Maya Wiley (photo: John McCarten/City Council)

[This article is part of a series on the leading Democratic mayoral candidates' strengths and weaknesses.]

Maya Wiley has an extensive and diverse resume, working inside and mostly outside of government, but has never run for office before this year, when she is seeking to become the first woman and second Black person ever elected Mayor of New York City.

Undoubtedly in the top tier of the crowded Democratic field hurtling toward the June primary likely to decide the next mayor, Wiley has raised a significant amount of money and qualified for millions in public matching funds, received a number of important endorsements, and is widely considered among the candidates most likely to win, though perceived to be behind the better-funded and more-known Andrew Yang, Eric Adams, and Scott Stringer, while others are hopeful they can surge in the final months.

Like all candidates, Wiley comes to the race with various strengths and weaknesses that will help determine whether she can successfully convince enough voters to select her in their top two or three through the first citywide use of ranked-choice voting and carry her to victory in the increasingly intense primary. The first goal, of course, is to be ranked first by as many voters as possible.

A civil rights attorney and former counsel to Mayor Bill de Blasio, Wiley has been running an assertive campaign with a team of veteran political operatives, though she often falls back on vague talking points, values statements, and lawyerly ambiguity. As a first-time candidate for elected office she offers herself as a straight-talker yet regularly appears unwilling or unable to say what she really thinks about a particular issue or what she would specifically do if elected. But Wiley has run as an underdog with confidence, built on decades of experience working on the thorniest issues in American society and fighting for equity that isn’t easily attained, power that isn't easily ceded.

She has been rallying Black women, especially, while assembling a multi-racial coalition of powerful labor unions and elected officials that includes the 1199 SEIU health care workers and U.S. Representatives Nydia Velazquez and Yvette Clarke. A former MSNBC legal affairs contributor, Wiley is a compelling and compassionate public speaker who knows how to read a room, even on Zoom, and has sought to differentiate herself in the field as the progressive candidate most in touch with the 'pain and purpose' of communities of color — though she has competition in that regard from former nonprofit executive Dianne Morales.

The challenges Wiley faces are significant: she must introduce herself to many more voters with relatively limited funds and separate herself from candidates who have stronger public brands or long-held elected office by making her vision for the city and positions on key issues more clear and offering a more commanding narrative around why she should be the next mayor — right now, she most often says she’s running to make New York "a city where everyone can live with dignity.” She must land her attempt to play the insider/outsider who spent enough time in city government to know it well but not so much that she’s part of the status quo or old guard, and in doing so she must separate herself from her former boss, de Blasio, while also appealing to those, especially Black voters, who still support the outgoing mayor. She must convince left-leaning Democrats disillusioned with de Blasio that she wouldn’t also disappoint them by being too weak or ineffective or distracted.

Wiley must persuade a broad enough overall coalition, that for her to win must include large swaths of both Black voters and progressive white voters, in similar fashion to the central coalition that helped de Blasio prevail in the crowded 2013 primary, though he was also buoyed by a significant number of Latino and Orthodox Jewish voters in getting just over the 40% threshold needed in past primaries to avoid a run-off.

Wiley comes from a family of civil rights activists, and she followed in their footsteps with a focus on issues of racial justice and police reform. She began her career with the NAACP Legal Defense Fund in 1992, working there for two years before joining the civil rights division at the office of the U.S. Attorney for the Southern District of New York, where she served for three years between 1994 and 1997. She then was a senior adviser on race and poverty at the Open Society Foundations till 1999. In 2002, she co-founded the Center for Social Inclusion, a national nonprofit organization dedicated to combating racial inequity. Twelve years later, in 2014, she was hired by de Blasio to act as his counsel and administration lead on key initiatives, work she did for two-and-a-half years before departing and being named by de Blasio as chair of the city’s Civilian Complaint Review Board (CCRB), a police oversight agency. She led the body for just over a year and resigned to prioritize her position at The New School, where she taught and served as senior vice president for social justice.

On the mayoral campaign trail, Wiley often mentions aspects of her resume but rarely notes any particular accomplishments. In her time at City Hall and the CCRB, she led on several racial equity and justice priorities but was also embroiled in some controversy.

