Maya Wiley – The Crisis Candidate
New York magazine|February 15–28, 2021
Maya Wiley believes a traumatized city deserves a progressive mayor—and she is certain she’d be better at it than her former boss Bill de Blasio.
By Rebecca Traister. Photographs by Philip Montgomery

Maya Wiley’s parents, both activists, raised her and her brother, Dan, to be resilient. In 1973, when Maya was 9 and her brother 10, their father, George Wiley, bought a small boat. On their first day out on the Chesapeake Bay, he insisted that his children learn how to drive it and drop the anchor in case they ever encountered an emergency.

The next day, Maya and Dan went out with him again. As their father, a big and exuberant man, traversed a narrow wooden walkway on his new boat, the rusted screws holding the walkway in place gave way and he fell backward into the water. His life preserver ripped, and Wiley remembers seeing it float away. She and her brother tried to circle the boat around him to no avail, and they watched him drown.

The siblings managed to drive the boat close enough to shore to drop anchor and swam into a white beach community, where they ran screaming from house to house and were rebuffed by the first family they tried before someone finally took them in and called the police.

Maya Wiley’s mother, Wretha, insisted that her kids talk about their father’s death, actively encouraging the adults in their lives not to treat it as a taboo topic.

“I think she was right that if we weren’t talking about it, it was going to do more damage,” Wiley told me. Wretha brought her children to her final meeting with the Coast Guard, ensuring they were given their own copy of the investigation report. “She made sure we heard it: that we would be dead if we had driven the boat next to him and he had tried to climb in, because he was too big. He would have capsized it.”

“We were just little kids,” Wiley said, “but she wanted us to hear that it wasn’t our fault.”

Wiley believes in talking about hard things. Though she hasn’t often discussed this painful story publicly, she did tell it when she launched her campaign for New York City mayor in October. The conviction that her mother instilled in her, that what we don’t address directly will only fester and worsen, seems to undergird Wiley’s campaign to lead a city in the midst of its own trauma. Just four months before the June 22 Democratic primary, the pandemic rages on; restaurants and schools open and shut, doing economic and emotional damage with every swing of their doors; 1.4 million residents face eviction; some wealthy New Yorkers are profiting from the catastrophe; many have died, many more have left.

Wiley is a civil-rights activist, lawyer, New School professor, and MSNBC pundit who served as legal counsel to Mayor Bill de Blasio from 2014 to 2016. As she prepared to enter the race, her path appeared straightforward. In any other election year, her candidacy—as a nationally recognized activist with a career focused on race, poverty, and policy reform—would have been seen as practically radical. But in post-AOC, post–George Floyd New York, with a field of more than 30 candidates, at least 14 of whom are ostensibly serious about becoming mayor, several are running alongside her or to her left, and one of them, Comptroller Scott Stringer, has already wrapped up endorsements from many of the city’s insurgent politicians.

With the left lane clogged, Wiley is presenting her identity as a progressive asset. She is a 57-year-old Black woman vying to govern a city that, over centuries, with the exception of David Dinkins, has elected white men to preside over it— and so far, she’s the only female candidate to hit the fund-raising match, unlocking $2.2 million in public funding. Some of her messaging around identity is blunt. (In January, she introduced a Black Women for Maya initiative with celebrities, including Yvette Nicole Brown and Gabrielle Union; Wiley recently told the Grio that “Black women have been delivering for this country for generations … yet we are always seen as the mules and never the precious cargo.”) But some of it is subtler, informed by her experience as a Black woman who has traversed disparate spaces—Black and white, rich and poor, activist and political— while forcing the kinds of frank, difficult exchanges she sees as crucial to fixing what has been broken and unjust in New York since long before covid.

In a series of Zoom conversations throughout the winter, Wiley spoke to me from her home in Ditmas Park, where she has lived for 20 years with her husband, Harlan Mandel, who is white and works as an investment fund manager, and their two daughters, Kai, 17, and Naja, 20. Behind her, I could see rows of book-shelves and wainscoting on the walls; it looked homey, lived in. Twice, she sat in front of a striking painting by the artist Michael Platt, which shows a young Black boy at the edge of an expanse of water. It was a gift from Wiley’s mother.

Sometimes we discussed what we were watching (she and Mandel would settle in for The Mandalorian every Friday night) and what we were eating. (“I’m the get-it done-because-we-got-to-eat cook,” she said. “He’s the I’m-going-to-preserve lemons cook.”) One-on-one, Wiley is funny and foulmouthed, vivid in her recollections, and more open than many first-time politicians, who are typically tight-lipped. From time to time during our calls, one or more of Wiley’s three cats (Romeo, Maxie, Bastet) would slink into view as their owner told me how she came to run for mayor of New York.

In the spring of 2019, while Wiley was working at the New School, a group of “heavy-hitter” business leaders asked her to share her view on the upcoming mayoral contest. Implicitly, she said, they were “trying to understand: How did we get a de Blasio?” and she spoke to them about issues like affordable housing until, eventually, one of them asked her if she was going to run. “He wasn’t saying he would support me,” she said. “He was like, ‘You should be thinking about it.’ ”

That Wiley’s mayoral origin story begins with corporate bigwigs planting the seed isn’t as weird as it sounds. She has spent her professional life weaving through spheres of privilege, studying at Ivy League schools and working at foundations, universities, and cable news networks; it’s not surprising that—especially at a moment when protest culture regularly bangs up against prep-school culture—she would appeal to those who, as one elected official described to me, “maybe more naturally interested in a Bloomberg, business-first person but who understand that some version of inclusive and more equal growth is the city’s only path forward.”

