Can Maya Wiley Break New York City’s Glass Ceiling?

In the early 1970s, when Maya Wiley was in first grade, attending a de facto segregated, underfunded public school in Washington, D.C., a boy named Carlos — Wiley described him as her “little boyfriend” — showed up at her door every morning and walked to school with her. But one day, he didn’t show up; it was like he’d “disappeared,” remembered Wiley. A year or so later, her best friend Charlene — “we ran the streets together” — disappeared from Wiley’s life, too. 

Wiley asked her mother where all her friends were going. Why couldn’t they play together anymore? Wretha Wittle Wiley, a civil rights activist, explained to her daughter that Charlene’s family had moved after the landlord had increased their rent, and that a similar thing had happened with Carlos’ family. Although Wiley was too young to fully understand that there was a name for why her friends and neighbors were disappearing from their neighborhood of Adams Morgan — gentrification — she was old enough for the experience to make a lasting impression on her, one that still informs how she views local government’s responsibility toward preserving the homes and livelihoods of its most vulnerable citizens, even as it works to expand public projects. One reason gentrification was accelerated when Wiley was a child in Adams Morgan was the construction of a nearby Metro stop, which made the formerly working class neighborhood more desirable and accessible to people with more money. It’s not that having more access to public transit was a bad thing in itself, says Wiley now, but it’s that no one in city government thought about how to protect the homes of the people who already lived there. Eventually, their landlord increased Wiley’s family’s rent, and they also had to move out.

Realizing from a young age that her city wasn’t invested — or investing — in her livelihood deeply shaped Wiley’s career and her sense of how local government should work. It was also a big influence in why Wiley is now among the top contenders running to replace Bill de Blasio as Mayor of New York City.

“I think for all of us, our early experiences absolutely shape our understanding of the world and what we want to do in it,” Wiley tells Refinery29. “It was a traumatic experience to just have a friend disappear. You don't even get to say goodbye. You don't know where they end up. Even as a little kid, you know it's wrong, that there's something unfair about working hard and not being able to afford the rent. … So, my experience was literally losing a whole neighborhood, and one that shaped me.”

“It was a very personal and emotional experience,” she adds. “But as a civil rights lawyer and as a racial justice advocate, I also [came to understand] how all of these were decisions being made by people in government. And it hurt us — it hurt us.”

Perhaps another reason why seeing all her friends disappear was so formative for Wiley, was that it was also at this point in her life that Wiley lost her father, George Wiley, a civil rights activist, who died in a boating accident for which 9-year-old Maya and her brother, Dan, were present. Wiley’s mother encouraged her children to talk about and process their feelings, rather than staying silent and treating it as taboo, she has said, explaining how important that was for her ability to heal. It was also an approach that seems to have helped lead Wiley toward a life of public service and speaking on issues that affect vulnerable people. After receiving a law degree from Columbia University, Wiley worked at the NAACP Legal Defense and Education Fund, at the ACLU, and as an assistant U.S. attorney for the Southern District of New York. She was also a co-founder and the president of the Center for Social Inclusion, a group devoted to ending structural racism. From 2014 to 2017, she served as counsel to de Blasio, before chairing the NYC Civilian Complaint Review Board (CCRB), where she recommended the city bring charges against Daniel Pantaleo, the police officer who killed Eric Garner, a move that was critical to Pantaleo’s eventual firing. Over the last few years, she has appeared as a political and legal analyst on MSNBC, where she convinced ex-Trump aide Sam Nunberg to comply with Robert Mueller’s subpoena, and gained a national following — one that might help her win the biggest local election in the country.

New York City is at a turning point. The departure of a two-term mayor — even one as polarizing as de Blasio — is always a major event, but at this point in history the city is in a precarious position for other reasons: Not only has the coronavirus been devastating to the population in terms of its human toll, with over 32,000 deaths and hundreds of thousands more cases, but it has also had a catastrophic impact on New York’s economy. The city lost 631,000 jobs to the pandemic in 2020; restaurants and other businesses shuttered, leaving empty storefronts; the subway lost billions in revenue, cutting service; and at the same time that many wealthy residents left the city, service workers were left to fend for themselves with few government protections. Unemployment and an evictions crisis have served to exacerbate inequality. The Mayor of New York has often been called the toughest job in politics, but never more so than it is now. So, who could possibly want it?

