplomatically. A prominent figure in the New York media world cites the flap during the 2013 mayoral campaign that de Blasio waded into over the horse-drawn carriages in Central Park. The carriages, driven by men and women in top hats, are, for visitors and natives alike, the picture-perfect New York postcard scene, capturing the romance and timelessness of the city. But to the surprise of veteran New York politicians the carriages became a major wedge issue in the race. Citing cruelty to the horses, a coalition of horse-lovers helped unseat the front-runner for the Democratic nomination, Christine Quinn, who did not support the ban. But de Blasio swiftly embraced it, vowing to make the banning of the horses happen during his first week in office if elected. And yet, on fine summer days in New York, if you head to the corner of Fifth Avenue and Central Park South, you will still see the carriages lined up, waiting to take you on a ride through the park. For, despite his vow, which, bizarrre as it might seem, is still remembered by New Yorkers, de Blasio never found the votes in the City Council to accomplish what became one of his most famous promises. It underscores his main leadership problem: that he often does not clearly think through the ramifications of an idea he espouses (horses may be euthanized, carriage drivers will be out of a job) or figure out a strategy to accomplish it. This allows him to be outmaneuvered time and time again, on such issues as banning charter schools from using city buildings or capping the number of Uber cars in the city.

“Sometimes he wades into issues that are not all that substantive, which people get agitated about,” says Blackstone’s James. “The Uber thing jumps to mind. He doesn’t have to do that. The horse-drawn carriage is another thing. A totally unnecessary controversy. I would like him to be a little more like a C.E.O., you know, let your team take care of these things, take some time, make some recommendations, and these things would just fade away.”

For all the complaints, City Hall under de Blasio has been a surprisingly tight ship. There have been few significant media leaks and little sign of the kind of turf wars and infighting that commonly infest a new administration. “He made clear from the beginning he wanted a ‘coherence’ in point of view; he wanted people who believed the things we believe,” says First Deputy Mayor Anthony Shorris, who handles much of the actual day-to-day city management. “Some people want a ‘Team of Rivals.’ That’s not our thing. It makes it much easier for everyone to get along, much easier for everyone to get their jobs done, and much easier to delegate.”

The New New Normal

While de Blasio’s agenda may have struck a chord during an election year when the world was buzzing about “the 1 percent,” it was the optics of his family that made the difference, many observers believe. The de Blasios feature a German-Italian dad, a black onetime-gay mom, and two offspring, Dante and Chiara, all happily ensconced in their brick-and-clapboard row house in Brooklyn. Black, white, Italian, L.G.B.T.—the de Blasios are like a sitcom family cast to appeal to every voting block short of Hasidic Jews. It was Dante’s famous 30-second TV testimonial to his father’s progressive policies, which ended with the surprise reveal that Dante was the white candidate’s black son, that, many people believe, won his father the election. “That ad killed us,” a competitor said afterward.

Without his family, de Blasio’s life story is messier. His real name, after all, is not Bill de Blasio. He was born Warren Wilhelm Jr. in 1961, in New York City, though his parents called him “Bill” from an early age. He grew up in Boston; he remains a die-hard Red Sox fan—anathema for New York Yankee fans. De Blasio’s father, Warren senior, was a onetime business reporter at Time magazine, who was wounded during World War II and clearly suffered post-traumatic stress of some kind. He was an alcoholic. He and his wife divorced when de Blasio was seven; 10 years later, his father committed suicide, shooting himself outside a Connecticut hotel.

De Blasio was raised in the bosom of his mother’s Italian family and ended up taking their last name as his own, though he didn’t change it legally until 2001. He left Boston to attend New York University in 1979 and never went back. After graduate school and several years supporting progressive Central American causes, he began climbing the political ladder, volunteering for David Dinkins’s mayoral campaign in 1989, working as an aide in the Dinkins administration, then running Representative Charles Rangel’s successful congressional campaign in 1994. Then came a job at the Department of Housing and Urban Development, a stint as campaign manager of Hillary Clinton’s 2000 senatorial campaign, and finally the first election of his own in 2001, when de Blasio won a seat on the New York City Council. He met his wife at City Hall, working for Dinkins.

“I met him right around the corner there. Want to see the spot?” asks Chirlane McCray, who, between a peripatetic career in New York journalism and public relations, was writing speeches for Dinkins at the time. New York’s first lady comes across as serene and cerebral; de Blasio rarely misses a chance to call her his most important adviser.

