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Mayor Bill de Blasio’s Crusade

Bill de Blasio is trying to remake America’s biggest city — and he doesn’t plan to stop there

Bill de BlasioBill de Blasio

Bill de Blasio leads his first Puerto Rican Day parade as Mayor of New York City.

Mark Peterson/Redux

One afternoon in early April, New York Mayor Bill de Blasio strode onto the back porch of Gracie Mansion, the Upper East Side mayoral residence, to bask in the city’s first truly warm day of spring. It had been an exacting winter, and as de Blasio folded his long frame into a wicker chair, he announced merrily, “It’s my first outdoor meeting of 2015!” When the weather suits, the mayor likes to do business out here, taking advantage of the spectacular view of the East River and the Triborough Bridge. A pair of soccer nets have been set up on the lawn, where de Blasio and his wife, Chirlane McCray, occasionally kick a ball around with their son, Dante, a high school senior.

At six feet five, de Blasio is the tallest mayor in New York’s history, and most chairs aren’t exactly built to fit his kind. Seated, he often winds up looking crouched and angular, as if he’s mentally readying himself for an especially difficult yoga pose. At political events, where he’s required to stand beside other speakers or greet constituents, he has the courteous giant’s habit of stooping slightly. His rhetorical focus can make him seem intense: His hooded eyes and hawkish features conjure a bird of prey, and his voice, despite its swallowed timbre, has a tough, prosecutorial edge. But the intensity is undercut by an ever-present air of mild distraction, and by the goofy Brooklyn-dad side of de Blasio that occasionally emerges in public settings.

Earlier that afternoon, de Blasio had convened a closed-door meeting of national progressive thought leaders and elected officials. There was Sherrod Brown, the populist senator from Ohio, and Connecticut Gov. Dannel Malloy. The novelist Toni Morrison showed up, delighting de Blasio and McCray. Other attendees included Katrina vanden Heuvel, editor of The Nation; Arizona Congressman Raúl Grijalva, chair of the House Progressive Caucus; and Van Jones, a former Obama adviser. They’d all come together to begin work on a new version of the “Contract With America,” only this one would be a product of the left, focusing on economic policies — a set of line-in-the-sand principles that progressives, and their candidates in 2016, could rally around. It was a surprising choice of inspiration for de Blasio, the mission’s unlikely Danny Ocean: Looking to rejuvenate the Democratic Party, he’d turned not to Bill Clinton, whose strategy of triangulation the mayor openly repudiates, but Newt Gingrich.

“Look, the New Democrat approach, from my point of view, didn’t work,” de Blasio told me that afternoon. “That governing approach didn’t stop the progression that led us to a thoroughly Republican House and now Senate, and a national debate that doesn’t even address the real issues. The economic crisis of today — the only parallel is the Great Depression. That’s just a fact. The difference is, there’s no light at the end of the tunnel now.” 

“He’s the furthest-left mayor by far,” says one observer. “I don’t think people realized what an ideologue he was.”

For five terms, supposedly liberal New York had been governed by a Republican (Rudolph Giuliani) and a quasi-Republican independent (Michael Bloomberg). So when a full-throated progressive like de Blasio bounded into City Hall in 2014 with an astounding 73 percent of votes in the general election, it felt like more than simply a mandate for local change. To leftist Democrats around the country, long frustrated by what they saw as the thwarted hopes, tactical errors, compromises and outright betrayals of the Obama administration, the ascension of one of their own to one of the highest-profile elected offices in the country made for a momentous, potentially thrilling development. Just as past mayors had taken advantage of New York’s unique status as a cultural and media capital to globalize their agendas — think of the far-reaching influence of Bloomberg-era public-health policies like the smoking ban, or the way Giuliani exploited his reputation for “cleaning up” the city by starting a lucrative international consulting firm specializing in security and policing — could de Blasio use the singular platform provided by his new position to showcase, as brightly as a Times Square billboard, the civic benefits of unfettered liberalism?

