Could a woman beat Trump? Democrats worry – and hope.

Emerging from a Londonderry rally for Sen. Kamala Harris, Holly walks to her car with her head low, weaving through the double-parked cars. A “Kamala for the People” sign hangs limply from one hand.

“I absolutely love her,” says Holly in a fretful tone that doesn’t match her words. “But I don’t know. I’m worried about it.”

A recent swing through New Hampshire rallies turned up a number of Democrats who share Holly’s unease: that a woman might not be the best choice to beat President Donald Trump.

“I think we’re long overdue for a woman president,” says Edna Gabriel, from Revere, Massachusetts, following an event for former Vice President Joe Biden in Laconia, New Hampshire. “But having a woman against Trump, it frightens me.”

“It was my first choice to vote for a woman for president,” adds Susan Walsh, from Norwell, Massachusetts. But “I just see [Mr. Trump] lumbering over [Sen. Elizabeth] Warren during the debate.”

In many ways, the race for the 2020 Democratic presidential nomination has been a breakthrough for women candidates. More have entered the contest, and emerged as serious contenders, than ever before.

At the same time, there is palpable anxiety among Democrats that in the age of Trump, nominating a woman might be too risky. Many voters say they would support – or even prefer – a female Democratic presidential nominee, but they fear other Americans won’t.

Some of this stems from the party’s shellshocked reaction to Hillary Clinton’s loss in 2016. Some of it is based on polling that shows Mr. Biden and Sen. Bernie Sanders leading President Trump by wider margins than do Senator Harris and Senator Warren.

Ultimately, it reflects the fact that many Democrats are determined to defeat Mr. Trump – and thus are putting electability at the top of their list of desirable nominee qualities. With the 2020 election expected to come down again to a handful of Rust Belt states with a preponderance of less-educated white voters, many urban and educated Democrats find themselves going through mental gymnastics to try to imagine what swing state voters want.

But would a woman really be less electable? It’s important to remember that this assumption could become a self-fulfilling prophecy, says Jennifer Lawless, an expert on gender and politics and a professor at the University of Virginia. True, some voters may judge a candidate based on her gender, but presidential elections and voters’ reactions to candidates are actually far more nuanced than that.

“A woman who was a die-hard Clinton supporter and now likes Warren, she says, ‘I’m not going to do this again. I’m going to support Biden because there’s no way we can win Wisconsin, Michigan, and Pennsylvania [with a woman],’” she says. “In this case, we are assuming the American people are less evolved than we are.”  

Who’s electable?

“Electability” is a word Democratic voters have prioritized for 2020 candidates in multiple polls. But the candidates who have won before heavily influence whom these voters see as electable. Essentially, that means white men.

In a recent USA Today/Ipsos poll, half of Democrats said a woman would have a harder time than a man running against President Trump in 2020. And while 90% of Democratic respondents said they’d be comfortable with a female president, only 44% said their neighbors would accept a woman in the Oval Office.

“People keep being told, by candidates, pundits, the media, that the electability of women is a problem,” says Christina Reynolds, vice president of communications at Emily’s List, a political action committee to elect Democratic women in favor of abortion rights. “I think it’s a flawed assumption. We are incredibly bad as a society at predicting electability.”

But here’s the problem: The best way to look electable is to get elected, say experts. If Senator Warren wins New Hampshire, where a recent CBS poll has her inching ahead of Mr. Biden, and other early primary states, voters’ sexism fear may fade. But it likely won’t be totally dissolved until a woman wins the presidency.

Look at the past two presidents for example, says Ms. Reynolds. In 2008 the United States questioned the electability of a black man, and in 2016 the country questioned the electability of a reality TV star. This year there seems to have been no question of Sen. Cory Booker’s electability as a black man, and many Democrats were hopeful that the celebrity Oprah Winfrey would announce a bid. 

When speaking to reporters Saturday in Manchester, New Hampshire, Senator Harris said the 2020 presidential race isn’t the first time she’s been confronted with questions about gender and electability. In both of her previous positions, as district attorney of San Francisco and attorney general of California, she made firsts on the basis of gender and race. 

“I think that there is sometimes a difficulty, and maybe even an inability, for folks to imagine what they’ve not seen before,” says Senator Harris. “It doesn’t mean it’s not possible.” 

