Ms. Wiley has unveiled an array of policies to fight inequality as she seeks to become the first woman elected mayor of New York. Can she break out of the pack?

The New York City mayoral race is one of the most consequential political contests in a generation, with immense challenges awaiting the winner. This is the fourth in a series of profiles of the major candidates.

By Emma G. Fitzsimmons

If there was a single moment that captured the essence of Maya Wiley’s campaign for New York City mayor, the Women for Maya launch was it.

She sat on a folding chair in Central Park at the event earlier this month, at the foot of a statue depicting three historical figures of women’s suffrage. To her immediate right was Representative Nydia Velázquez, the first Puerto Rican woman elected to Congress; to her left was Gloria Steinem, the feminist icon.

Since entering the mayor’s race last year, Ms. Wiley had underscored how it was time for a woman — a Black woman — to finally lead New York, someone who understood the concerns of those who struggled even before the pandemic and who are worried that the recovery is leaving them behind.

“You will no longer tell us we are not qualified,” Ms. Wiley said, before starting to chant “We lead!” with a crowd of supporters who gathered at the event.

Ms. Wiley, 57, offers a mix of experience — she served as a former counsel to Mayor Bill de Blasio and led the Civilian Complaint Review Board — and a dose of celebrity: As a prominent analyst for MSNBC, she won the attention of its left-leaning viewership and sparked enthusiasm that she could become the standard-bearer for New York’s progressive left.

Her comfort level with the on-the-fly jousting seen on cable news shows seemed to give her an advantage last week in the first official Democratic debate, as she repeatedly challenged Eric Adams, the Brooklyn borough president who is one of the contest’s front-runners.

Three days later, she landed a key endorsement from Representative Hakeem Jeffries, the state’s highest-ranking House member. His support is expected to help Ms. Wiley with a key constituency Mr. Adams is also vying for: Black voters, especially from central Brooklyn.

If Ms. Wiley has a path to victory in the June 22 primary, it will also largely be paved by women. She has the support of the city’s largest labor union, Local 1199 of the Service Employees International Union, which represents 200,000 health care workers, many of whom are women of color. And she has the backing of Ms. Velázquez and Representative Yvette Clarke, two powerful congressional leaders in Brooklyn.

She hopes to capitalize on the sexual misconduct allegations that were recently lodged against her chief rival for progressive voters in the Democratic primary, Scott M. Stringer, the city comptroller; Ms. Wiley called on Mr. Stringer to withdraw from the race, and she has picked up some of the endorsements he has lost.

Her campaign is centered on a series of policy proposals that reflect her progressive values. She wants to cut $1 billion from the police budget and trim at least 2,250 officers. She wants to help poor families pay for child care by offering $5,000 grants to caregivers and building community centers with free child care. And she wants to create a $10 billion Works Progress Administration-style jobs program that funds infrastructure repairs and other projects.

But she has yet to fully energize the left-wing of the party that she is trying to win over; she upset some activists by distancing herself from the defund the police slogan; she can also sound at times like her former boss, Mr. de Blasio, whose popularity has fallen sharply in his second and final term.

Unlike Mr. Stringer and Mr. Adams, who have said they had always wanted to be mayor, Ms. Wiley readily acknowledges that running for office was never a lifelong ambition. She says she long believed she was more effective, and more natural, at pressuring elected officials from the outside.

“I literally never thought I would run for public office, and I mean never,” she said in an interview. “It was not on my bucket list. I’ve been a civil rights lawyer and advocate my whole career, and politics is not appealing. What I wanted to make was change.”

She said that her outlook began to shift several years ago, when her teenage daughter came to her almost in tears, worried she would be unable to pay rent in New York City while pursuing a career as a graphic novelist and illustrator. Ms. Wiley said the exchange brought home how increasingly unaffordable the city had become.

“That was an emotional gut-punch moment that really stayed with me,” she said.

While politics was not necessarily in Ms. Wiley’s blood, a commitment to social justice was.

At the event in Central Park, Ms. Steinem spoke about working with Ms. Wiley’s father, George Wiley, a prominent civil rights activist, in the 1970s.

He founded the National Welfare Rights Organization and paid attention to “women in poverty as the single most important indicator of the country’s welfare when no other male spokesperson was doing that,” Ms. Steinem said.

“I’m so sorry that Maya lost him young, but his spirit is in her,” she said.

‘We had to find a way to live’

The sudden death of Ms. Wiley’s father was especially traumatic.

Mr. Wiley had taken his two children, Daniel and Maya, sailing off Chesapeake Beach, Md., on a summer day in 1973. The winds and seas were rough, and Mr. Wiley fell from the 23-foot pleasure craft into the Chesapeake Bay.

His children threw him a line, but the tides and wind pulled him away, according to an Associated Press account of the episode. Days later, memorial services for Mr. Wiley, 42, were held across the nation.