For the de Blasio administration, she spearheaded efforts to expand internet broadband access, which she continued to work on as co-director of the Digital Equity Lab at The New School. She also helped the city increase contracting awarded to Minority- and Women-Owned Business Enterprises (MWBEs). She continued in a similar vein as she focused on police accountability and reform at the CCRB.

But as de Blasio’s counsel she advised him on two matters that became a stain on the mayor’s record, one involving his solicitation of donations from entities with city business and the other his shielding communications with outside political advisors (some of whom had business or clients with business before the city), whom she dubbed “agents of the city.”

A handful of people who worked with Wiley when she was at City Hall generally described her as committed, caring, collegial, and productive, while two described her as slow to execute. Wiley has admitted a sense of being in over her head initially when taking on the broadband project, given her lack of familiarity with city government and the nuts and bolts of the issue itself, though on the mayoral campaign trail she regularly touts what she was able to accomplish on the subject in a relatively short amount of time and blames de Blasio’s leadership for not going further to get more New Yorkers connected to the internet at home.

But it’s not Wiley’s government service or her academic experience that brought her national attention. She gained prominence on MSNBC, earning her a large social media following and popularity among the channel’s (mostly white) progressive audience. In one particularly viral moment, Wiley convinced former Donald Trump aide Sam Nunberg, who appeared in desperate straits while on air, to testify in Special Counsel Robert Mueller’s investigation into Russian interference in the 2016 presidential election rather than refuse a subpoena and risk jail time. She was widely praised for her show of humanity toward Nunberg, displaying an empathy that is at the center of her mayoral campaign.

Her MSNBC presence and her background doing civil rights work helped Wiley develop a national network that has boosted her fundraising, though only contributions from city residents are eligible for matching funds. Wiley has had among the top totals for number of individual donors, both overall and from within the city.

When Wiley jumped into the race in October, she shook up a field that was just beginning to form and which continued to grow thereafter, most notably with Yang’s January entrance.

“The theory of the case, originally, was that Maya could really be almost kind of a unicorn candidate,” said Neal Kwatra of Metropolitan Public Strategies. “She's super smart, very compelling. She understands how to communicate to the public, given her experience on TV. I think one of the things that she's going to still need to do that I don't think we've seen entirely yet is make that emotional connection with voters and sort of talk to voters more broadly about what her motivation is, and what her story is, and why, after everything she's done in her life...why does she now want to try to lead the largest city in the country? What is it about her background that not just motivates her but prepares her?”

What at times appears to hold Wiley back is her cautious instincts and measured approach to policy and hot-button issues. She has issued detailed plans on gun violence, a New Deal-type jobs program, avoiding an eviction crisis, and expanding and funding the “care economy” that largely employs women of color. But she has often hedged her positions on several other issues, perhaps most notably the sweeping recommendations of a school desegregation task force that she co-chaired at de Blasio’s request. Asked repeatedly whether she is making the recommendations part of her campaign platform, Wiley has been evasive and only gone as far as to say she stands by them — she has yet to release a full education plan. Her refusal to take a conclusive stance on some issues has allowed candidates like Morales, Stringer, who is the city comptroller, and former federal housing secretary Shaun Donovan to outflank her on the left or simply provide more clear answers to those who may be watching a particular candidate forum or interview.

“She is certainly a contender, but not a top contender,” said George Arzt, a veteran Democratic consultant. Arzt noted Wiley’s tendency to speak in talking points rather than substance. “I find that she doesn't talk in policy...I think with a little bit of help on policy, and on getting a strong policy point of view out, she could do well,” he said, arguing she needs to become known for ideas beyond her strong focus on police reform issues, something Wiley has attempted to do with her “New Deal New York” and “care economy” plans.

Some see her measured approach, in combination with other characteristics, as a strong positive. “She has a temperament that is able to explain complex issues to voters in a way that has a level of intellect and compassion behind her explanation, which has been missing in our politics on the local, state, and federal levels for so long,” said Dr. Christina Greer, political science professor at Fordham University. “One of the two has always been missing or both. So I think that that's what's attracting voters to her, is that combination of intellect and compassion.”