And as female Democratic voters across New Hampshire were quick to point out, Mrs. Clinton actually won the popular vote by almost 3 million votes. The former secretary of state lost the Electoral College because of voter turnout in specific geographic pockets of the U.S., a frustration that leads many New Hampshire Democrats to call out regional differences. 

“I forget that everybody doesn’t think like we do,” says Ms. Gabriel from the line to enter Mr. Biden’s rally in Laconia. “We’re used to supporting strong women up here.” 

“In New England we have one mindset and that is different from people down South,” says Claire, who declined to give her last name, while sitting in her sky-blue minivan in a Hannaford’s parking lot in Rochester, New Hampshire. “I think down there people just trust men more, I mean you don’t see a lot of females getting elected down there.” 

Actually, women’s success in politics isn’t geographically constrained, says Ms. Reynolds. If 2016 proved the majority of the country would vote for a woman, then 2018 proved that women could win important races – races in states that lost Mrs. Clinton the Electoral College. Last year Michigan elected a record number of women, including to the U.S. Senate and the top three state offices. Wisconsin reelected Sen. Tammy Baldwin despite a flood of funding to defeat her. Pennsylvania went from having zero women in Congress to four – the largest class of women the state has ever elected. The 10 states with the most women in the state legislature are scattered across the country, and the top three are Nevada, Colorado, and Oregon, according to Rutgers University’s Center for American Women and Politics. Women governors reside across the country, including “down there” in Alabama.

“You look at these states, and you see that women win all over the place,” says Ms. Reynolds. “There is certainly sexism in politics, there is sexism in our society, but I also think there [are] a heck of a lot of very engaged women right now who are interested in change in politics.”

Trump’s Achilles’ heel

Derry Town Councilor Joshua Bourdon tells a story about his daughter Sasha when introducing Senator Harris at her Londonderry rally, held at Mack’s Apples.

“I was putting her to bed and she said, ‘Daddy, why can’t a woman be president? Hillary lost and she was great,’” says Mr. Bourdon. Senator Harris nods knowingly. Audience members collectively sighed. 

Several mothers and their daughters came to Mack’s Apples to see Senator Harris, such as Carol Linstid from Amherst, New Hampshire, and her daughter Caitlin. Ms. Linstid watches Senator Harris walk across a stage surrounded by bales of hay and baskets of waxy apples, talking about gun reform and children’s safety. Another mother holds her baby in a “Future Voter” onesie. Two female Londonderry High School students have come, even though they will still be too young to vote in 2020, because it would be “cool” if a woman – this woman – becomes president. 

Pundits and political experts point this out as a benefit: It will excite these women and bring them to the polls. But several New Hampshire voters have a different logic for putting up a female nominee: A woman is best equipped to beat President Trump. 

“Women are Trump’s Achilles’ heel,” says Catherine Johnson, who traveled to Senator Harris’ rally from Hanover, New Hampshire. “He doesn’t know how to deal with strong women.” 

Kathy Hempel and Jennifer Martelli, two friends in mint green “Warren for NH” T-shirts who traveled from Marblehead, Massachusetts, to support Senator Warren at the New Hampshire Democratic Convention the day following the Harris rally, agree with Ms. Johnson. Just look at how Senator Warren defeated incumbent Massachusetts Sen. Scott Brown in 2012, says Ms. Martelli.

“We can’t say, ‘We’re afraid so we’re not going to run the best candidate,’” says Ms. Martelli.

“I mean, no one thought that Trump would win,” adds Ms. Hempel.

But, but, but ... the worry persists. Mrs. Clinton seemed a sure thing. She was going to win, break the glass ceiling, and keep Democrats in the White House. The sheer surprise of her loss continues to haunt her female supporters.

“Women in my age group have great doubts,” says Claire. “I mean, just look historically.”

But did Mrs. Clinton lose because she was a woman, or did she lose because she was tied to her husband’s two terms and all their drama, and battered by Republican attacks on her probity while the press heavily covered the FBI investigation into her emails?

“There is no clear evidence that sexism cost Hillary Clinton the election,” says Ms. Lawless. “Hillary’s problems were more the fact that she had the last name ‘Clinton,’ not the fact that she lacked a Y chromosome.”