If judged on his ability to deliver on ambitious campaign promises, even de Blasio’s sharpest critics acknowledge he’s been successful. State Assemblyman Joe Borelli, a Republican who represents the most conservative district in New York, Staten Island’s South Shore, admits, “The mayor has been very forthright. He campaigned on a platform of ideological values — albeit, they’re not mine — but he was very honest, and he’s delivering.” Only 16 months into his term, de Blasio has expanded paid sick leave and won a hard-fought battle to secure free full-day universal pre-K (huge boons for working families), dialed back the NYPD’s stop-and-frisk policy and effectively decriminalized possession of small amounts of marijuana (both of which had a massively disproportionate effect on young men of color), launched the largest municipal-ID-card program in the country (allowing undocumented New Yorkers to more easily open bank accounts, rent apartments and access hospitals and schools), and announced a $41 billion plan to build or preserve 200,000 units of affordable housing over the next 10 years (eclipsing Bloomberg’s 12-year record of 165,000 new or preserved affordable-housing units).

Despite these considerable achievements, however, the story line of de Blasio’s Year One has been consistently undercut by establishment pushback, both organized and spontaneous, from Wall Street to the state government in Albany. Wealthy backers of charter schools broadsided de Blasio with a brutal television advertising blitz after he attempted to slow down the expansion of a hedge-fund-backed charter operation with a mixed track record but impressively high testing scores. (The mayor blinked.) Meanwhile, New York Gov. Andrew Cuomo, a centrist Democrat, seemed to relish undermining, and at times humiliating, the mayor at every turn, killing de Blasio’s proposed tax on rich New Yorkers and siding with the charter-school backers. “Historically, the relationship between mayor and governor is worse when the two are in the same party,” notes Clyde Haberman, a former New York Times metro columnist who has covered city politics since the 1960s. “It’s about who is the alpha male in town. And here, it’s Cuomo.”

And then there was the death last July of Eric Garner, an unarmed 43-year-old black man from Staten Island whose only crime was selling “loosie” cigarettes. To many observers, the video of Garner being choked to the ground by an NYPD officer looked unambiguously like state-sanctioned murder. De Blasio’s refusal to denounce the protests that followed, and the subsequent assassination of two police officers in Brooklyn by a deranged Maryland man, resulted in open warfare with noxious Patrolman’s Benevolent Association President Patrick Lynch (who said de Blasio had “blood on the hands”) and rank insubordination by a number of NYPD officers (who turned their backs on de Blasio at the funerals of the murdered officers and later staged a work slowdown, during which the number of arrests and tickets issued plummeted). 

De Blasio

The cumulative effect of this series of battles, large and small, has been to reduce the mayor in some ways, and certainly to distract from his administration’s very real accomplishments — which de Blasio himself acknowledges. “A lot of people outside New York City understand what happened in the first year of New York City better than people in New York City,” he tells me during a second Gracie Mansion interview. “But I’m convinced something very special happened here.”

It’s funny, in a perverse sort of way: That socialist-boogeyman version of Barack Obama the American right has spent the past eight years whispering darkly about? Fiction, of course. Our president has largely governed as a moderate consensus-builder. The executive-branch officeholder who comes closest to the caricature is actually Bill de Blasio. But for some reason, despite possessing a CV that could have been written by Sean Hannity’s id — traveling to Nicaragua as a 26-year-old to support the Sandinistas, being married to a radical feminist (and once-identified lesbian) by a pair of gay ministers, honeymooning in Cuba, belonging to no particular church, creating an entire department of community organizers while serving as New York’s public advocate — de Blasio has never quite joined the ranks of A-list Fox News supervillainy. On the progressive left, too, it’s been the far more charismatic Massachusetts Sen. Elizabeth Warren who has captured the imagination of the grass roots and become the object of their “anyone but Hillary” fantasies.