Ms. Wiley often speaks of her father’s death as a formative experience that shaped her and taught her a hard lesson in grief and perseverance. At her campaign kick-off event on the steps of the Brooklyn Museum in October, Ms. Wiley compared her loss to families who had watched a relative die from the coronavirus and could not hold them one last time.

“My brother and I — two little kids, 9 and 10 years old — alone on a boat after watching the waves wash away our father, we had to find a way to live,” she said.

She described how they found their way to the shore, and how the white beachgoers they encountered did not help them. They went from house to house asking for help until someone called the police.

The seeming indifference from the people on the beach stayed with her. The experience, she told Bloomberg Opinion, made her realize that “racism is a deep illness.”

Other parts of her biography often come up on the campaign trail. Ms. Wiley’s mother, Wretha, grew up in Abilene, Texas, and came to New York to attend Union Theological Seminary. Her parents met at Syracuse University and moved to the Lower East Side, where Ms. Wiley lived briefly as a baby, before they left for Washington.

When she talks about education, Ms. Wiley notes that attending a segregated school as a child informed her thinking on the issue. She led a high-profile school diversity panel that in 2019 called for integrating city schools by eliminating gifted and talented programs.

Yet when she is asked about fixing the city’s segregated school system, she has been vague at times, seeming cautious and political. Asked if she was afraid of talking about a combustible issue, Ms. Wiley pushed back.

“I’m a kid who went to a segregated Black elementary school when I was young and was two years behind grade level despite the fact that my parents had collectively over eight years of graduate education between them,” she said.

“I’m not afraid of third rails,” she added. “I wouldn’t be running for mayor if I was.”

After her father’s death, Ms. Wiley moved to a private school where she caught up with her peers. She graduated from Dartmouth College and Columbia Law School. As a young lawyer, she worked as a staff attorney at the NAACP Legal Defense and Educational Fund for two years, as an assistant U.S. attorney for the Southern District of New York for three years and at the American Civil Liberties Union as part of a fellowship.

The job she held the longest was at the Center for Social Inclusion, a nonprofit she founded after the Sept. 11 attacks as a young mother “sitting in my living room with a baby in a bouncy seat.” She built it into a national organization dedicated to addressing racial inequity, with a $3 million annual budget and 13 employees.

“As she came into her own, she opted not to go to a big private law firm, but to commit herself to public service,” said the Rev. Al Sharpton, who expressed admiration for Ms. Wiley’s dedication to social justice when she could have taken a different path. “She was progressive before the term was fashionable.”

A rocky experience inside city government

Ms. Wiley had never met Mr. de Blasio when she wrote a piece for The Nation magazine about broadband internet access that caught his attention. He invited her to three long get-to-know-you meetings at City Hall.

She had been in the running to lead the N.A.A.C.P., but agreed to join Mr. de Blasio’s administration in 2014 as his chief legal adviser. She was proud to be the first Black woman to hold the job, and joked early on that her main goal was to “keep him out of jail.”

Ms. Wiley, even in jest, was somewhat prescient: Mr. de Blasio was investigated for questionable fund-raising practices, leading Ms. Wiley to help craft the administration’s legal response. She also became known for her role in what became known as the “agents of the city” controversy, when she argued unsuccessfully in 2016 that Mr. de Blasio’s emails with outside advisers should be private.

Ms. Wiley helped form Mr. de Blasio’s argument that communications with outside advisers should be as immune from public scrutiny as those of any city employee, even though many of the advisers also represented clients with business before the city.

John Kaehny, executive director of the good-government group Reinvent Albany, said the efforts to hide the mayor’s emails were “desperate, doomed and destructive” and undermined Freedom of Information laws and ethics rules.

“Agents of the city was a giant blunder by her and de Blasio and hopefully she learned from her mistakes,” he said.

Ms. Wiley has gone to great lengths to say that her administration would be more transparent than Mr. de Blasio’s. She says that it was her job to provide the mayor with legal advice and it was his decision whether to follow that advice.

Understand the N.Y.C. Mayoral Race

• • Who’s Running for Mayor? There are more than a dozen people still in the race to become New York City’s next mayor, and the primary will be held on June 22. Here’s a rundown of the candidates.
  • What is Ranked-Choice Voting? New York City began using ranked-choice voting for primary elections this year, and voters will be able to list up to five candidates in order of preference. Confused? We can help.

  “Those emails would have been public if I was the decision maker,” she said at a mayoral forum.

  Not long after the episode, Ms. Wiley resigned and became chairwoman of the Civilian Complaint Review Board, the agency that investigates police misconduct.

  While Ms. Wiley points to her time there as valuable experience in learning how to tackle police reform, groups like the New York Civil Liberties Union say she was too secretive about the disciplinary process and too sluggish in confronting the Police Department. The current chairman, the Rev. Fred Davie, has been more outspoken on issues like repealing 50-a, a law that until recently kept officer disciplinary records secret.

