A Conversation With Kellyanne Conway: “I’m the Face of Trump’s Movement”

Kellyanne Conway says she’s “sorry to offend the black-stretch-pants women of America with a little color.” Conway is referring, of course, to the $3,600 red, white and blue Gucci military-style coat — meant to signify the Donald Trump revolution — that she wore, accompanied by her husband and four children, to the Jan. 20 inaugural ceremonies. The outfit instantly became an internet meme for ludicrousness, provoking a social media pile-on of insults and opprobrium personally directed at her.

“Color” also is a useful metaphor for seeing Conway, 50, as something of a bullfighter — with the news media as the bull — and her position on the Trump team as a designated target. “I’m the face of Donald Trump’s movement,” she says, with both pride and acknowledgement of her level of exposure. “Alternative facts,” the phrase she used with Chuck Todd on NBC’s Meet the Press on Jan. 22 to defend new press secretary Sean Spicer, who was trying to defend the president’s claims about the inaugural crowd (most media estimates were at about 200,000; the president’s estimate was 1.5 million), was itself a kind of over-the-top Gucci outfit, a bold, shameless, if not preposterous, take-that statement.

And while the “alternative facts” statement might seem like a catastrophic error of credibility — a few days later she was walking it back, rephrasing it as “alternative information” and “incomplete information” — it was the kind of challenge-me-if-you-can, chin-forward taunt, rendered with ladylike composure, that the new president has come to love her for. Indeed, so far, the Todd interview, part of 35 minutes of nonstop talking on three shows that Sunday morning, along with her 25-minute head-to-head with CNN’s Anderson Cooper on the infamous Russian dossier the week before — another contender for most factious and testy and give-no-quarter television segment ever — have been, she says, among the president’s favorites.

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In sum, if Donald Trump is going to war with the media — if he is to continue his war — Kellyanne Conway will be both his general and, likely, his cannon fodder. In this role, she has become an extraordinary focus of liberal rage in “the public cesspool that is Twitter,” whose users refer to her, she summarizes, as “ugly, stupid, liar, meth queen.” She is the kind of weapon that causes media heads to blow up in incredulity and frustration. Presumably, the satisfaction of seeing liberal media heads explode appeals not only to the president but also to the newly victorious Trump voter base that hates the media. (“Dear Kellyanne,” reads an email Conway received Jan. 24 and forwarded to me as an example of the multitude she says she gets, “You have more class in you’re [sic] little finger than the entire press corp. Please don’t bring yourself down to their level. Also if you ever get divorced please look me up.”)

Curiously, and perhaps as an affirmation of Trump’s media strategy, this also has made Conway quite a star, sustaining the current Trump-versus-media paradigm: Hate ’em but can’t get enough of ’em. The apoplexy she provokes ensures her constant demand. Indeed, it is this appreciation of the media’s attraction to her, and of the power that gives her, that compounds the media’s difficulty in trying to dismiss her — she holds the cards. She notes the patheticness of the recent social media campaign for a news program boycott of her as a guest: “I can put my shoes and panty hose back on and go on any show at any time.”

While she appears to be a figure of tremendously popular derision played by Kate McKinnon on NBC’s Saturday Night Live, Conway herself may have the more incisive view of the media meaning here: “Kate McKinnon clearly sees the road to the future runs through me and not Hillary,” she says. 

A few weeks ago, when Conway paid her first visit to Michael’s restaurant, the media canteen on West 55th Street in New York, the front room — always a study in power dynamics — fell into a kerfuffle. Charlie Rose, at an adjacent table, shifted his chair around to Conway’s party. Former New York politician and current socialite Andy Stein tried to invite her to an event. Washington lawyer and Obama book agent Bob Barnett lingered a bit too long at Conway’s table. Tom Rogers, former head of TiVo, hastened to recall a meeting he had with Conway more than 10 years ago (she remembered it, too). Equally, a prominent advertising executive at a nearby table, himself an adviser to Republican presidents, said, as he looked at her with intent fascination, “I can’t even look at her.”

The paradox here is that the true power behind the president is invisible — or at least carefully muted. The operative’s ultimate cachet is to be heard and not seen. In this quest or opportunity to make it into history, Conway, as much as the president might need her as a defender and want her as provocateur, understands she is sorely overexposed from her sometimes six shows before 9 a.m. and often as many after the workday. “Have I told you how sick I am of me?” she said in one of our text exchanges.

Days after the election, she turned down the position of press secretary. When the president- elect kept pressuring her to take the job, she still was having none of it. In fact, so determined has she been to be inside — “where 95 percent of what I say to him will never be public” — she turned down any job with “communications” in the title.

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Conway already occupied a unique place as the only political operative in Trump’s innermost circle — along with her, Steve Bannon, the former Breitbart chief; Jared Kushner, the real estate scion and the president’s son-in-law; and Reince Priebus, the former RNC chairman. She was a pollster who had worked in and out of Republican campaigns and administrations since, out of Trinity Washington University, she first interned for Reagan’s pollster, Dick Wirthlin. Then, too, as operative and lawyer and blonde, she had become a Republican media personality on cable television during the George W. Bush and Obama years. She and her husband, George, a partner and litigator at Wachtell Lipton Rosen & Katz, among the most well-connected and elite corporate firms, then lived in Trump World Tower, across the street from the U.N. (They now live, with their children, in Alpine, N.J.) There, she joined the condo board, whose meetings Trump invariably attended. He had seen her on television and admired her aplomb. Hence, their conversation about politics began.