In 2009 de Blasio won election as the city’s public advocate, a kind of consumer-affairs commissioner, a position that was well suited to his crusaderism. Four years later, in January 2013, he announced for mayor, one more ho-hum Democrat in a crowded field hoping to succeed Bloomberg. For six months no one paid much attention to him. But buoyed by his single-minded focus on income inequality and affordable housing, he started to inch up in the polls during the summer of 2013. Then “the Dante commercial” lit a fire beneath his campaign that carried him to victory over Christine Quinn. It did not hurt that the Democratic field was badly fractured, or that all one needed to win the primary was to secure 40 percent of the vote, which de Blasio accomplished by securing exactly 40 percent of the vote. Though he eventually won the mayoralty with 73 percent of the vote, it was the lowest turnout since 1917. Even today, there are many who feel he is an accidental mayor.

“The founding myth of the de Blasio administration is that people heard his transcendent vision about income inequality and there was a mandate for that,” says the operative and longtime acquaintance of the mayor’s, “when in fact there was a win by default. He was elected because he was running against three Democrats and a Republican who ran a shitty campaign.... He has taken this as a mandate for running this city on what he campaigned on. Bill thinks he was elected on income inequality, and he wasn’t. I think he misunderstands the electorate.”

The tone of de Blasio’s tenure as mayor was set in its opening days, when a January storm inundated the city with nearly a foot of snow. The next morning residents of Park Avenue were flabbergasted to find many of the Upper East Side’s streets unplowed; many plows, it turned out, had been dispatched to less affluent neighborhoods, in Brooklyn and Queens. When not one but two Upper East Side grandes dames tripped on potholes and broke their ankles it became urban legend that de Blasio had declared war on Manhattan’s elite.

By far the roughest moments of de Blasio’s first year involved the police. The “Black Lives Matter” movement, which caught fire in Ferguson, Missouri, in 2014, sent crowds of protesters into New York City’s streets. De Blasio pointedly refused to condemn their accusations of routine police racism, infuriating the head of the Patrolmen’s Benevolent Association, Patrick Lynch. When a mentally troubled man shot and killed two policemen last December, Lynch memorably told reporters de Blasio had “blood on his hands.” Much of the N.Y.P.D. went on a kind of work strike and seemed to be refusing to make minor arrests or write tickets; only the hard lobbying of de Blasio’s heralded police chief, William Bratton, a veteran commissioner of the Giuliani years, managed to bring matters to an uneasy truce. While Lynch and other union officials declined comment for this article, their hatred of de Blasio—there’s no other word for it—has clearly not gone away. “He is not running the city of New York,” Lynch told one group earlier this year, according to Capital New York. “He thinks he’s running a fucking revolution.”

Worse was yet to come: also in December, near the height of tensions, de Blasio told a press conference how, as the father of a black teenager, he had several times cautioned Dante to be careful when dealing with the police. “We’ve had to literally train him,” he said, “as families have all over this city for decades, in how to take special care in any encounter he has with the police officers who are there to protect him.” Lynch responded by saying de Blasio had thrown the N.Y.P.D. “under the bus.”

At his City Hall office, I ask the mayor whether he believes young men of color still have reason to fear the police. De Blasio chooses his words carefully. “It’s not about stereotyping a whole police force or the officers within it,” he says. “It’s about a history we’ve inherited that rightfully leaves a lot of parents of color—and I am not a person of color, but I have a child who is of color—it leaves you aware of the need that they understand how to make sure they understand some of the challenges…. I simply said something out loud that hundreds of thousands of people in this city could identify with.... Why can’t we be honest about that and recognize it’s something we need to overcome? I think we’re in the process of overcoming it. I think that conversation’s going to be a lot more rare over the next 10 or 20 years from now, but we’re not quite there yet.”

Talk to many political pundits in New York and they will say, off the record and under their breath, that de Blasio favors the needs of blacks and Latinos over whites, the have-nots over the haves. And yet, despite the fact that he carried 96 percent of the black vote, relations between de Blasio and the city’s black leaders have steadily deteriorated. Part of it was de Blasio’s refusal to clean house at the N.Y.P.D.; part of it was that early on he consulted with the Reverend Al Sharpton, who is openly hostile to many of the city’s longtime black leaders, some of whom now feel de Blasio is taking them for granted. The city’s most prominent black leader is the Reverend Calvin Butts, of Harlem’s Abyssinian Baptist Church. When I talked to him in July and mentioned the mayor, he was breathing fire.

The mayor and the Reverend Al Sharpton attend Sharpton’s 60th-birthday celebration at the Four Seasons restaurant, October 1, 2014.

BY DONALD TRAILL/INVISION/A.P. IMAGES.