As it turns out, a lot of people — including Wiley. In this heavily Democratic city, many acknowledge that the true mayoral election will take place not on November 2, but on June 22, with the Democratic primary — and there are a lot of people running in that primary, 13 to be exact, including current frontrunners Brooklyn Borough President Eric Adams and former-presidential candidate Andrew Yang. Among this crowded field, Wiley may not stand out for her political experience (or headline-making tweets), but she does for her ambitious, comprehensive plans, including her cornerstone policies, like the New Deal New York, a $10 billion investment meant to reinvigorate the city’s economy at a time when 1.5 million New Yorkers can’t afford food and the unemployment rate is double the national rate. She also has a plan to end the eviction crisis, which affects Black renters at twice the rate of white ones, and an interagency plan to redirect $300 million from incoming NYPD and Department of Corrections Cadet classes toward stipends for informal caregivers. Following a year of massive protests against police brutality and calls to defund police departments, Wiley has also suggested cutting the city’s “bloated” $6 billion police budget by $1 billion a year.

For Wiley, many of these plans, like the one for caregiving, come from a personal place. “I'm a mother,” she says. “My mother was a working mother. And I am a working mother. And so many women carry the burdens both of being breadwinners and caring for family members — literally unpaid work. When I was first thinking whether I should run to be the next mayor of New York City, one of the big factors that was calling me in was the fact that this city is becoming far too expensive for far too many people. And childcare is actually one of the top costs of living in the city.”

After Wiley’s mother developed Alzheimer’s, she suddenly had to care for her, as well as for her two daughters — all while working full-time. “I'm one of the lucky ones, and it was bone-crushing. And so many women, their bones are being crushed every single day. And many of them are struggling and working long hours and still aren’t able to pay the rent, still not able to get the childcare they need, and then COVID hits, right? And women lose a decade of gain in the labor market. Either pushed out in order to help care for their kids who are struggling with online learning, or literally losing a job.”

Wiley has a solid set of ideas aimed toward the monumental task of rebuilding the city after a (hopefully) once-in-a-lifetime crisis. But can she prevail in such a crowded field? The most recent polls show Yang in the lead at 26%, followed by Adams with 20%, city comptroller Scott Stringer with 12%, and Wiley with 10%. Stringer, however, is facing serious and disturbing allegations of sexual assault from former intern Jean Kim, and has been losing support, including major endorsements, which could give Wiley a boost. Of the scandal, Wiley says in a statement: “I believe Kim and admire her strength and courage to come forward to tell her story.” Other still-in-contention candidates include former Sanitation Commissioner and City Hall veteran Kathryn Garcia and progressive, former-nonprofit leader Dianne Morales; some observers speculate that Wiley and Morales are splitting the progressive vote. However, with 14% of likely Democratic primary voters still undecided, and the first debate still to come on May 13, there is still some opportunity to move around in the polls in the coming weeks. And while Yang is benefiting a lot from his name recognition, which is at 76% to Wiley’s 46%, that is already changing as more voters tune in and become more educated on the race in the weeks before the primary: Wiley’s name recognition seems to have jumped by 10% between mid- and late April, while Yang’s has remained virtually unchanged. Another wild-card factor is that this will be New York City’s first primary to feature ranked-choice voting, something that could be important given the crowded field of candidates.

Karen Hinton, a communications consultant and de Blasio’s former press secretary, believes the ranked-choice system could hurt leading candidate Yang, and help someone in Wiley’s position. “I think ranked choice helps defeat Yang, because I think he has a very defined universe of supporters, and then there's everybody else. It's basically white Manhattanites,” Hinton tells Refinery29. “You have a lot of undecided voters. So, when it comes time to choosing your second choice, your third choice, that could help because I don't think Yang will get a majority. Then, that could help push up numbers for the other candidates.” 