Conway did some polling for Trump when he was considering a run in 2011 and came to regard him as a viable political outsider. He tried to recruit her to his campaign in the summer of 2015, but she resisted. “The rap on me would have been, ‘She’s Donald Trump’s pollster, but he doesn’t do any polling,’ ” she says. Instead, she went to work for the Ted Cruz PAC. During the disarray of the Trump campaign in August — with successive campaign managers, Corey Lewandowski then Paul Manafort, forced out — she and Bannon joined Trump. “I told him when he offered me the job, the very last thing I said to him,” says Conway, seeming to know how Trump needed to be regarded, “was I don’t consider myself to be your peer, and I will not call you by your first name. And some of the feminists may go crazy … but it’s called respect, and it’s called deference, and it’s called hierarchy.”

Working with Kushner, Conway and Bannon imposed a message discipline on the campaign: a remade economy and a disdain for liberal culture. What was to liberals an absurd construct — Donald Trump — became to others a cogent and vivid idea now wrapped into the larger-than-life Trump brand. Bannon was the scrappy author of this new message and Conway the militant defender of it.

The media yet perceived the campaign as a gang that couldn’t shoot straight — hapless, out of sync with history, in a comical losing battle over the pussy-grabbing tape, tax leaks and Russian influence, with Conway as the fantastic if not burlesque point person in each of these battles. But, seemingly beyond the media view or its grasp, the campaign was becoming a compelling show with its angry and celebratory rallies to what it characterized as the other America — not least of all by defining the media as its enemy.

While Bannon and Kushner largely stayed invisible to the world, making no appearances and giving no interviews, Conway played her part in a near-constant media battle zone. In this, she became the personification of the campaign’s defiance of the truth and its as-though-otherworldly ability to sidestep it. Every Conway appearance seemed to end with cable and network anchors in something of a near howl of liberal existential breakdown. Stoking the fury of the media, she seemed to have a skin so thick, or, more strangely, a sense of the Trump mission so strong (even though, as a Cruz partisan, she once had neatly dismissed Trump), and a contempt for the media so natural, that virtually nothing ruffled her. Whatever wounds she might have secretly nursed were soothed by the fact that she was “taking many other people’s TV time,” presumably, most of all, that of the Trump enemies. (She notes curiously how many of her media antagonists are, in private, solicitous: “The Huffington Post constantly slams me, but Howard Fineman [HuffPo‘s lead political reporter] calls to check on how I’m doing figuring out Washington schools.”)

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But in politics, Conway is aware that a president might not necessarily want confidences of the deepest kind in the hands of someone living constantly on the very edge of public disclosure (with its proximity to public humiliation). The closer you are to the person you represent, the more that puts him or her at risk. The ultimate insider is seldom the consummate outsider. (This contradiction helped scuttle both Rudy Giuliani and Chris Christie’s roles in the Trump administration.)

Hence, with the title “counselor to the president,” Conway says she is trying to dramatically scale back her life in the media, to come in, as it were, from the heat and to nurture her role as one of a handful of people closest to the president. It’s a role she defines as “having walk-in privileges.” It’s to be in on every decision, to advise on all issues. “To be in the room [where it happens],” she says. “Quoting Hamilton,” she adds. In the first week of the new administration’s operation — after she, Bannon, Kushner and Priebus all were sworn in together — she has been in on virtually all of the president’s significant meetings. That’s what’s at stake for her. To be the most powerful woman in the United States government ever.

Except that events dictate White House careers. And, almost with some reluctance, she admits she has “promised the president my role would include communications, in that I will oversee and be a part of the communications and message for the White House.”

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In other words, at any moment, her ideal inside role might go back to being her contentious outside role. Indeed, as cosseted as her new title sounds, her outside role may never stop. On the second day of the new administration, she seemed permanently stationed before the camera tents in front of the West Wing. In addition to her “alternative facts” explanation of the phantom inaugural crowds, she delivered what the media took to be an ultimate, if not last, insult by saying nope, in fact, no Trump tax returns, ever. (She says she did no such thing and merely restated that the president continues to be under audit. But in a Jan. 22 interview on ABC’s This Week, Conway said: “The White House response is that he’s not going to release his tax returns. We litigated this all through the election. People didn’t care.”)

Says Conway, “I am just trying to stand up to the cacophony, sameness and myopia of the media world.” And to imperturbably face down its incredulity, disbelief and self-righteousness.

Hers is an artful technique and a consummate piece of showmanship, of staying out of the corner of either/or (with anchor after anchor demanding of her, “This isn’t true, is it?”), of recasting any attack as ad hominem, of shifting the question to what she can easily defend and of making the media reality seem petty and gotcha. Hence, during a confrontation about the nature of presidential behavior, she blew media heads apart by suggesting that, because Donald Trump had been elected president, however he behaved was presidential behavior — which was, in fact, in some bottom-line fashion and literal definition of democracy, indisputably true. In defending, or actually being careful not to defend the particulars of the president’s view of his inaugural audience, she also was saying we all know the man has a penchant for exaggeration — hence, so what? What you see is what got elected.

In a sense, the political issue of Donald Trump’s myriad misstatements is transformed into the sport of how Conway will defend them or reduce them to merely the media’s — the loser media’s — predictable and sour grievances. It is not just Trump that the media does not know how to cover but Conway.

Conway, like the president, will be a commuter, leaving her family in New Jersey and returning from Washington on weekends. By the next school year, she hopes to move her family to D.C. Indeed, she rather hopes her husband will join her in government, perhaps at the Justice Department. (“Four private-school tuitions on two government salaries. I can hardly wait.”) She sketches out a normal, normalized Trump White House. In this ideal world, she spends her day whispering in the president’s ear and only is on television on important occasions.

Except if this world isn’t normal, if it’s the media leading a new kind of civil war or the Trump team provoking one, then Kellyanne Conway is destined to be less Trump’s quiet confidant than his relentless weapon: “If you see me on TV, it’s because he wants me there.”

A version of this story first appeared in the Feb. 3 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.