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A look at Trump's political history with strong women ahead of debate

ARI SHAPIRO, HOST:

Former President Donald Trump prides himself on being a tough negotiator and winning arguments, but he's often flummoxed when his opponent is a powerful woman. People like Hillary Clinton, Nancy Pelosi, Nikki Haley often bring out the ugliest in Trump. He faces another powerful woman tomorrow when he debates Vice President Kamala Harris. NPR's Franco Ordoñez reports.

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UNIDENTIFIED PERSON: Ladies and gentlemen, the Republican nominee...

FRANCO ORDOÑEZ, BYLINE: In 2016, then-candidate Donald Trump infamously raged at Secretary of State Hillary Clinton, looming behind her during their second debate in St. Louis.

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HILLARY CLINTON: It's just awfully good that someone with the temperament of Donald Trump is not in charge of the law in our country.

DONALD TRUMP: Because you'd be in jail.

ORDOÑEZ: Trump described Nancy Pelosi as unhinged. He said Liz Cheney should be jailed. And he called Nikki Haley, his Republican primary opponent, bird brain.

ANDREA DUMITRU: He hates women and especially women that have strength or power.

ORDOÑEZ: Andrea Dumitru is an independent voter who lives in Charlotte, N.C., a critical battleground state. She's the kind of voter any candidate needs to win. She's voted for Democrats and Republicans in the past, and she understands Trump's appeal to many of her neighbors. But she won't be voting for Trump because, she says, he acts like a dinosaur when dealing with women in power.

DUMITRU: Because he's a toxic - the typical toxic - no offense - white old man - you know? - that just wants to control and keep control.

ORDOÑEZ: Trump built his image as an alpha male who bullies and emasculates male opponents. He takes a slightly different approach with female opponents, belittling their intelligence and criticizing their appearance.

JENNY STROMER-GALLEY: This whole topic is really tough in some ways because - how to put this - you know, Trump in some ways, is a bit of an idiosyncratic politician.

ORDOÑEZ: Jenny Stromer-Galley researches campaigns at Syracuse University. She says Trump demeans everyone, but the way he is with women who he sees as competition, like Pelosi or Clinton, takes on a different meaning because of the historic power differences between men and women. And that's what she's going to be watching for in Tuesday's debate.

STROMER-GALLEY: Will he engage in the same sort of dominating behaviors? - which, again, as a older woman who's walked through life with interesting conversations with men in positions of power over the years, you know, it sort of echoes in ways that are not pleasant.

ORDOÑEZ: The size of the divide between male and female voters will likely determine the election. In recent polling, Harris has a huge lead over Trump among women, while Trump enjoys a lead over Harris among men.

CELINDA LAKE: These are prominent, accomplished women. And if you don't respect prominent, accomplished women, then you sure as heck not going to respect me.

ORDOÑEZ: Celinda Lake, a Democratic pollster who studies women's voting behavior, says the key for Harris is winning women by more than she loses men.

LAKE: Harris needs to maximize the women's vote and generate the biggest gender gap possible, and Trump is trying to mute the gender gap.

ORDOÑEZ: Trump knows broadening his appeal with women is key. At the Republican National Convention, women like Kellyanne Conway, Trump's 2016 campaign manager and a White House senior adviser, took to the stage where she praised Trump for elevating women.

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KELLYANNE CONWAY: He saw something in me and the other working moms that perhaps we did not see in ourselves.

ORDOÑEZ: Karoline Leavitt, the Trump campaign's national press secretary now, laughed at the idea that Trump has any trouble with strong women.

KAROLINE LEAVITT: I think that's comical and false. President Trump is surrounded by strong women.

ORDOÑEZ: She pointed to the appointment of Conway, Sarah Huckabee Sanders, who is now governor of Arkansas, and...

LEAVITT: Look at who is running his campaign. The head of our entire presidential campaign is a woman, Susie Wiles.

ORDOÑEZ: Back in North Carolina, there are many women who plan to vote for Trump, like Anna Garrido.

ANNA GARRIDO: Trump is not somebody you want to go out to dinner and have, you know, a beer with, but he knows what he's doing. And the economy was a lot better, and the world was a lot better when he was in office.

ORDOÑEZ: Whether there's enough voters like Garrido to offset what's expected to be a historic gender gap for Harris is unclear. But the power of women in this election is very clear. Franco Ordoñez, NPR News, Charlotte, N.C. Transcript provided by NPR, Copyright NPR.

NPR transcripts are created on a rush deadline by an NPR contractor. This text may not be in its final form and may be updated or revised in the future. Accuracy and availability may vary. The authoritative record of NPR’s programming is the audio record.

Franco Ordoñez is a White House Correspondent for NPR's Washington Desk. Before he came to NPR in 2019, Ordoñez covered the White House for McClatchy. He has also written about diplomatic affairs, foreign policy and immigration, and has been a correspondent in Cuba, Colombia, Mexico and Haiti.