Wiley has repeatedly distanced herself from de Blasio, often criticizing his failure of leadership and the many unfulfilled progressive promises of his two terms. It’s unclear how much dissatisfaction with de Blasio could taint her campaign, or to what extent the association could be helpful, especially among the Democratic primary voters who believe the two-term mayor has fought for them. Repeatedly asked about it, Wiley has over and again said she “stands on her own two feet” and is her own person with her own candidacy. She says she’s proud of her work at City Hall but that she also “voted with my feet” to leave the administration when she felt that she was bumping into a “brick wall” in terms of not being able to advance priorities.

In the spotlight for some, likely a relatively small number of close-watching politicos, is the controversial defense Wiley offered of the mayor’s attempt to hide his communications with outside advisors from public disclosure and the role she played in shaping his line-blurring efforts to raise funds for a nonprofit he formed to promote his agenda, which landed the mayor under federal investigation. Both are the sorts of ethical matters that are usually of more concern to the press and good government groups than to the masses.

Wiley had termed the outside advisors “agents of the city,” a shaky legal argument that was eventually rejected by a court that ordered the emails released after the New York Post and NY1 sued the administration under the Freedom of Information Law. The emails were more revealing and embarrassing than evidence of improper behavior, but nonetheless were a black eye for the mayor, part of an association with Wiley remembered by political insiders.

The mayor’s fundraising for his nonprofit was far more scandalous, leading to local, state, and federal investigations, though the mayor was never charged with any crime. Wiley, as de Blasio’s top government lawyer, advised him on how to raise funds without violating ethics regulations but the mayor still ended up in hot water. Though he faced no charges, the Manhattan District Attorney chastised him for bending the rules by raising funds from people with business before the city and the city Department of Investigation later condemned him for it. In recent reporting by The City, Wiley’s campaign laid the blame at the mayor’s feet, saying he failed to follow her advice.

“Maya Wiley is smart and capable and often stood her ground when she worked for Mayor de Blasio, but she lacks the hands-on experience that Scott Stringer has had in various roles,” said Karen Hinton, a communications consultant and former press secretary to de Blasio who overlapped with Wiley in City Hall. “Unfortunately, she was the legal mastermind behind the agent-of-the-city fiasco that failed to stop the public release of emails to Mayor de Blasio from non-employees. That said, if elected, she will hit the ground running and learn fast.”

“I don't think the de Blasio connections are all that problematic, frankly,” said Kwatra. “I just don't think voters are going to really attach her [to the mayor] that much, partly because she was there for such a little amount of time. That is not remotely a defining part of her career experience.”

For her part, Wiley has mostly critiqued de Blasio in very clear terms, though selectively. "What's wrong has not been mayoral control, it's been the mayor himself," she said about control of city schools at a candidate forum hosted by the union of principals and school administrators. At her campaign launch, Wiley gave a clear if oblique rebuke to de Blasio, saying New Yorkers would not have to worry about her being off in Iowa if she’s elected to succeed the mayor who quixotically ran for president for five bizarre months in 2019.

More central to her campaign strategy, Wiley is making an overt aggressive effort to court Black women, who vote in greater numbers and form the foundation of the Democratic electorate, as part of an appeal to the same voters who helped elect de Balsio in the last open mayoral race, in 2013. She was also endorsed by 1199 SEIU, the city’s largest union, which represents more than 200,000 health care workers who are mostly women of color. The union played a crucial role in elevating de Blasio in the 2013 primary. 

Wiley is one of many first-time candidates and she does not have a deep record of government service to show New Yorkers. Counsel to the mayor is not the type of public-facing job that lends itself to voter recognition. But that also means she does not have a lengthy public policy or voting record to defend. “For any first-time candidate, you can't point to a record [as an elected]. It's all prospecting, as far as what you plan to deliver,” said Dr. Greer. “So whereas people who have been in office, even though that could be a double-edged sword, they can at least take these various policies that they've helped implement, or loyalty,” based on what the public may be familiar with them for doing.

Candidates like Wiley, Donovan, who served for all eight years of the Obama administration and previously as city housing commissioner under Mayor Michael Bloombeg, and Kathryn Garcia, a former city sanitation commissioner under de Blasio, have all worked in government (Wiley much less so than Donovan and Garcia) and have accomplishments to point to, but not as elected officials, so they are attempting to both introduce themselves to voters and stake claim to what they did in government in someone else’s name.