But in recent months, de Blasio’s team has aggressively moved to raise his profile. Case in point: A few hours before Hillary Clinton announced her 2016 presidential candidacy, de Blasio — her former campaign manager! — appeared on Meet the Press and said that he wasn’t quite ready to endorse anybody yet. De Blasio had been one year shy of 40 when he ran Clinton’s 2000 Senate campaign. Before that, his highest-profile assignment had been working for her husband’s Department of Housing and Urban Development (under Andrew Cuomo). De Blasio had also just won an election of his own — on his local Brooklyn school board. He stood out as someone “motivated by a very authentic core set of beliefs,” recalls Howard Wolfson, the 2000 Senate race’s campaign spokesman. But it’s safe to say that no one guessed he would one day be trying to make himself the head of “the Democratic wing of the Democratic Party,” to borrow a phrase from Howard Dean — let alone be stepping all over his former boss’s carefully scripted campaign launch in a very deliberate effort to push her, and the party she hopes to lead in 2016, as far to the left as possible.

“You’ve got to remember, we see Mayor de Blasio as one of us,” Van Jones tells me. “We see him as a grassroots campaigner. And when somebody comes out of our movement and becomes the mayor of the capital of the world, and then says, ‘I can’t get my job done unless the whole country comes along,’ you respond to that.” Shortly before de Blasio’s Meet the Press appearance, Chicago Mayor Rahm Emanuel, a centrist alumnus of the Clinton and Obama administrations, had endured a surprisingly feisty primary challenge from the left. “Rahm Emanuel is a historic figure, and he got drug into a runoff by somebody who I had never heard of,” Jones says. “That lets you know where that wing of the party is when it comes to the people who cast their ballot. Whatever mistakes or missteps, de Blasio is a beloved figure in this party, and Rahm is on thin ice, and that gives you a little bit of the taste of the future for this party.”

Veteran political watchers like Haberman are more skeptical. “He’s the furthest-left mayor that I can think of, by far,” he says. “I don’t think a lot of people realized what an ideologue he was. But I do wonder what he’s doing running off to Iowa and Wisconsin giving speeches. I would also point out that the last elected mayor of New York to rise to a higher office was John Thompson Hoffman, who was elected governor in 1868. Not a great record of success.”

Another prominent progressive, wishing to remain anonymous, also sounds a note of caution, despite sharing de Blasio’s stated goals. “I say this with great sympathy, but it’s going to be tough for him. The reason people love Elizabeth Warren is not because of her words — even though they are great words — but because they’ve seen her stand up to power. With de Blasio, we haven’t really seen that fight yet. Anyone can talk about inequality. Marco Rubio can talk about inequality! But everyone’s tired of just words at this point.”

In a biographical detail that sounds lifted from a fable, de Blasio was born across the street from Gracie Mansion, in a now-shuttered hospital specializing in births by older mothers. It was 1961, and both of his parents were 44: They’d met at Time magazine, where his father, Warren Wilhelm, worked as a business reporter and his mother, Maria Angela de Blasio, the daughter of immigrants from a village outside of Naples, had a job as a research assistant. The name on Mayor de Blasio’s birth certificate is, in fact, Warren Wilhelm Jr., which makes him sound like he should be foreclosing on a family-run bank in an old Jimmy Stewart movie. But de Blasio’s parents always called him Bill, and his father, who had become an alcoholic after returning from World War II, where he lost part of a leg during the Battle of Okinawa, left the family when Bill was only seven years old.

By senior year in high school, de Blasio had changed his last name, which he made official in 1983, writing in a court application, “Due to my parents’ divorce when I was eight, I was brought up essentially by my mother and her family. These individuals and their Italian heritage has been the single most important influence on my life.” Four years earlier, de Blasio’s father, dying of lung cancer, had committed suicide, shooting himself in the chest with a shotgun. “I had just turned 18,” de Blasio told WNYC, New York’s public-radio station, in the only interview in which he’s spoken about his father’s death. “I remember very vividly not going in to identify the body. I just didn’t feel up to that. My brother Steven volunteered to do it. . . . It has to be understood against the backdrop of years and years of things just getting worse and worse. On the one hand, it was a shock. On the other hand, it wasn’t a shock at all.” 