  Her experience at City Hall and the watchdog agency has enabled Ms. Wiley to argue that she knows city government, but it also ties her to Mr. de Blasio.

  Ms. Wiley, like Mr. de Blasio, has been known to speak about inequality in broad terms. When she described homelessness as a public safety issue during a recent appearance on Brian Lehrer’s WNYC show, Mr. Lehrer shared a response from a listener: “de Blasio 2.0.”

  Ms. Wiley argues that women should not be judged by the men they worked for. She praised Mr. de Blasio’s achievements like universal prekindergarten and criticized him over his handling of the police killing of Eric Garner in 2014.

  “Women should not be defined by anything other than their record,” she said. “I’m not running against Bill de Blasio.”

  A push to ‘reimagine’ New York

  As protests over police brutality rocked the nation last summer, Ms. Wiley gained attention on MSNBC for her clearheaded explanations of why some activists wanted to defund the police.

  Her national exposure created excitement when she entered the race, but also the expectation that she would catch fire as the leading progressive candidate. That has not happened for a variety of reasons.

  “This is a race that has a lot of progressive options,” said Eric Phillips, a former press secretary for Mr. de Blasio. “I think it’s natural that there would be real competition and one candidate wouldn’t automatically own that lane.”

  Ms. Wiley must prove that she can energize the left-wing of the party and be the most viable candidate to take on the two more moderate front-runners, Andrew Yang, the former presidential hopeful, and Mr. Adams. She is often in third or fourth place in the polls, along with Mr. Stringer.

  But the accusations lodged against Mr. Stringer have created some room for momentum: The powerful Working Families Party had named Mr. Stringer as its first choice for mayor, but withdrew the endorsement after the sexual misconduct allegations. The group is now supporting Ms. Wiley and Dianne Morales, a former nonprofit executive and the most left-leaning candidate in the race.

  Still, Mr. Stringer has a major fund-raising advantage: He has more than $7 million to pour into television ads. Ms. Wiley has about $2.5 million on hand.

  Mr. Sharpton said he believed that Ms. Wiley could make a “late surge” once more voters start tuning into the race. He is considering endorsing one of several of the candidates trying to become the city’s second Black mayor — Ms. Wiley, Mr. Adams, or Raymond J. McGuire, a former Wall Street executive — if Mr. Sharpton believes he could help one of them win, according to a person who is familiar with his thinking.

  To differentiate herself from some of her rivals, Ms. Wiley has been rolling out her “50 Ideas for NYC,” a new plan every day focused on issues like reducing the Black maternal mortality rate. Her most ambitious proposal is called “New Deal New York,” which involves spending $10 billion to help the city recover from the pandemic and to create 100,000 jobs. Her universal community care plan would make 100,000 families eligible for a $5,000 annual grant to care for children and older people. She also wants to hire 2,500 new teachers to lower class sizes.

  As concerns have grown about violent crime, she released a policing and public safety plan that includes hiring a civilian police commissioner and creating a new commission to decide whether to fire officers accused of misconduct. She was early in urging Mr. de Blasio to fire his police commissioner, Dermot F. Shea, after his aggressive response to last year’s protests.

  Yet she has also distanced herself from the defund slogan, saying the term “means different things to different people.” In contrast, Ms. Morales has embraced the movement and pledged to slash the $6 billion police budget in half — a stance that has endeared her to left-leaning voters, less so to more moderate ones.

  At the same time, some business and civic leaders fear that Ms. Wiley is too liberal; in a poll of business leaders, Ms. Wiley was near last place with just 3 percent. They also question whether Ms. Wiley has enough experience as a manager to run a sprawling bureaucracy with a $98 billion budget.

  “Maya is terrific, but business is looking for a manager, not an advocate,” said Kathryn Wylde, the leader of a prominent business group.

  At the moment, Ms. Wiley is simply looking to connect to as many voters as she can, in person and on social media, where she posts campaign diaries recorded at home.

  She lives in Ditmas Park, Brooklyn, with her partner, Harlan Mandel, in an elegant house built in the Prairie School architectural style made famous by Frank Lloyd Wright. They have two daughters, Naja, 20, and Kai, 17. Ms. Wiley is Christian and Mr. Mandel is Jewish, and they belong to Kolot Chayeinu, a reform congregation in Park Slope.

  The last woman who came close to being mayor, Christine Quinn, a former City Council speaker, said she regretted that she tried to soften her hard-charging personality during her campaign. Her advice for Ms. Wiley was to be herself.

  “The thing voters hate the most is someone who is not authentic,” Ms. Quinn said. “Maya needs to be exactly who she is.”

  Who Ms. Wiley is, she said in an interview, is the daughter of civil rights activists who will fight to make the city more fair.

  “I have been someone committed to racial justice and transformation my entire career,” Ms. Wiley said. “And that means bringing us all back, every single one of us, and not just back to January 2020, but to reimagine this city.”

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