Philly has had 99 mayors. Could we elect the first woman this year?

Philadelphia has long been a city of historical firsts, but when it comes to electing a woman to run the place, it could be one of the last.

Of its 99 mayors dating back to 1691, Philadelphia has never elected a woman. It’s joined only by New York on the list of big U.S. cities never to have a female executive. Four women are running in a crowded race this year: former Councilmembers Helen Gym, Cherelle Parker, and Maria Quiñones Sánchez, and former Controller Rebecca Rhynhart.

2023 could be the year of the woman. Some prominent female politicians argue it should be.

“It’s never happened, and then suddenly it happens,” said former U.S. Rep. Allyson Schwartz, a Democrat who represented Montgomery County and part of Philly. “You always look to the next election ... but it’s been tough in Philadelphia and given we’ve had so many women on City Council, it’s a good question. Why’s it taking so long?”

Women are an extremely important slice of the Democratic coalition and in such a Democratic city, it’s somewhat surprising, Schwartz said. The first woman to lead a big city was Bertha Knight Landes, who was elected mayor of Seattle in 1926.

In Philadelphia, not many women have run for mayor. Happy Fernandez was the first to seek a major-party nomination — in 1999.

“It is way past time that qualified women step up,” she said 24 years ago at a City Hall news conference announcing her bid.

She came in a distant fourth in a crowded Democratic primary.

» READ MORE: Philly could elect its first female mayor. We asked the four women running what that would mean to them.

Former District Attorney Lynne Abraham ran in 2015 — the first woman with elected executive leadership experience to launch a bid. But her opponents had deep-pocketed backers, and her tough-on-crime background didn’t match the leftward-leaning moment. She finished third in the Democratic primary.

Other women from both parties have also fallen short: Terry Gillen, the former head of the Redevelopment Authority, entered the race in 2015 but dropped out. Republicans nominated Daphne Goggins in 2019 and Melissa Murray Bailey in 2015 — but with the party registration disadvantage at 7-1, they entered a largely losing battle.

No Democratic woman has won her party’s nomination in the city.

“It’s very discouraging to me,” said Judee von Seldeneck, founder and chair of Diversified Search Group, a senior-level executive talent agency in Philadelphia..

Von Seldeneck worked on Fernandez’s campaign in 1999 and has since worked to elect Democratic women in the state.

“This is such a great city, and I think we pride ourselves in being so open minded and about equal opportunity for all,” she said, “but when you look at it, the facts don’t always bear that out, and this is a good example of that.”

Statewide, Pennsylvania lagged behind other states in gender representation but has recently elected more women to Congress and to the statehouse. Five of the state’s 17 U.S. House members are now women, up from zero as recently as 2018.

The state has still never had a woman as governor or U.S. senator. (Both positions have been held entirely by white men.)

And while a woman has never been the city’s mayor, Philadelphia’s political class has seen its fair share of trailblazers, especially in the legislative branch.

In 1952, after the Philadelphia Home Rule charter was adopted and established the city’s current form of governance, one woman — Constance H. Dallas — sat on Council. More than four decades later, Anna Verna became Philadelphia’s first (and only) female Council president, and she held the position for 12 years. Today, women make up nearly 40% of Council.

Other firsts have been more recent.

Quiñones Sánchez was the first Latina elected to the 17-person Council in 2007. Nearly a decade later, Gym became the first Asian American woman to sit on Council. Either would break both gender and racial barriers if elected mayor. In 2018, Rhynhart was sworn in as the city’s first female controller, and in 2019, Rochelle Bilal was the first woman elected sheriff.

» READ MORE: A wave of women have upped representation in Harrisburg

Other major cities have elected their first female mayor only recently. Last year, Karen Bass became the first woman to lead Los Angeles, and Chicago Mayor Lori Lightfoot is the first Black woman to hold the office there. With their elections, and Kate Gallego serving as mayor of Phoenix, half of the six largest U.S. cities have women at the helm.

In Boston, Michelle Wu in 2021 became the first woman elected mayor in that city, which had only ever elected white men.

The election of Wu — a progressive who bested three other women and two men — in some ways showed how Boston had evolved, said Mary Lou Akai-Ferguson, who managed Wu’s campaign.

But Akai-Ferguson said that throughout the campaign, she felt some still held on to old notions of “legitimacy,” saying the men — who were polling at the bottom and finished in the single digits — still received significant media attention.

“I know that wouldn’t have happened if they were women,” she said.

While some Philadelphians aren’t shy about saying they think it’s time a woman won, the candidates themselves have referenced — but not centered — their campaigns around their history-making potential. They have, however, made their personal stories as moms in politics part of their argument for the experience they would bring to the office.

“I haven’t heard any of them directly say, ‘It’s time for a woman,’” Schwartz said of the candidates. “I’ll say it for them: It’s time for a woman.”

Schwartz, who ran for governor in 2014, said she understands the tightrope female candidates often find themselves on — balancing running a campaign with the added weight of history and representation.

“You want to be taken seriously as who you are, and that includes being a woman,” Schwartz said. “And you know how important it is to run and see more women running — but you also have to start out by really presenting yourself for your credentials.”

Von Seldeneck, who supports Quiñones Sánchez, wrote an op-ed in the Philadelphia Citizen encouraging voters to support one of the female candidates. All four women are highly qualified, she argued, so why not pick among them?

“I think it should be raised more as an issue,” she said. “It’s time for a woman mayor. People should say it out loud.”

Von Seldeneck lamented the role that money plays in politics and the early fund-raising lead self-funders Jeff Brown and former Councilmember Allan Domb have in the race.

“At the end of the day, it gets down to raising money, which is always an extra-hard challenge for women,” she said. “That’s a huge factor.”

Some research has shown that donors give more to male candidates than similarly situated female candidates. Men also tend to give more money than women do, though that has shifted in recent years with fund-raising groups like EMILY’s List and smaller female-focused political action committees.

Former City Councilmember Blondell Reynolds Brown thinks younger voters getting involved in politics may help a woman in the race this year. She looks at how her 26-year-old daughter has become more interested in politics since progressive women like Rep. Alexandria Ocasio Cortez (D., N.Y.) entered the political stage.

Reynolds Brown also thinks traditional gatekeepers — labor unions, political parties, and donors — are more supportive of women than in the past. Still, there are always coded language and questions about qualifications that women get more often than male candidates do.

“Sexism doesn’t disappear simply because you decide you got the right stuff to get in the ring,” she said.

Three of the candidates in the race — Parker, Quiñones Sánchez, and Derek Green — worked for former Councilmember Marian Tasco. Tasco is backing Parker in the race and said she doesn’t hear too much emphasis on gender, which she thinks is a good thing.

“We’re moving, I believe, away from male or female,” Tasco said. “It’s who is the best person to run the government and the strongest and the one who could get things done and work with people and make a difference.”