Bill De Blasio

From his mother’s family, though, de Blasio not only inherited a rich Italian heritage but also a political one. They lived in Cambridge, Massachusetts, where his parents had moved before their divorce. (The mayor of New York is a huge Red Sox fan who has bragged to The Boston Globe that he can “name you more [Sox] players than you can possibly imagine.”) Because of his parents’ age, de Blasio, unlike his peers, grew up hearing stories about the Depression and the New Deal. “It’s almost like we skipped a generation,” he says. “We would have these family gatherings, and everyone would be around the table, and it felt like there were two empty chairs for Franklin Roosevelt and [progressive New York mayor] Fiorello La Guardia. There was a reverence for them in our family. I was steeped in the notion that you take heart from a government that is trying with all its might to find a solution for you.”

According to a profile of de Blasio that ran in The Boston Globe in 1979, when he was only 17 (and already working at the Massachusetts Department of Education as a student liaison), his interest in politics started early: in sixth grade, when he found himself yelling at Nixon’s face on the family television. “My oldest brother, Steven, was a very active anti-war protester during Vietnam,” de Blasio tells me. “It was so much the water I swam in.” He did his best to draw fellow teenagers into becoming active in high school government, though the future mayor admitted to the Globe, “I get discouraged sometimes. . . . I don’t get into yelling at people, so I have a lot of pent-up feelings, but I go jogging or listen to music, soft rock or opera.”

When de Blasio moved to New York that year to attend New York University, he considered himself “sort of a junior progressive activist at that point,” he says, in particular focusing on the anti-nuclear-power movement, the meltdown at Three Mile Island having just occurred. New York had also recently come close to declaring bankruptcy, and the colorful Ed Koch was mayor. “It wasn’t quite Taxi Driver, but it was really messed up,” de Blasio recalls. “Washington Square Park was pleasantly zoo-ish, and entirely a drug market. Union Square felt absolutely unsafe. I personally never got mugged — maybe in this case height and size was a blessing — but you had to watch yourself all the time. And if you were dumb enough to leave your radio or a bag in your car, it would be stolen, or maybe the car would be stolen. We all felt it, and it was not a good way to live.”

“The New Deal was a bold action addressing people’s reality. Today, there’s nothing – it’s the anti-New Deal.”

“The de Blasio you see today really is the de Blasio I knew 35 years ago,” says Dan Katz, a labor historian who befriended de Blasio in 1980, when they were elected to represent their respective dorms in NYU’s student government. They eventually co-founded the Coalition for Student Rights, which staged demonstrations to protest issues like the rising cost of tuition. De Blasio has acknowledged being a pot smoker in his bearded, shaggy-haired student days, and Katz recalls him being a huge Bob Marley fan. “In his unguarded moments, he has an unpretentious silliness,” says Katz, who adds, “We differed politically. I was always to the left of the Democratic Party, but he had more faith that reform could happen from within.”

After attending graduate school at Columbia University, where he studied Latin American politics, de Blasio took a job as a political organizer at the Quixote Center, a social-justice organization rooted in radical Catholic liberation theology, and later engaged in protests designed to raise awareness about U.S. foreign policy. “I’m a big believer in street theater,” he says. At one action, de Blasio and other members of his group wore George H.W. Bush masks and “had this little skit in the middle of a subway car where we pretended to be having a board meeting. It was, ‘Let’s invade Central America on behalf of the wealthy and powerful! Isn’t that a great idea?’ ” When he was 26, de Blasio took a 10-day humanitarian trip to Sandinista-era Nicaragua, where he delivered food and medicine and, according to The New York Times, “took painstaking notes on encounters with farmers, doctors and revolutionary fighters,” eventually coming home with “a vision of the possibilities of an unfettered leftist government.” 

Bill de Blasio

Not long after his Nicaragua trip, de Blasio went to work for David Dinkins, the first African-American mayor of New York — and, as it would turn out, the last liberal mayor of New York until de Blasio’s own election. It was at City Hall where de Blasio met and fell in love with McCray, who was working in the press office. Give him points for persistence: McCray, a poet and activist, had been in several long-term relationships with women at that point, and early in the initially one-sided courtship, she gave him a copy of a seven-page article she’d written for Essence in 1979 titled “I Am a Lesbian” (Cover line: “BEYOND FEAR — Lesbian Speaks!”). De Blasio prevailed in this early underdog campaign, however, and the couple were married in 1994. They now have two children. (Their daughter, Chiara, is a junior at Santa Clara University in California.)

