It wasn’t happenstance or just casting balance that his Apprentice sidekick was a woman, nor that his daughter Ivanka had become one of his closest confidants. He felt women understood him. Or, the kind of women he liked—positive-outlook, can-do, loyal women, who also looked good—understood him. Everybody who successfully worked for him understood that there was always a subtext of his needs and personal tics that had to be scrupulously attended to; in this, he was not all that different from other highly successful figures, just more so. It would be hard to imagine someone who expected a greater awareness of and more catering to his peculiar whims, rhythms, prejudices, and often inchoate desires. He needed special—extra special—handling. Women, he explained to one friend with something like self-awareness, generally got this more precisely than men. In particular, women who self-selected themselves as tolerant of or oblivious to or amused by or steeled against his casual misogyny and constant sexual subtext—which was somehow, incongruously and often jarringly, matched with paternal regard—got this.
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Kellyanne Conway first met Donald Trump at a meeting of the condo board for the Trump International Hotel, which was directly across the street from the UN and was where, in the early 2000s, she lived with her husband and children. Conway’s husband, George, a graduate of Harvard College and Yale Law School, was a partner at the premier corporate mergers and acquisitions firm Wachtell, Lipton, Rosen & Katz. (Though Wachtell was a Democratic-leaning firm, George had played a behind-the-scenes role on the team that represented Paula Jones in her pursuit of Bill Clinton.) In its professional and domestic balance, the Conway family was organized around George’s career. Kellyanne’s career was a sidelight.
Kellyanne, who in the Trump campaign would use her working-class biography to good effect, grew up in central New Jersey, the daughter of a trucker, raised by a single mother (and, always in her narrative, her grandmother and two unmarried aunts). She went to George Washington law school and afterward interned for Reagan’s pollster, Richard Wirthlin. Then she became the assistant to Frank Luntz, a curious figure in the Republican Party, known as much for his television deals and toupee as for his polling acumen. Conway herself began to make appearances on cable TV while working for Luntz.
One virtue of the research and polling business she started in 1995 was that it could adapt to her husband’s career. But she never much rose above a midrank presence in Republican political circles, nor did she become more than the also-ran behind Ann Coulter and Laura Ingraham on cable television—which is where Trump first saw her and why he singled her out at the condo board meeting.
In a real sense, however, her advantage was not meeting Trump but being taken up by the Mercers. They recruited Conway in 2015 to work on the Cruz campaign, when Trump was still far from the conservative ideal, and then, in August 2016, inserted her into the Trump campaign.
She understood her role. “I will only ever call you Mr. Trump,” she told the candidate with perfect-pitch solemnity when he interviewed her for the job. It was a trope she would repeat in interview after interview—Conway was a catalog of learned lines—a message repeated as much for Trump as for others.
Her title was campaign manager, but that was a misnomer. Bannon was the real manager, and she was the senior pollster. But Bannon shortly replaced her in that role and she was left in what Trump saw as the vastly more important role of cable spokesperson.
Conway seemed to have a convenient On-Off toggle. In private, in the Off position, she seemed to regard Trump as a figure of exhausting exaggeration or even absurdity—or, at least, if you regarded him that way, she seemed to suggest that she might, too. She illustrated her opinion of her boss with a whole series of facial expressions: eyes rolling, mouth agape, head snapping back. But in the On position, she metamorphosed into believer, protector, defender, and handler. Conway is an antifeminist (or, actually, in a complicated ideological somersault, she sees feminists as being antifeminists), ascribing her methods and temperament to her being a wife and mother. She’s instinctive and reactive. Hence her role as the ultimate Trump defender: she verbally threw herself in front of any bullet coming his way.
Trump loved her defend-at-all-costs shtick. Conway’s appearances were on his schedule to watch live. His was often the first call she got after coming off the air. She channeled Trump: she said exactly the kind of Trump stuff that would otherwise make her put a finger-gun to her head.
After the election—Trump’s victory setting off a domestic reordering in the Conway household, and a scramble to get her husband an administration job—Trump assumed she would be his press secretary. “He and my mother,” Conway said, “because they both watch a lot of television, thought this was one of the most important jobs.” In Conway’s version, she turned Trump down or demurred. She kept proposing alternatives in which she would be the key spokesperson but would be more as well. In fact, almost everyone else was maneuvering Trump around his desire to appoint Conway.
Loyalty was Trump’s most valued attribute, and in Conway’s view her kamikaze-like media defense of the president had earned her a position of utmost primacy in the White House. But in her public persona, she had pushed the boundaries of loyalty too far; she was so hyperbolic that even Trump loyalists found her behavior extreme and were repelled. None were more put off than Jared and Ivanka, who, appalled at the shamelessness of her television appearances, extended this into a larger critique of Conway’s vulgarity. When referring to her, they were particularly partial to using the shorthand “nails,” a reference to her Cruella de Vil-length manicure treatments.
By mid-February she was already the subject of leaks—many coming from Jared and Ivanka—about how she had been sidelined. She vociferously defended herself, producing a list of television appearances still on her schedule, albeit lesser ones. But she also had a teary scene with Trump in the Oval Office, offering to resign if the president had lost faith in her. Almost invariably, when confronted with self-abnegation, Trump offered copious reassurances. “You will always have a place in my administration,” he told her. “You will be here for eight years.”
But she had indeed been sidelined, reduced to second-rate media, to being a designated emissary to right-wing groups, and left out of any meaningful decision making. This she blamed on the media, a scourge that further united her in self-pity with Donald Trump. In fact, her relationship with the president deepened as they bonded over their media wounds.
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Hope Hicks, then age twenty-six, was the campaign’s first hire. She knew the president vastly better than Conway did, and she understood that her most important media function was not to be in the media.
Hicks grew up in Greenwich, Connecticut. Her father was a PR executive who now worked for the Glover Park Group, the Democratic-leaning communications and political consulting firm; her mother was a former staffer for a democratic congressman. An indifferent student, Hicks went to Southern Methodist University and then did some modeling before getting a PR job. She first went to work for Matthew Hiltzik, who ran a small New York-based PR firm and was noted for his ability to work with high-maintenance clients, including the movie producer Harvey Weinstein (later pilloried for years of sexual harassment and abuse—accusations that Hiltzik and his staff had long helped protect him from) and the television personality Katie Couric. Hiltzik, an active Democrat who had worked for Hillary Clinton, also represented Ivanka Trump’s fashion line; Hicks started to do some work for the account and then joined Ivanka’s company full time. In 2015, Ivanka seconded her to her father’s campaign; as the campaign progressed, moving from novelty project to political factor to juggernaut, Hicks’s family increasingly, and incredulously, viewed her as rather having been taken captive. (Following the Trump victory and her move into the White House, her friends and intimates talked with great concern about what kind of therapies and recuperation she would need after her tenure was finally over.)