Expressive fluidity—the ability to talk to anyone about anything—is part of Wiley’s theoretical appeal: Her unusual path to politics situates her as a potentially connective figure between disparate and often noncommunicative city interests.

As a guest on Ari Melber’s MSNBC show in 2018, she gently told the spiraling former Trump aide Sam Nunberg that he should cooperate with Robert Mueller’s subpoena since refusing to do so would make him look guilty and his family would prefer him at home, not in jail, for Thanksgiving. As she was speaking to him, Wiley said, she thought she might be ending her television career. “I was thinking, I’m not doing what I’m supposed to do. I’m not being dispassionate. But I was just like, Fuck it, this guy is going down the tubes.” The exchange went viral, and Nunberg tells me he still thinks fondly of Wiley.

“What she did with Sam Nunberg was what she does every day with a variety of people,” said Rachel Noerdlinger, a partner at Mercury, a public strategy firm, who worked with Wiley in the de Blasio administration. “She’ll talk to a homeless person and the CEO of Apple with the same respect and openness.” But Noerdlinger told me she also wonders, “How do you utilize that skill to manage a city in turmoil? Is being humanist enough?”

Wiley grew up in Washington, D.C, in the gentrifying but still Black neighborhood north of Dupont Circle, and attended an underfunded public school. Her father, George, who was Black, was the son of a postal clerk; he earned his Ph.D. in organic chemistry from Cornell in 1957 and worked as an associate director of core (the Congress of Racial Equality) before co-founding the National Welfare Rights Organization. Wiley’s mother, Wretha, a white woman from Abilene, Texas, was arrested while fighting to integrate schools and later became involved in third-party politics as a supporter of Dr. Spock’s pacifist campaign for president in 1972 and as the environmentalist Barry Commoner’s vice-presidential alternate on the Ohio ballot in 1980. After George’s death, the family moved into a white upper-middle-class area (Wretha would go on to marry another civil-rights activist, D. Bruce Hanson, who was white). Maya left her public school and was enrolled in a private one. It was a wrenching series of transitions for her.

She eventually craved distance from her family’s activist legacy. “I was going to college,” she said. “But to be, like, a psychologist, wanting to help people but also just kind of not being my parents.”

Rebellions sometimes take funny forms. Wiley wound up at Dartmouth in the ’80s. In her first week on campus, a conservative student paper published an anti-affirmative-action piece titled “I Be’s a Black Student at Dartmouth,” which was written in Ebonics. Perhaps it’s no surprise, then, that by the time Wiley decided to go to law school at Columbia, she was determined to work at the NAACP Legal Defense Fund. “I thought I’d be at LDF for my career,” she said, “figuring out the 21st-century Thurgood Marshall strategy, making change at the intersection of race and poverty.”

But in 1993, Bill Clinton appointed Janet Reno to become the first female attorney general, and Mary Jo White became the first female U.S. Attorney in the Southern District of New York. White tapped Jane Booth to be the first woman to head the civil division there; Booth, who had worked with Wiley on a lawsuit against St. Luke’s–Roosevelt Hospital for eliminating maternal and NICU beds in Harlem, recruited Wiley to join her.

Wiley was wary of working in government, she said but felt it was a “meaningful opportunity” to use the weight of the office on civil-rights cases. Plus she was entranced by some of the cascading representational shifts of the Clinton era: “All these women, you know?”

It was not anything like the opportunity she had imagined. Wiley found herself the only Black attorney out of the group of 50 in the Civil Rights Division and felt that she was not being given the kinds of cases she had been promised, nor the same caliber of assignments as her white peers who had been there for a comparable period. When she’d worked there nearly a year, she told her bosses directly about her frustrations but they said that she simply wasn’t ready.

“I stormed out of the office,” Wiley said. “I was like, ‘This is madness, and I can just take my butt right back to the NAACP Legal Defense Fund.’ I am literally cursing at my desk with my door open and loud. One of my next-door neighbors, who, of course, we're all white, comes in and goes, ‘What happened?’ I just let rip because I didn’t care; I was going to quit. Then my neighbor from the other side comes around and goes, ‘What’s happening?’ And the first one goes, ‘Shut the door,’ and I start ranting louder.” Her white colleagues began to ask her to second-seat their trials. “Then all of a sudden, [the bosses] were like, ‘You’re really good.’ ”

Wiley served at the U.S. Attorney’s Office for three years; she stayed mad, but she stayed. “My whole thing was ‘Y’all are going to be sad when I quit.’ And you know what? They were sad when I quit.”

That job, she said, forced her to reckon with the trade-offs of being inside a power system versus agitating from the outside. Wiley remembered lobbying the Department of Justice to join a nonprofit organization’s civil-rights case that would determine whether the Americans With Disabilities Act could cover zoning issues. This, Wiley said, was the kind of case she had taken the job for.

The DOJ said no. As she told this story, her voice quickened. “You know what it was? They were afraid they might lose.”

The failure to have the fight is anathema to Wiley. “The whole point of activism is you try to fight like hell when you know you’re Sisyphus,” she said. “My father famously said, when a friend asked him shortly before he died, ‘George, what’s the endpoint?’ He said, ‘When nobody else is hungry.’ The friend said, ‘But there’s always going to be poverty,’ and he said, ‘Well, then you never stop fighting.’”

“That’s how I grew up,” Wiley said. “Like, hell, if we stopped fighting, we’d still fucking be slaves.”

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