According to a story in The New York Times, staffers working on Clinton’s 2000 Senate race found de Blasio “agonizingly inefficient in a high-pressure, ever-shifting situation,” so prone to ponderous indecision and endless, inclusive-to-a-fault strategy meetings that he wound up sidelined during the final weeks of the campaign in favor of more-seasoned Clinton insiders. And yet, by the time he threw himself into the crowded field of candidates running for mayor of New York in 2013, he had spent more than a decade honing his political skills, serving two terms on the City Council and one as public advocate, and he managed to outmaneuver higher-profile opponents like Christine Quinn, the New York City Council speaker (and Mayor Bloomberg’s all-but-anointed successor). De Blasio got himself noticed by hitting Bloomberg the hardest and giving voice to the millions of struggling New Yorkers who looked at the post-9/11 gilded-age excess all around them — the stratospheric rents and impossibly high cost of living, the bank branches and chain stores squeezing out local mom-and-pops, the very skyline remade by gleaming new high-rises catering to hedge-funders and Chinese and Russian billionaires — and worried it could permanently transform the greatest city in the world into an open-air luxury mall for the global super-rich. “It was clear that the zeitgeist was turning,” says Brooklyn City Councilman Jumaane Williams. “While some people hedged, he just fully and totally embraced it.”

Longtime political consultant George Arzt, who worked as press secretary under Mayor Koch, had run de Blasio’s previous public-advocate campaign. “What I remember from that race was that Mark Green was way ahead of us — we were in single digits and Green was over 40 — and I thought, ‘Oh, boy, this is gonna be a long ride,’ ” Arzt recalls. “But Bill was so confident that this was not only doable but inevitable. He kept on saying, ‘No one knows us, so we’re going to rise and he’s going to fall.’ And it was true.”

Bloomberg lashed out at de Blasio during the campaign, and there are whispers that Bloomberg’s people are already thinking about possible challengers to de Blasio in the next election: Eva Moskowitz, perhaps, who runs the Success Academy charter schools, or Daniel Doctoroff, a deputy mayor under Bloomberg. “I hear different things from the Bloomberg camp,” one insider tells me. “I think they were taken aback at de Blasio’s inauguration, when Bloomberg was on the podium and speakers were just up there reaming him.” (New York under Bloomberg was described by one pastor as a “plantation” and by incoming Public Advocate Letitia James as “a gilded age of inequality.”) “It was unbelievably graceless,” says Haberman. “Nobody was tougher than me on Bloomberg, but, my God! You would’ve thought we were driving Adolf Hitler out of City Hall.”

Since the inauguration, Bloomberg has maintained a policy of not commenting on his successor, one which extends to his former administration officials. Wolfson, who served as a spokesman for Bloomberg   and is a current employee of the Bloomberg Foundation, will only say, “Mike Bloomberg was the best mayor in the city’s history, so anytime you hear criticism, especially if it’s not accurate, it’s frustrating.” Why, then, I wonder, was de Blasio’s line of attack on Bloomberg so successful? “I like Bill,” Wolfson says. “I have nothing but good things to say about him personally. My analysis is, it was effective to win 40 percent of the vote in a Democratic primary. That’s how I would characterize it.”

A series of oil paintings of mayors past adorns New York’s City Hall. The official painting of Bloomberg, which hangs alongside more-traditional portraits of Dinkins and Giuliani, is a telling one: The photorealist image of the mayor standing triumphantly before a sea of cubicles — Bloomberg having famously transformed the working spaces of City Hall into an open-air bullpen reminiscent of a Wall Street trading house — could have been commissioned for a cover of Fortune

Bill de Blasio

De Blasio kept the bullpen, though he’d mocked it during the campaign as leaving Bloomberg “surrounded by the voices of his inner circle . . . unable to hear the voices of the people.” Unlike Bloomberg, who worked at his own bullpen desk, de Blasio keeps a traditional office on the floor below, where he sits at the desk originally used by his hero Fiorello La Guardia. A Mets jersey is draped over a chair, and a short stack of CDs sits next to a boombox. (This reporter, seated across the room, cannot say if the stack contains Marley’s Rastaman Vibration.)