“De Blasio, in the words of the Stevie Wonder song, ‘you ain’t done nothing,’ ” the reverend said barely 30 seconds into our conversation. “I can’t even get in to see his commissioners. I’ve built thousands of units of affordable housing. I think I met with his office of economic development once. I’ve created the first high school in the black community in 50 years, in Harlem, and I can’t even meet the [schools] chancellor. His administration is disorganized. You hear these complaints from other people, not just me. I think he feels comfortable in whoever is advising him that the black community is in his pocket. It’s not. If he’s really with us, stick with us. I need a John Brown [the white abolitionist who advocated armed insurrection] type. I feel strange saying this, but ‘People in the black community, please, don’t be taken for a ride by this man.’ ”

The reverend was just getting warmed up. He attacked the mayor for failing to put a total end to stop-and-frisk; for hiring Bratton, an architect of “broken windows” policing of minor violations like loitering; and especially for failing to fire the officer whose choke hold led to the death of a black man, Eric Garner, in Staten Island last summer. “He’s using taxpayer money to support a murderer.” Reverend Butts and other clergy met with de Blasio last spring to air these concerns. “We put pressure on him as the clergy,” Butts told me, “and as the result of that pressure he plays to the media, then he tries the old slave-master trick of divide and conquer…. [With de Blasio] it’s all a trick. You have no power, no say. His administration is not following through [on its promises], and I think, you know, it’s because he’s not a tough administrator, a tough C.E.O.

“We’ve seen liberal racists before,” Butts concludes. “I’m not going to call him a racist just yet. I just think that his posture shows great disrespect for the black and brown communities. Great disrespect. I will not call him the r-word. But it’s terrible now. It’s condescending.”

When I mention Reverend Butts’s anger to Glen, she doesn’t appear concerned. In fact, she rolls her eyes. “I’ve known the reverend for 30 years,” she says with a sigh. “He’s never been a happy camper.”

Bad Blood

When you get down to it, managing the five boroughs is only half of any New York City mayor’s job. The other half is dealing with the state capital, in Albany, where the fate of countless city measures rests in the hands of a hostile Republican-led State Senate and, above all, in those of Democratic governor Andrew Cuomo. The open secret of de Blasio’s power is that he doesn’t have that much. He manages the city and negotiates contracts with police, firemen, and teachers, but he can work only with the tools that state legislators grant him. The sole tax he controls is the property tax, which no mayor dares raise. “You sit down there as a mayor and you believe you’re the captain of the ship,” an unnamed state official told the New York Daily News this summer, “but really everything is subject to state law. You want to change the speed limit? You want to put in red light cameras? You need to flush the toilet? You need a state law. And that’s jarring.”

That unnamed official, almost certainly the same one who characterized de Blasio to The Wall Street Journal as “bumbling and incompetent,” is believed by some to be none other than the governor himself. And, in fact, Cuomo hasn’t denied it when asked—which only begins to get at the central challenge of de Blasio’s second year in office: the Andrew Problem. Though they are both Democrats and have long taken pains to play nice in public, Cuomo has undermined the mayor at seemingly every opportunity. De Blasio’s frustration finally boiled over in June, when he stunned the New York political world by openly excoriating Cuomo to reporters as a bully bent on “revenge” for de Blasio’s daring to disagree with him. Many insiders felt the mayor was committing political suicide.

“What we have here is a situation where de Blasio was turning the other cheek constantly,” says Alan Chartock, a longtime political pundit in the state capital. “I kept saying, What the hell is going on here? De Blasio helped him a lot in his last election, you know. He saved Andrew’s ass. You would think that Andrew would say thank you. On the contrary. Every time de Blasio turns around, he’s been hit on the head by Andrew. Why is de Blasio being so compliant? Everyone says the city is a creature of the state, he has to kiss Andrew’s ass. And, of course, it turns out that the more he kissed the more Andrew went into his bully mode. I don’t think de Blasio had any choice. He had to do it, or he looked absolutely feckless.”

De Blasio won’t discuss it, but it’s not hard to get a sense of his thinking if you hang around City Hall long enough. The two men go back: Cuomo was the Department of Housing and Urban Development (HUD) secretary when de Blasio was working there. Twenty years ago de Blasio viewed Cuomo as the next great hope of the Democrats. Today he sees him as a hostage to Wall Street bankers and hedge-funders.

Tensions between the governor and the mayor were rising even before de Blasio took office. His signature initiative, a pre-kindergarten program, needed a half-billion dollars in funding, and de Blasio was intent on raising income taxes on wealthy New Yorkers to get it. But Cuomo was up for re-election and made it clear he would never raise taxes in an election year. Instead, he came up with the money from state funds. De Blasio, rather than happily accepting the governor’s largesse, continued to demand the tax hike for months afterward, until it became clear the Legislature would never pass it. De Blasio, it should be pointed out, made things far tougher on himself when he openly campaigned to unseat many of the very Republican legislators he needed to get this and other measures passed.

