Who might contend to be Herroner in 2021?

As the top tier of 2021 New York City mayoral candidates begins to solidify – among them two borough presidents, the New York City comptroller and City Council speaker – one commonality is obvious: They’re all men. The two women in the race so far, Bronx nonprofit director Dianne Morales and contracting company CEO Joycelyn Taylor, lack name recognition and political experience.

That’s not to say strategists, consultants and political veterans are ruling out the possibility of New York City’s first “herroner,” tossing out names like veterans of New York City Mayor Bill de Blasio’s administration Maya Wiley and Alicia Glen, former City Council Speakers Christine Quinn and Melissa Mark-Viverito, and former City Councilwoman Eva Moskowitz.

But while observers say these women could shake up the race if they got in it, it’s crickets so far. Of the group, only Moskowitz and Glen responded to our request for comment – with a definitive “no comment.”

Experts on the involvement of women in politics say the dearth of competitive candidates isn’t surprising, considering women are underrepresented in New York City’s elected offices, including the City Council. Currently, only 12 of the 51 City Council seats are held by women.

“You don’t have people standing at bat waiting to come up and swing,” said Liz Abzug, daughter of 1977 mayoral candidate and former Rep. Bella Abzug, and president of the Bella Abzug Leadership Institute, which provides young women with professional mentoring. “And unfortunately, because of the intensity of this race and the powerful interests that one has to deal with – while connecting with very varied constituencies in five boroughs – it is very tough.”

“You have to start running now, running all over the boroughs.” – Manhattan Borough President Gale Brewer

Ravi Gupta, co-founder of Arena, a consultancy that worked with challengers to Albany’s Republican-aligned Independent Democratic Conference in 2018, also identified filling the mayoral pipeline with women in local office as the long-term answer to gender parity in City Hall. “It’s our responsibility to help support as many women as possible running down-ticket,” Gupta said. “That’s obviously the bench for higher office.”

Though the election is still two years away, insiders agreed that whoever jumps in must do so soon. “You have to start running now, running all over the boroughs,” Manhattan Borough President Gale Brewer told City & State. (Brewer herself has been approached to run for mayor – “people are very kind, they ask me all day long” – but says she won’t. She is reportedly considering a return to the City Council.)

Among the men, New York City Comptroller Scott Stringer and Brooklyn Borough President Eric Adams have yet to officially announce, but have been fundraising competitively. Bronx Borough President Ruben Diaz Jr. filed to run in July 2018. New York City Council Speaker Corey Johnson announced in January he was exploring a run for the office. (New York City Public Advocate Jumaane Williams has been rumored as one potential late entrant.)

Fundraising is one major reason to jump in early. Although she’s never run for office, Glen would have an immediate network thanks to her work at Goldman Sachs and at City Hall, where she spearheaded de Blasio’s housing plan. “Unfortunately everything in this town is controlled by real estate interests, and I think you have to be able to deal with them,” Abzug said.

Sharon Nelson, who worked for then-New York City Mayor David Dinkins and now runs an organization for women entering politics called Civically Re-Engaged Women, added that private sector management experience could be an asset. She likes Moskowitz, who is CEO of Success Academy Charter Schools. “(As a CEO), you have to exercise management, ideas and leadership,” Nelson told City & State. “And I think that’s really the main issue when you’re talking about doing an executive job.”

Abzug, who supported Quinn’s 2013 run, argued that the current president and CEO of Win, a nonprofit provider of homeless services, could also have a shot in 2021. Quinn has proven fundraising ability, thick skin and wide connections, Abzug said. (Another private sector manager, Jennifer Jones Austin of Federation of Protestant Welfare Agencies, has been mentioned as a possible candidate. “That’s a rumor,” she told City & State. “I operate a lot on signs, and I haven’t gotten the sign telling me that that’s what I’m going to do next.”)

In the media capital of the world, being a strong public speaker and charismatic presence on TV also matters. For these reasons, Brewer said that she likes Wiley, a New School professor and former counsel to de Blasio and former chairwoman of the New York City Civilian Complaint Review Board. “She’s fabulous,” Brewer said. “She’s on CNN a lot, so she’s got a lot of poise. She’s a brilliant attorney. When she was general counsel to the mayor, she was very knowledgeable about technology, which is my background, so I like that.”

Michael Oliva of Sykes Global Communications, whose firm works primarily with female candidates and counts Reps. Alexandria Ocasio-Cortez and Yvette Clarke among its recent clients, agreed about Wiley’s potential. “She gets a lot of earned (media) exposure,” he said.

Candidates like Wiley and Glen may suffer, though, as Quinn did in 2013, from being too closely associated with de Blasio. “We’ll see people shadowboxing the current mayor,” Gupta predicted.

Oliva is also skeptical of the chances that Quinn and Mark-Viverito have, based on their unsuccessful campaigns for mayor and public advocate, respectively. In 2013, Abzug recalled, Quinn “was viewed as more under the wing of Bloomberg,” which harmed her in that year’s Democratic primary. Abzug argued, though, that Quinn was always independent-minded and could be perceived as such if she ran this time.

Attributes viewed as assets by some are liabilities to others. To the left wing of the Democratic Party, résumés stacked with Wall Street and charter school credentials, and/or close ties to the real estate industry, are causes for concern. “In my personal opinion, any challenger who is taking money from the real estate industry is not a credible challenger in a city like New York where people are being evicted, pushed out and made homeless every day by that industry,” said Mia Pearlman, co-founder of Lefty, a new consulting firm backing 2020 candidates for state and federal office.

Morales, one of the two declared women in the race, told City & State that she will not be taking real estate money. But drawing more leftist candidates into the mayoral pipeline will require structural reforms as well, according to some activists who work on improving gender and racial diversity among elected officials.

Cat Almonte, a de Blasio alumna and managing director of The Broad Room, a new nonprofit training women and nonbinary activists, ticked off some legislative priorities. “Things like public campaign financing,” she said. “It’s hard to take at least six months with no pay (to run), ‘Medicare for All,’ student loan forgiveness – just breaking down obstacles that are preventing marginalized New Yorkers from running in the first place.”