On this April morning, de Blasio has gathered the voices of his own inner circle to talk about his new housing plan, perhaps the most difficult piece of his agenda. Under Bloomberg, in particular, developers were handed the keys to the city, resulting in rapid gentrification and a mass displacement of longtime residents.

De Blasio, in blue shirtsleeves and a red tie, ate a yogurt parfait from a takeout container as he listened to Human Resources Administration Commissioner Steve Banks describe various tenants’-rights issues. (Before his appointment, Banks was an activist lawyer who had been suing the city over its homeless and welfare policies since the mid-Eighties.) De Blasio has a proactive, community-organizer’s approach to reaching his neediest constituents. His political fixer, Emma Wolfe, New York’s 35-year-old director of Intergovernmental Affairs, sits beside him; prior to City Hall, she worked at ACORN. The mayor steered the meeting and asked sharp questions throughout, pausing once to answer an incoming call on an old flip phone in his shirt pocket.

There’s a larger point, of course, to de Blasio’s economic program, beyond the primary — and laudable — goal of making New York a more equitable place for all. In a sense, the mayor is attempting to unspool a stubborn myth, the one that goes: The failures of Great Society liberalism led to the chaotic, ungovernable New York of the Seventies and Eighties, and it took stern Republican daddy figures like Giuliani and Bloomberg to make things right again. It all takes us back to a hoary, but enduring, question: Can progressives govern?

In de Blasio’s case, the answer thus far is clearly yes. It’s still too early to say much about his affordable-housing plan, but the municipal-ID program has been a huge success; more than 100,000 New Yorkers have applied since its launch in January. Ditto universal pre-K, which got online last fall, after de Blasio had been in office for only eight months, servicing 53,000 preschoolers at nearly 1,700 locations, a massive undertaking that went off seamlessly (especially compared to, say, the Affordable Care Act website launch). 

Bill de Blasio

De Blasio, for his part, takes issue with the popular narrative of New York’s resurgence. When we talk about the credit Rudy Giuliani gets for making New York safe and livable again — which de Blasio considers pure myth — I ask how much the former mayor’s outsize, room-filling personality contributed to his success. “I don’t 100 percent buy into that theory,” he says. “I agree that he was good at selling himself, and a lot of media over-accepted his version of the story. So, yeah, do you give him credit for figuring out a way to get more credit than he deserves? Sure, if that’s credit. We’ve proven not only was my model more electorally popular than his — by a lot — but that you can manage this place much more effectively if you’re not in fact creating division through the process.”

Likewise, de Blasio has problems with the notion that arose during Bloomberg’s tenure that his personal fortune allowed him to sidestep the temptations of influential donors. “Part of that was hype because he still had favorites, and a clear free-market worldview,” de Blasio says. “I mean, for God’s sake, when there was a critical op-ed in The New York Times about Goldman Sachs, he went to Goldman and gave a pep talk to the employees! When a struggling school was having troubles in East New York, he didn’t go there and give a pep talk. This theory that he traveled in no world in particular — even just the social dynamic of the people he hung around with all the time meant that it didn’t matter if they gave him money or not. They were still hugely influential to him.”

Under de Blasio, the nexus of power has certainly undergone a dramatic shift, from the Upper East Side to brownstone Brooklyn. Richard Buery, the deputy mayor who implemented universal pre-K, had been living in Westchester County when he was hired and so had to move his family into the city. When I asked where, he says, smiling, “Park Slope, of course. It’s a requirement.”