“And obviously, she's trying to distance herself from her time with de Blasio,” Dr. Greer said of Wiley. “So her time in government is somewhat limited in her political narrative.”

But Wiley does tout her work on broadband, MWBE contracting, and police accountability, while she and her surrogates also paint her lack of elected experience as a strength, not a weakness. Former Bronx Assemblymember and DNC vice chair Michael Blake said Wiley has “room for growth” in pitching herself as a candidate who can lead the city.

“There is the constant validation question that you have to answer where others, because they are in office, are presumed to be better for office. That is a challenge. That is an absolute challenge. No question,” said Blake, who endorsed Wiley at the time of her campaign launch. Stringer and Adams, the Brooklyn Borough President who is Black and counting on wide support among the city’s Black voters, are the only elected officials in Democratic primary field.

But, Blake insisted, “If you are going to be the most well-funded and well-known woman, and particularly a woman of color in the race, I think that's a pretty solid standing point to begin with. And I think while the others have been elected, being elected is not enough.”

Blake said Wiley has the greatest “floor to raise up” with the ability to build a coalition of women and people of color, who will be the most likely engaged voters in the primary. “I do think when you look at what is going on in the city and in the country, there is a desire for new leadership,” he said. “Her strength of her background of what she did on MWBE issues, her work on criminal justice, I just believe it's going to create a greater argument of equity than the others.”

The 1199 endorsement will also carry extra weight this year, Blake said, in the wake of the pandemic. “People are listening to the health-care heroes, they still are. And if someone helped to save your life, if someone helped to provide care for your loved ones, I think that’s gonna be a pretty strong validator when you're talking about who should be your next mayor,” he said.

A prominent two-sided issue in this year’s election is the matter of public safety and policing, including the size of the NYPD’s budget and what responsibilities police officers are tasked with. While the crime rate fell overall last year, murders and shootings skyrocketed amid the COVID-19 outbreak and its many impacts, leading to calls for greater investments in policing. But activists have been pushing to “defund the NYPD” since negotiations over last year’s city budget and for greater accountability for police misconduct.

Having led the CCRB, Wiley expresses strong support for ensuring that abuse of power by officers does not go unpunished, and she has said she would institute a culture change at the NYPD. After the department’s violent crackdown on the Black Lives Matter protests last year, she called on the mayor to fire Police Commissioner Dermot Shea. She’s proposed a plan that would modestly reduce the size of the police and corrections forces and use the funds saved to invest in her “Universal Community Care” and “Care Income” proposals. While her plan could win her votes on the left, it could lose her support from moderates, even in Black communities, for whom public safety is a top priority and there were limited calls for defunding the police last year, as explained by a number of Black City Council members during the budget process, which did strip some funding and responsibilities from the police department, but nowhere near what activists, many of whom are Black, were calling for.

“CCRB I don't think can be ignored,” Blake said of her time leading the agency. “I think if you're talking about how do you build the bridge between the community and officers, how can someone say they have better experience than she does in that area?”

Wiley’s record on the CCRB isn’t as clear cut, however, when it comes to the most high-profile police misconduct case of her tenure. On the campaign trail, she has taken credit for the CCRB investigation that eventually led to the firing of NYPD Officer Daniel Pantaleo, who choked Eric Garner to death on Staten Island in 2014. But the CCRB investigation took three years to complete – its recommendations were made public in September 2017, a week after Wiley’s resignation from the agency – and Pantaleo wasn’t fired until 2019, five years after Garner’s death. Wiley has said that, if she was mayor, she would have fired Pantaleo sooner while also supporting full repeal of a law that shielded officer disciplinary records at the time. It does appear that the CCRB had little choice but to wait for the conclusions of legal proceedings being conducted at the state and federal levels to really move ahead with its Pantaleo investigation.

Wiley has been careful about how she discusses her police reform platform. For instance, while she regularly talks about moving some funding away from the NYPD, including through a small reduction in the uniformed headcount, she has not put a dollar figure on it and she has declined to use the “defund” terminology, and said at a recent mayoral forum that she would have elevated police officers who did their job well during the protests last year.