Matters came to a head in the spring of 2014 when de Blasio was to lead an Albany demonstration organized by the teachers’ union against the spread of charter schools—private schools that receive government funding, which liberals feel weakens the public-school system. Instead of joining him, as de Blasio had hoped, Cuomo helped organize a pro-charter demonstration the very same day. According to insiders, de Blasio angrily confronted the governor afterward. He left feeling nothing was settled.

For months de Blasio searched for a favor he could do Cuomo that would require repayment when the Legislature reconvened last January. He found his chance last summer when the governor, whose re-election was expected to be a cakewalk, encountered not only a surprisingly strong Republican opponent, Rob Astorino, but the threat of a third-party candidate from the progressive Working Families Party, or W.F.P., a group de Blasio knew well. De Blasio, in a series of late-night meetings, prevailed on W.F.P. leaders to back Cuomo in return for several promises from the governor, including that he would campaign on behalf of liberal Democrats and raise the state minimum wage.

“Bill went way out on a limb for Andrew,” says a de Blasio partisan. “It was a very personal appeal. He put a lot of his capital on the line.”

When Cuomo expressed his gratitude, de Blasio felt he finally had the governor in his camp. But then came last winter’s angry confrontations with the N.Y.P.D. De Blasio waited for a supportive statement from Cuomo. It never came. When the officers turned their backs on him, de Blasio again waited for Cuomo to say something in support. More silence. According to the de Blasio partisan, the mayor confronted Cuomo afterward. “The answer Bill got was unsatisfactory,” says this person.

But, for de Blasio, the final straw came when Cuomo refused to follow through on any of his promises to the W.F.P. “The mayor was astounded,” says one person in his camp.

Matters only got worse during the legislative session that began in January. De Blasio badly needed a complicated new tax deal to spur the building of affordable housing; Cuomo tried to block it. De Blasio also wanted an extension of mayoral control over city schools; Cuomo tried to block it. The mayor ultimately won a compromise version of both measures, but it was the Legislature’s decision in June to grant him only one year of control over the schools—Bloomberg had been given seven—that drove de Blasio over the edge. “That was the moment for Bill, that was the ultimate offense,” says one Democratic power broker.

As this article goes to press, relations between de Blasio and Cuomo remain frigid. What that means for New York City going forward, no one knows. But it’s clear de Blasio will not deviate from his agenda, of which he remains enormously proud; at one point in our discussions he even compared it to F.D.R.’s New Deal.

It may not be the New Deal, but de Blasio has racked up more substantive successes than his critics are willing to concede. Besides the pre-K program, the new contracts negotiated with almost every municipal union, and the expanded paid sick leave, he all but stopped the N.Y.P.D.’s controversial stop-and-frisk policy (a tactic Bloomberg had already begun reining in), and unveiled a $41 billion plan to preserve or build 200,000 units of affordable housing over the next decade.

“This is not partisan radical stuff,” says Alicia Glen. “The fact that this is being sort of couched in ‘We’re so lefty’ is so fascinating because 90 percent of what we’re doing is just basic good business principles. Of course you’d have paid sick leave. Of course you’d have better wages. Of course you’d be investing in infrastructure…. I don’t think it’s that we’re so radical. I think it’s that the rest of the country has gone so crazy. Building rental housing? If that makes you a crazy lefty, I don’t know what’s going on in the world…. That’s a sad statement about how far to the right and crazy the country has gotten.”

De Blasio with, from left, New York City First Lady Chirlane McCray, son Dante, and daughter Chiara, on the back porch of Gracie Mansion.

Photograph by Jonas Fredwall Karlsson.

Love him or hate him, the smart money in New York City says that de Blasio is virtually ensured a second term. “What Manhattanites in the ‘Bloomberg Bubble’ don’t understand,” says the organization head who deals regularly with the mayor’s office, “is that many people in the outer boroughs love him as much as Manhattanites hate him. But even more important is that the city’s builders love him, and they have always elected the mayor in New York City, by funneling more money than anyone else to their chosen candidate. Why do they love de Blasio? Because he doesn’t give a damn about urban planning, density, or architecture. He only cares about more affordable housing. For the builders that means they get to build an extra 20 floors and do it with fewer restrictions.”

“Being progressive in a municipal sense is investing in the people that make cities great,” Glen says. “We try to use cities to raise people up, right? That’s the history of cities. Why do people go to Rome instead of staying on their chicken farm in the middle of God knows where? Because cities are where opportunity and innovation happen.” Thus a city, she argues, is the perfect place for a crusade like de Blasio’s. “It is the petri dish,” she concludes, “where people can get shit done.”