The de Blasio family didn’t move into Gracie Mansion until six months after he took office. His old friend Dan Katz recalls going to a Park Slope coffee shop last summer. “And Bill’s there, in shorts and a T-shirt. And I said, ‘I can’t believe you’re here.’ And he said, ‘Why?’ And I said, ‘Because you’re the mayor of New York.’ ”

These are superficial points of geography, of course. But also not. Park Slope represents, in its most caricatured form, a certain smug strain of contemporary New York liberalism: the land of food co-ops and yuppie toddlers wearing little Ramones T-shirts. “I’ve always found him very affable,” says Haberman. “But as mayor, there’s a sanctimony in his administration that is impossible for many people to get past.” Adds someone who has worked closely with de Blasio, “He’s very headstrong, and on a lot of answers, he’ll say, ‘Yeah, yeah, I know all that.’ ”

As de Blasio embarks on his national crusade, one has to wonder: Regardless of the validity of his message, is the mayor an imperfect messenger? As with President Obama, there’s an unattractive, imperious side to his personality that manifests in little flashes: a conversational tendency to drift toward lecture, unconcealed impatience with lines of inquiry he disapproves of. He’s also chronically tardy, a trait covered pretty much exclusively by the tabloids at first but eventually becoming pronounced enough to merit a story in the Times. (When de Blasio showed up a half-hour late for a St. Patrick’s Day parade in Far Rockaway, Queens, an area hit hard by Hurricane Sandy, the right-wing New York Post dressed him up as a leprechaun for the front page under the headline ‘St. Putz.’)

De Blasio may be a canny tactician, a scholar of progressive history, perhaps even a visionary. But populism also requires firing up a crowd, and it’s not clear if de Blasio has that touch. Or, for that matter, if he’s simply too far to the left for huge swaths of the country. The mayor “is toxic” in upstate New York, insists Rep. Borelli, the Staten Island Republican. “His message has a tough enough time resonating in outer boroughs. He got involved in several 2014 state races north of the Bronx, and they lost them nearly to a man.”

All that said, de Blasio deserves tremendous credit for the way in which he’s willing to use his bully pulpit — really, unlike few other politicians operating at his level. One morning in early March, he gave a breakfast speech to a group of business and real-estate leaders called the Association for a Better New York. The setting was the grand ballroom of the tony Pierre Hotel, overlooking Central Park, and from the back of the room, it grew quiet enough to hear the silverware clinking as the mayor, not a naturally great speaker to begin with, audaciously called on the assembled one-percenters to voluntarily raise the minimum wage in the city to $13 an hour. The applause he received was polite but restrained.

The speech was interesting for a couple of reasons — not least, because of its clear echo of a crucial moment in the campaign of candidate de Blasio. In October 2012, he gave a speech to the same group and announced his plan to raise taxes on wealthy New Yorkers to fund universal pre-K. “I happened to have a finance-committee meeting for my campaign the day before that speech, and I couldn’t tell them what I was going to do because it was just too high-security,” de Blasio recalls. “And I had people who happened to be wealthy call the next day and resign from the finance committee, and others who just stopped participating, and others who grudgingly participated but told me I had made a fatal error.”

The minimum-wage speech, in asking the local captains of industry to voluntarily join his crusade, was also a tacit acknowledgment of the difficulty of making a major impact on the economic lives of constituents, even for an executive-branch leader with as much power as the mayor of New York. At one of his first press conferences as mayor, de Blasio described his tax on the wealthy as “the number-one proposal I put forward in an election that I won with 73 percent of the vote. I think the jury is in.” But a few months later, it had been killed by Gov. Cuomo, who probably didn’t want to be seen as raising taxes during an election year, though he still provided full funding for de Blasio’s universal-pre-K plan. De Blasio was widely portrayed as the loser of that battle, though when I ask if those optics matter, he snaps, “That’s inside baseball. The people see that they got pre-K. They don’t care how it happened, and I don’t blame them. There was a lot of support for a tax on the wealthy — it was clearly a majority position in this city — and if we’re just talking about the will of the people, it would have happened. But in the end, we got the mission done.”

