Maya Wiley became the top lawyer in City Hall after writing an op-ed. It was January, 2014, and Bill de Blasio, the new Mayor of New York City, looked to many like the future of the American left. On the campaign trail, his theme was “A Tale of Two Cities”: he spoke of a New York of haves and have-nots, separated by class, race, and geography. A few days after de Blasio’s inauguration, Wiley, who was then the president of a small racial-justice nonprofit and a pundit appearing regularly on MSNBC, published a column in The Nation, arguing that New York should address racial disparities in high-speed Internet access. De Blasio had won election promising universal pre-K and an end to racist stop-and-frisk policing. Another thing a progressive mayor could do to help integrate the two New Yorks, Wiley argued, was deliver affordable Internet to poor minority neighborhoods.
Days into his term, de Blasio read Wiley’s article and called her in for a meeting; soon after, he asked her to join his administration, as counsel to the Mayor. She was an unorthodox choice. Typically, an elected official’s counsel provides legal protection the way a security detail provides physical protection. (“I keep him out of jail,” Wiley once joked.) But Wiley—whose previous jobs included stints in the U.S. Attorney’s office in Manhattan, George Soros’s Open Society Institute, and the N.A.A.C.P.—was nobody’s fixer; her background was in activism and policy. When de Blasio announced her appointment, he said that she would take on “some of the issues that are core to our agenda and need to be led from City Hall.” He cited broadband access as one of those top priorities.
During the next two years, Wiley had a hand in sending billions of dollars in city contracts to businesses owned by women and minorities. She helped shape New York’s sanctuary-city laws. In early 2016, she published another column in The Nation, touting the progress the city had made in “bridging the digital divide.” Seventy million dollars had been earmarked in the city budget for Internet access. The administration was getting tough with the big telecom firms. Several public-housing developments had been wired for broadband. “We won’t stop there,” Wiley wrote.
Six months later, Wiley was gone. That spring, amid official inquiries into de Blasio’s fund-raising, she helped craft an unsuccessful legal strategy to keep e-mails between the Mayor and outside consultants from becoming public, on the premise that the consultants were “agents of the city”—a phrase that dogs her to this day. Reportedly frustrated about being cut out of decision-making, Wiley resigned in July. (She then spent a year as chair of the Civilian Complaint Review Board, the beleaguered city agency that tries to provide independent oversight of the N.Y.P.D.) The seventy million dollars that had been set aside for Internet access went unspent, and progress on the issue stalled.
When the COVID-19 pandemic arrived, a reliable Internet connection became, for many, the only way to attend work or school, or to see a loved one’s face. Yet, at the start of 2020, more than one in three New Yorkers lacked either a mobile phone or a home Internet connection. More than one in six—one and a half million people—lacked both. Tens of thousands of children in the shelter system were thrown into a year of remote learning without access to Wi-Fi or mobile devices, or both. Internet access was an equity issue. Wiley had known it, and she’d gone to City Hall to try to do something about it. But the problem remained unsolved.
Wiley, who is now running for mayor, dislikes it when reporters ask her about the de Blasio administration. Her aides told me this several times. Wiley herself told me as soon as we met, earlier this week, in Brooklyn’s Prospect Park. I had proposed talking to her about the past eight years of city politics and how they have shaped her own mayoral ambitions. The current Mayor accomplished much of what he’d promised, including universal pre-K, the end of stop-and-frisk, and a fifteen-dollar minimum wage. And yet he had confounded many of his original supporters with his difficult public persona, his transactional methods, and his wayward Presidential ambitions. He had come into office pledging to rein in the N.Y.P.D., but, by the end of his tenure, he was defending the department even in the face of videos showing police officers assaulting Black Lives Matter marchers. New Yorkers’ mixed feelings about de Blasio will surely influence their choice of Democrat to run City Hall next year, and Wiley, it seemed, was uniquely positioned to understand this ambivalence: she’d been on the inside, had a hand in the administration’s early achievements, and left disappointed. But, before we were done shaking hands, Wiley told me that she hated my angle. “You’re asking a Black woman running for office about a white man’s record?” she said. “Come on.”
We sat down at a shaded picnic table under a tree; people passed by, walking their dogs. “Look, there’s one progressive in this race who can win this race,” she said. “And it’s me.” “Progressive,” as even Wiley concedes, is a stretchy term. Pretty much every candidate in the crowded Democratic primary has invoked it at some point in the past six months. Three of those candidates—Eric Adams, Kathryn Garcia, and Andrew Yang—are outpacing Wiley in polls. Adams and Yang also have an edge over her in fund-raising. Garcia has been riding high since receiving the Times’ endorsement, in May. All three are running on platforms that propose measures which could be called progressive—Yang’s “People’s Bank of New York,” for instance, or Adams’s call for adding hundreds of thousands of affordable apartments to the city’s housing stock. But all three have rejected arguments made by activists, reform groups, and the city’s upstart new left on issues ranging from policing to education and development. And all three have courted constituencies opposed to progressive goals.