Wiley’s answers to questions about policing and NYPD funding often show her limited willingness to open up about what she would do as mayor in a detailed way.

City Council Member Helen Rosenthal, an Upper West Side Democrat who has endorsed Wiley, also said the city is ready for new blood. “You know how the definition of insanity is doing the same thing over and expecting different results? She’s not that,” she said of Wiley. Citing her own experience of having worked in the mayor’s Office of Management and Budget under Mayor Michael Bloomberg before she became a Council member, Rosenthal said, “I've seen how mayors who are not the everyday typical Mayor can actually make a difference.”

“But I do recognize that you have to break out of the box. We're stuck in a white man’s box that  maybe 50 years ago we wanted to stay in. But the cry of New Yorkers is for meeting the moment,” Rosenthal added. 

Rosenthal’s critique of the current power structure was both personal and societal, as she alluded to the recent sexual harassment allegations against Governor Andrew Cuomo, whom Wiley was assertive in calling to resign.

Closer to home, Mayor de Blasio in recent years has been accused of ignoring sexual harassment in his administration and of being dismissive towards the women he appointed in leading positions. Wiley herself relayed such an anecdote in a recent New York Magazine story, recounting how her attempt to talk about outreach to Black communities for the implementation of universal pre-kindergarten was “steamrolled” in a senior cabinet meeting. After a complaint against her, she was later upbraided by the mayor “for my behavior in senior Cabinet and for being divisive,” she said.

“Look at the daily barrage of how men treat women as their second nature and all the people around them who enable it, wittingly or unwittingly,” Rosenthal said. “As someone who has faced a lifetime of dealing with this, I'm ready for somebody who doesn't think that way is OK and has never been part of that culture.”

She also contrasted Wiley’s leadership style with de Blasio, who was known for micromanaging and undercutting the very experts he appointed to city agencies in favor of following his own, often flawed, instincts. “I always look for people who don't clip the wings of the people around them, but instead let them fly,” Rosenthal said.

Wiley and her campaign have in recent weeks shown sharper elbows toward Yang, the entrepreneur and former presidential candidate who disrupted the mayoral race with his poll-leading entrance at the start of the year. At one of many Zoom forums, Wiley confronted Yang about reports of a misogynistic culture in his presidential campaign, and a campaign spokesperson recently called Yang a “mini-Trump” over a lack of preparation for the job of mayor. Wiley has critiqued Yang for a lack of qualifications and other forms of readiness, and sought to highlight key differences in how they approached what should happen with federal stimulus money headed to the city. While Yang cautioned against using it too quickly or inefficiently, Wiley said it must be used as intended, as stimulus, and to invest in New Yorkers.

Wiley and her campaign clearly know that with just over two months until primary day, June 22, she will have to beat or compete well with Yang among certain demographics, especially white progressives, and that while he is more popular with men than women, she is counting on women to help her win the nomination. Early polls have shown Yang as the clear frontrunner, followed by Adams then Stringer, and Wiley in apparent fourth place, though she has shown up closer to the rest of the pack, and 50% of likely voters were undecided in one recent survey, showing the wide open and fluid nature of the race.

Wiley also finds herself behind Adams, Stringer, Yang, Donovan, and former Wall Street executive Ray McGuire in fundraising, though the imminent public funds payout and mid-April filing will tell at least a somewhat new story. Still, Wiley may have millions of dollars less than several other candidates for the stretch run and need to rely on other strengths to take off, if she’s going to.

“It is clear that Maya is building a diverse coalition from communities from across the 5 boroughs and is gaining momentum every day,” said Julia Savel, a campaign spokesperson, in a recent statement. “Through her history as a champion for all New Yorkers and her time at the ACLU and the NAACP uniquely position her to bring new representation and ideas to City Hall. With endorsements from 1199SEIU, Congresswoman Nydia Velázquez, and a diverse group of state legislators and city councilmembers, it is clear that a citywide movement is happening on Maya's campaign.”

[This article is part of a series on the leading Democratic mayoral candidates' strengths and weaknesses.]

Ben Max contributed to this story.

[WATCH: Maya Wiley Discusses Her Run for Mayor]

[LISTEN: Max & Murphy Podcast: Maya Wiley Runs for Mayor]