Still, he learned a valuable lesson about the levers of power, and he’s convinced that putting pressure on state and national political leaders is the only way to comprehensively address income inequality. He says he was “troubled by the results” of the 2014 midterms — enough to write an op-ed for the Huffington Post calling for Democrats to stop trying to run as Republican Lites. “As a progressive,” he wrote, “I know my party need not search for its soul – but rather, its backbone.” When I ask how much of the op-ed was directed at President Obama, de Blasio says carefully, “I would differentiate his words and actions. In terms of his words, I very much appreciated the last State of the Union, which was a very powerful road map for addressing these issues. But I certainly believe there should’ve been a focus on economics much earlier. I don’t belittle the crisis he walked into. And one of the few things in the last decades that has tangibly addressed the income-inequality crisis has been the Affordable Care Act. But where I would be critical is that the progressive economic vision that I adhere to was not front and center in President Obama’s vision. Though, by the way, let’s be fair — he didn’t promise it.”

There have been some cynical whispers about de Blasio’s refusal to endorse Hillary Clinton, given his historic closeness to both her and her husband, with some wondering if it’s all political theater, a bit of pro-wrestling-style manufactured heat in which de Blasio will gamely play the heel for a few months before giving Clinton his blessing, thus inoculating more troublesome pressures from the likes of Elizabeth Warren. 

Hillary Clinton and Bill de Blasio

Progressives like former New York gubernatorial candidate Zephyr Teachout appreciate the pressure de Blasio is placing on Clinton, saying his challenge is “necessary. I’d call him, and myself, traditional Democrats. It’s people like Cuomo who wandered off into trickle-down economics. We’re not to the left of the Democratic Party the way the Tea Party is to the right of the Republican Party. We’re the heart and soul of the party. It’s the private financing of campaigns that has led Democrats to these Reaganite policies.”

De Blasio’s progressive alliance will sponsor a bipartisan presidential forum later this year. When I asked if he hoped to exert a leftward pull on establishment Democrats, in the same way that a progressive primary challenger might have such an effect on Clinton, he replied, “Well, I would say it differently. Having been involved in politics, I would not say it is a given to progressives that primaries are necessarily going to result in the outcomes that you want, either a better candidate or your policies being adopted. What we’re doing here is a little more organic than that. It’s understanding that for all of the candidates, there needs to be a real push, calling on them to address these issues.”

At one point, I asked de Blasio: What had made him believe, after five terms of governance by Giuliani and Bloomberg, that New Yorkers were ready to return to progressive governance? “Well, I think I have a very different view of what happened over those five terms than many do,” he says. “I was on the ’93 David Dinkins reelection campaign, so I watched the beginning of the Giuliani era the hard way. Dinkins should’ve beaten Giuliani, but we lost touch with our own base. Dinkins lost by 50,000 votes, and there were more than 50,000 votes to be had if we had handled things differently. A lot of the people who were Dinkins voters did not feel inspired enough to vote. I’ve seen this pattern repeat over and over again. It is my critique of what happened to Democrats in 2014. So I never felt that Giuliani’s election was a renunciation of the core vision. I also feel the same about Bloomberg’s election in 2001. Yes, he had a huge amount of resources, but that was a winnable election.

“So one could argue,” de Blasio continues, “we had 20 years of Republican or Republican-independent rule that were entirely avoidable.” He says he never stopped believing New York was, at heart, a progressive city — that, on the contrary, there was pent-up demand. “It was amazing how many people thought you’ve got to be more accommodationist. And my theory of the case from the beginning was, ‘Clean lines.’ I felt, in my heart, if I had a clear message and a body of achievement to back it up, and we were organized on the ground, it was absolutely winnable. And it was.”

Turning back to his national push, de Blasio says, “In a place like New York City, with a strong local government that has a lot of tools and resources, we can do a substantial set of things for addressing inequality. But we can’t do the things the federal government can do. The federal government can make investments in infrastructure that employ a huge number of people. They could help us provide affordable housing, progressive taxation. I mean, it would be a very long list of things that the federal government could do better to address income inequality, and none of those things are happening. The New Deal was a series of bold, experimental actions to address people’s reality, and they could see and touch and feel the response in their lives. Today, there’s literally nothing. This is the anti-New Deal.

“A serious national debate would start with that. It goes beyond Hillary, it goes beyond the presidential campaign. We’re having to restart the discussion and bring it back to the reality of people’s lives.”

In This Article: Democrats, New York


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