Helen Rosenthal, a New York City Council member who has worked for three different New York mayors and who endorsed Wiley back when she announced her run in October, agrees with Hinton that Wiley still has time to make an impression on voters. She also believes Wiley will truly focus on the job, unlike some predecessors.

“Her eye will not be on running for president,” Rosenthal tells Refinery29, referring to de Blasio’s ill-fated presidential run. “Her eye will not be on an intern,” she continues, referring to Stringer’s scandal. “She will be thinking about how New Yorkers experience life and how the city can stand on its own. … A good mayor is thinking about New York City and what’s best for New York City 24/7. They’re eating, breathing, sleeping New York City. You're not thinking about, What is my signature public policy reform that everyone in the nation will think about and think is great? You won't be thinking, like [Michael] Bloomberg, I gotta get out of here on the weekends and go to my private island. You'll be riding the subway. You'll be spending time in all of the very diverse communities.” 

Rosenthal says she remembers running into Wiley at an event for a political club in Morningside Heights about three years ago, where Wiley gave a talk on criminal justice and everyone swarmed around her afterward asking to take pictures. Impressed with her, she asked Wiley then if she had plans to run for mayor. “She said, absolutely not,” Rosenthal recalls. “I remember feeling super-disappointed and just sort of like, ‘Ah, you should really run for mayor!’ And so when she announced, I was just thrilled that she had come to that conclusion herself.” Rosenthal adds that it would be incredibly meaningful if Wiley broke through the “boys’ network” permeating New York City politics.

Were she to win, Wiley would be the first woman mayor of New York City, after 109 men have held the position. She would also be the second Black mayor, after the late David Dinkins. These would be notable accomplishments, so it’s little wonder that her campaign has created a video where Gabrielle Union, Yvette Nicole Brown, and Dr. Brittney Cooper, among others — many of whom are not New Yorkers, attesting to the national attention her campaign has gotten — urge voters, “It’s time to put your money where your mouth is, New York City, and elect the first Black woman to lead this city.”

But exciting as a public statement like that can be, it’s also not enough to win an election, something that Wiley knows well. “Symbolism is not enough,” Wiley said at an event in Brooklyn on April 9. She was surrounded by a couple of dozen members of the Local Employees 1199 of the Service Employees International Union (SEIU), which represents over 200,000 healthcare workers, a key endorsement, and supporters — like Rep. Yvette Clarke — the majority of them Black women. “Calling us queens is not enough. Recognizing we are qualified is what we demand.” She continued, gesturing around her, “These women put me through my paces — [they said,] ‘I don’t want to hear that you care, I want to hear that I’m going to be able to pay the rent, and when I pull the dollars out of my pocket there’s something left over to buy food.’”

Clarke, wearing a pink suit and flashing the Delta Sigma Theta sorority sign (both she and Wiley are members), formally endorsed Wiley, and spoke of the historical importance Wiley’s leadership would take. “We have a unique opportunity here in the city of New York to make a difference and to join the ranks of such cities as Atlanta, New Orleans, Boston, and Washington, D.C., where Black women have taken the helm and have demonstrated confidence, ability, and compassion,” Clarke said. Rita Joseph, a New York City Council candidate, echoed Clarke when speaking to Refinery29, “New York is such a progressive city; we need to lead by example. Normally we do, but we haven’t.” 

It’s hard to overstate how important it would be to have a Black woman — one who intimately knows the plight of working mothers in this city, because she is a working mother; one who doesn’t only prioritize the needs of Manhattanites, because she lives in an outer-borough — as New York’s 110th mayor. Wiley's leadership feels like it could change everything, even as it could also signify a prioritization of the kinds of things people have always cared about most: friendship, family, and connection. When asked what helps ground her as the race heats up and among a fraught news landscape, Wiley brought up her family, as well as regular Saturday night Zoom gatherings with a group of friends where they talk and support each other. After the Clarke event, Wiley walked home — she lives in Prospect Park South — to her husband, daughters, and four cats for some much-needed family time. “We protect family dinner, so we have a family dinner every night.” Now, she is cherishing those close to her as major parts of her campaign, hoping these very things will help her rise to the top so she can implement her plans to strengthen New York City and take it in a more equitable direction.