"Now it's kind of turned on her," she said. "It's not about her being 'strong and competent.' Her challenge now is 'likeability and trust.'" To McCaskill that's evidence of gender bias.
With next Tuesday's six-state round of contests, Clinton is expected to secure the number of delegates needed to clinch the Democratic nomination and become the first woman selected as the presidential candidate of a major U.S. political party. A new survey highlights the challenges she faces in the general election.
In a Quinnipiac Poll released June 1, 48 percent of women in the poll said they viewed Clinton unfavorably, but a whopping 61 percent of women said they had a "strongly'' unfavorable view of Trump and another 6 percent viewed him somewhat unfavorably. Given the negative views of Trump, 54 percent of women said they'd vote for Clinton, compared with 30 percent for Trump -- a 24 point gap. (Men back Trump over Clinton more narrowly, 51 percent to 35 percent).
Yet Clinton's overall lead in the poll is only 4 percent nationwide, within the margin of error.
This comes even after Trump has questioned her "strength'' and criticized her for "shouting.'' When the presumptive Republican nominee said last month that Clinton wouldn't get more than 5 percent of the vote if she were a man, the statement drew nods of recognition among the former secretary of state's peers who felt like they'd heard it all before.
Sen. Barbara Boxer, a California Democrat, said Clinton "really rewrote the rules and took a lot of the heat" as first lady but there remain lingering, often subtle, biases -- that women are "overly emotional, that we're not tough enough, but when we do try to be tough we're not really tough we're just shrill,'' she said.
Clinton's winding path on the issue -- from her open disdain for Tammy Wynette's notion to "Stand by Your Man" in the 1990s to unabashed doting grandma in 2016 -- speaks to changes in what voters can live with. In 1972, Edmund Muskie was essentially knocked out of the Democratic race when he was reported to shed tears while campaigning in New Hampshire. When Clinton cried in 2008 in the same state, she won the primary.
The way Clinton deals with gender -- when to deem it irrelevant, when to play it up -- has always been a central strategic question for her campaign. She largely set aside her status as a female candidate in 2008 in her losing nomination fight against Barack Obama. In the 2016 campaign, she and aides saw her new status as a grandmother as a natural opportunity to broaden her appeal and humanize her in a way her penchant for policy detail and fights with congressional Republicans over Benghazi did not.
After Trump dismissed her as playing "the woman's card," Clinton responded by saying "deal me in.'' She told CNN that she had "a lot of experience" dealing with men who act like Trump -- a knowing nod to women everywhere who've dealt with sexist comments.
The campaign declined to discuss Clinton's shift to emphasize her gender more overtly than in 2008. But the numbers show one possible motivation: if Clinton can run up even bigger gains among female voters in key electoral states, she'll go a long way toward getting to the White House.
Clinton's own personal history is almost a timeline of the national conversation on gender in politics. Some of these stories have become part of her lore, shared by her in memoirs or on the campaign trail or retold by her friends. They include:
- Her choice of Yale Law School over Harvard was made after she asked a Harvard Law professor what to do and he said Harvard already had all the women it needed.
- In 1993, when she testified before Congress as first lady and the administration's point person on its health care proposal Rep. Dick Armey, a Texas Republican, told her that "the reports of your charm are overstated."
- Comments by radio and television talk show hosts during her husband's administration and during her 2008 run for the Democratic nomination including Tucker Carlson saying whenever she appears on TV "I involuntarily cross my legs,'' and Mike Barnicle saying she looks "like everyone's first wife.''
- In her 2000 Senate campaign in New York, Republican Rick Lazio interrupted her mid-sentence during their debate and walked up close to her, wagging his finger while carrying a campaign finance pledge, an interaction that many women viewed as an assertion of male dominance.
- The 2008 campaign including a dissection of an outfit she wore during a Senate floor speech; an anti-Clinton group created by Trump confidant Roger Stone called Citizens United Not Timid, the acronym of which spells a derogatory obscenity; hecklers yelling "Iron my shirt" at a rally; and a nutcracker sold in the shape of Clinton in a pantsuit.
- As secretary of state she met with Bulgarian Prime Minister Boyko Borisov, who said he'd been warned that when she wore her hair pulled back like that it meant she was in a "bad mood." Clinton recounts the exchange in a video on her campaign website, under the headline, "Hillary Clinton accidentally intimidated a world leader -- with her hair."
Longtime Democratic strategist and former Clinton adviser Ann Lewis said that, most of the time, "My impression is that it doesn't make her angry anymore. When she quotes Eleanor Roosevelt saying a woman should have the hide of a rhinoceros, she really believes it."
What makes her struggles with some women, and particularly younger women, so surprising is that Trump seem to be doing everything in his power to drive women voters away, from his feud to Fox anchor Megyn Kelly to his statements directly and indirectly jabbing at Clinton on gender.
Clinton also is contending with challenges not tied to her gender, including her less-than-instinctive campaign skills, and populist, anti-establishment electorate. Controversies over her family's foundation, her paid speeches to Goldman Sachs and others, and her unauthorized use of private email while secretary of state also have allowed critiques of her character to fester.
"We are going through a very big psychological conversation in the United States on whether we trust women to be in executive positions," said Randi Weingarten, president of the American Federation of Teachers and a Clinton superdelegate to the Democratic National Convention. "Donald Trump has no idea what to do, not a whiff of experience, in dealing with any kind of security issues, never has had to, and yet he gets the benefit of the doubt on that, I think, because of his gender."
Cecilia Mo, a Vanderbilt University political scientist and fellow at Stanford University's Hoover Institution who made headlines with her 2008 research into gender bias in voting choice in the swing state of Florida, said there is irony in Trump suggesting Clinton is getting a break because of her gender.
"When I heard the woman-card thing, my first reaction was, it's the exact opposite -- playing the woman card actually makes it harder for women to get elected," Mo said.
She found that voters determined to be the most biased against women leaders, based on their responses a tool called an Implicit Association Test, were 12 percent more likely to vote for a man over a woman with equal qualifications.
"People were having an easier time in linking men up with leadership,'' she said.
Men, older voters, less educated voters and Republicans tended to exhibit greater hidden bias, she said, though female participants also exhibited some bias against women leaders. "It's not because of anything that is mal-intentioned," Mo said. "These things are formed by: How many role models do you see? How do my past experiences affect my current judgments?"
Kathleen Dolan, professor and chairwoman of the Department of Political Science at the University of Wisconsin in Milwaukee, said her research has led her to a different conclusion: "I believe the evidence suggests voters are generally gender-neutral."
While people do carry around "abstract gender stereotypes" such as a sense that women are better at education or men are better with national security, Dolan said voters are far more likely to replace those stereotypes with personalized views of individual candidates once they get to know them -- and are primarily likely to vote for or against a candidate based on party identification.
"Campaign professionals, when they work for women, they believe that they have to manage the sex of their candidate because they believe that voters are highly conscious of gender and that it really matters,'' Dolan said. "I and some others believe at some level the campaign professionals are just wrong."
Electoral politics has many variables -- incumbency status, records and party identification, for example -- and there isn't evidence that gender is a dominant factor, she said.
Trump showed in the mostly male Republican primary that he is an "equal opportunity abuser," Dolan said. Part of the reason voters and the media take note when he says something unkind to Clinton, she said, is that there remains a "sexist vestige that you have to be nice to the woman."