Wiley has courted the activists. Only a fraction of the city’s voters will cast ballots in this year’s Democratic primary, and even a small edge with one reliable voting group could make a difference. Early in the race, Wiley seemed well positioned to attract the kind of coalition that had elected de Blasio: Black communities from across the city plus “very liberal” voters of all races. With only a few weeks to go, many Black voters appear more receptive to Adams, a former N.Y.P.D. captain long involved in the city’s debates over policing. Among reform-minded lefty voters, allegiances are split. Two other candidates who occupied the capital-“P” progressive space, Scott Stringer and Dianne Morales, had recently had their campaigns upended: Stringer when a former campaign volunteer accused him of making unwanted advances twenty years ago (on Friday, a second woman, who worked at a Manhattan bar Stringer once co-owned, came forward with similar accusations); Morales when several members of her campaign staff quit and others organized a work stoppage. For a lot of Morales’s and Stringer’s voters, Wiley said, “I was already their No. 2.”
Several of Wiley’s opponents have argued that the de Blasio administration was, on the whole, a failure. Yang bashes the Mayor every chance he gets, as does Garcia, the former Sanitation Department commissioner who served as a top official in de Blasio’s administration much longer than Wiley did. In October, Politico described the speech Wiley delivered at her campaign launch as a “searing rebuke of de Blasio,” but, sitting across from me, she took pains not to criticize her old boss directly. “We voted for the progressive twice, because the progressive got things done for people who desperately needed him to produce. And he did.”
When Wiley gets going, she speaks in long paragraphs, her sentences running clause to clause—a lawyer exhausting all avenues of appeal. “And I’m proud,” she said, “that I worked inside a City Hall where I was able, thanks to the Mayor being on mission and focussed, to get women- and minority-owned business contracts up from five hundred million when we walked in the door, and I got handed a title, frankly, with no staff and no resources, because the infrastructure hadn’t been built for it, in previous administrations, to actually get that up to $1.6 billion in one year.”
I asked her about Internet access—what happened there? On the campaign trail, she has often touted her work on the issue. The “Meet Maya” page on her Web site reads, “As Counsel to the Mayor, she delivered for New York City on civil and immigrant rights, women and minority owned business contracts, universal broadband access and more.” But had she really delivered on “universal broadband access”? What happened to that goal?
“Look, I left the administration five years ago,” she said. “I can’t speak for what happened in the administration over the last five years. I can talk about what I will get done.” O.K., I said, then what was her plan for getting this done if she were elected? How would she do things differently? “Let’s start by acknowledging that no city has created universal broadband,” she said. Creating it would require pulling on “multiple levers.” Ultimately, she believed that it would come down to persuading Washington to let the city use federal dollars for this purpose: “The reality is that cities can’t do it all by themselves.”
Wiley still sees a path to victory in the race, and there are reasons to not rule her out. In February, she won the backing of Local 1199 of the Service Employees International Union, the largest union in New York City and a crucial lift to de Blasio’s campaigns. Hakeem Jeffries, New York’s highest-ranking House Democrat, endorsed Wiley’s candidacy last month. George Soros, Wiley’s former employer, has spent hundreds of thousands of dollars in support of her campaign, and Local 1199 is doing the same. This week, several prominent figures of the new left—including State Senator Julia Salazar, who had previously backed Stringer—announced their endorsements of Wiley.
Wiley’s theory of the case is that many voters are just “tuning in” to the mayor’s race and that the dynamics can change dramatically in the closing weeks. Something similar had happened in 2013, when de Blasio won. Her pitch works with prospective voters, she said, when she makes it directly—they get it, even on contentious issues like policing. “I’ve talked to real-estate developers who said to me, ‘But do you support defund?’ And then, when I tell them what I’m going to do, they were like, ‘Oh, that makes sense,’ ” she said. “And then I talked to people on the left who said, we just want you to use the word ‘defund.’ And I said, I’m going to talk about what I’m going to do. Here’s what I’m gonna do. And they go, ‘O.K., that makes sense.’ Then I go into the Black community, with the folks who have the highest rates of gun violence, and they say, ‘Do you support defund or not?’ I was like, let me tell you what I’m gonna do, and then they say, ‘O.K., that makes sense.’ ” Wiley has proposed cutting a billion dollars from the N.Y.P.D. and “actually” investing in communities, while also staking out a tricky position as a defender, but not a member, of the defund-the-police movement.
More than any policy, Wiley said, what people want from the next City Hall is “courage of leadership.” But is there enough time left, even if she is right, to have this conversation, directly, with all the people she needs to have it with? “That’s why you have ads,” she said. “That’s why you have debates. That’s why you have surrogates. All that stuff matters.”
As we got up and walked away from the picnic table, Wiley conceded that she had thoughts about the de Blasio administration that she didn’t feel she could share. In other interviews, she has said that she doesn’t want to betray the Mayor’s “confidences.” Wiley, in this sense, is still acting as de Blasio’s representative, even as she seeks to be the people’s. I wished that she would say more, but our hour was up.
