Home/Articles/The Three Acts of Kellyanne Conway

The Three Acts of Kellyanne Conway

The president’s senior counselor has left the White House. In the Trump era, her story of familial fissure is all too familiar.

In better days: Donald Trump and Kellyanne Conway on Election Night 2016 (Photo by Mark Wilson/Getty Images)

It’s late summer and Donald Trump is losing. 

The Democratic nominee is up in any poll that doesn’t strain credulity: sixteen points in Virginia (in memory a Republican bastion), fourteen in Colorado (ditto), nine in North Carolina and five in Florida. The general election polls aren’t much prettier. After stillborn hope of a major, convention bounce, evidence is illusive. It seems all that remains is gathering disaster. 

It’s against this (familiar?) backdrop, that Trump, nothing if not wily, makes a change. It’s August 2016 and Trump has ousted campaign manager Paul Manafort.

In July of that year, Manafort (once considered a steady hand) — along with the president’s up-and-comer son-in-law, Jared Kushner — had hemmed Trump in on key decisions. The selection of Trump’s running mate was the most notable example. Though maintaining a managerial public veneer, Manafort, of course, went to spectacular lengths to make a safe choice happen: He fibbed about mechanical problems on their plane back to give Trump more time with the Indiana governor, Mike Pence. But this was hidden from the public scene. It worked, and Pence got the nod, sparing the Trump ticket from a familial rival to Kushner (Chris Christie), as well as an oddball hail mary (Newt Gingrich). But by August it was clear that playing it safe was playing to lose. And with details spilling out in the New York Times of a secret ledger in Ukraine that detailed cash payments to the campaign chief of a major U.S. presidential nominee, it was no longer clear Manafort was safe at all.

Into the breach step two surprises. At the behest of the secretive, conservative Mercer family, Trump hires Stephen K. Bannon, the Breitbart chief, and Kellyanne Conway, a career Republican operative who worked stridently for Trump’s fiercest primary rival, Ted Cruz. Bannon would become nationally notorious, but on hire day, it was Conway who was already famous. 

In the nineties, Conway had been part of a group of rising stars in national politics. In phrasing that would perhaps not so readily be employed today, they were called “the pundettes.” Virulently anti-Clinton, they had law degrees and perfectly maintained blonde hair. Conspicuously, all were educated in the Northeast, auguring a GOP future shorn of a yokel image. The subtext: they had as much as sex appeal as politically savvy. They were smart. Ann Coulter. Laura Ingraham. Barbara Bracher. Kellyanne Fitzpatrick. Any center-right male in Washington so inclined plotted a way to date into the group. They were feted on Bill Maher, then running a show that also doubtless would have not survived the current year: Politically Incorrect.

Two paired off, marrying power Republican litigators— Fitzpatrick to George Conway, who had worked for Clinton accuser Paula Jones, and Bracher to Theodore Olsen, whose client won in Bush v. Gore. Barbara Olsen would die on September 11, 2001, when her plane (she was flying to tape Maher’s show in Los Angeles) would crash into the Pentagon. In marriage, Conway had cut a perhaps more anonymous figure than Coulter and Ingraham, who became elaborate celebrities in the new century. She gave birth and raised four children. Though still working and a frequent presence on the cable circuit, it wasn’t until 2016 that Conway took back center stage. 

Though Bannon would later earn a reputation for eagerness with the press, during the 2016 campaign, he stayed mostly behind closed doors, orchestrating what would become Trump’s shock victory in the Midwest. Before election night, it had been Conway who was front-and-center, the borderline face of the franchise — other than the candidate himself. “When Donald Trump spoke in Chester Township, Pennsylvania, outside Philadelphia, he wasn’t the only star at the event,” Ryan Lizza reported in the New Yorkerat the time. “Kellyanne Conway, his new campaign manager, who grew up nearby, and who has become ubiquitous on television, was greeted as a celebrity. ‘Did you see the people asking me to sign their posters and hats?’”

But with recognition came notoriety. Her star again faded, setting up the veteran Washingtonian for an at-times depressing, long crescendo in the public eye. Kate McKinnon, the breakout Saturday Night Live star of that year, paired her portrayal of Democratic nominee Hillary Clinton with a basically unsparing representation of Conway as a vapid press hound. By winter, during the transition and new administration (where along with Kushner, Trump’s daughter Ivanka and former Jeff Sessions aide Stephen Miller, Conway was named senior counselor), Conway’s stock in Washington had fallen, fair or not. “I will say: Kellyanne Conway does not need to text our show, just as long as I’m on it, because it’s not happening here,” Morning Joe host Mike Brzezinski said in February 2017. “She’s just saying things just to get in front of a TV set and prove her relevance because behind the scenes, she’s not in these meetings. She’s not credible anymore.”

It was an outside impression — that she was uninvolved in crafting policy — which likely prolonged her tenure in the White House, but perversely, extended and expanded her personal agony. Aides to Trump who got too famous for their internal influence — Bannon, and the former generals John Kelly and Jim Mattis — were all discarded before the administration even reached its third year. That sword, political survival, cuts both ways, however, as soon enough Conway’s own family would be involved in cutting her down. McKinnon “has me down!” Conway (trying to laugh it) said on Twitter in 2016, when the portrayal debuted. “We got a good laugh in our crazy house.” Unnoticed at the time, that “crazy house” that would become infamous.

After flirtations with serving as Trump’s solicitor general, among other posts, George Conway soured considerably on the administration. After the Republicans relinquished the House of Representatives in 2018, Conway’s husband let loose, telling Yahoo! News that Trump’s rule was a “sh*tshow in a dumpster fire.” His Twitter feed, refreshed with daily invective against his wife’s very public employer, became a sensation in “NeverTrump” world, and inside the liberal press. He founded the Lincoln Project, a collection of neoconservatives and anti-Trump Republicans attempting to hound Trump out of office through ad buys and social media.

A dyspeptic marriage on display for all to see may have been good fun for some, but what came next was most certainly not. “You know life isn’t fair when you wake up to your own mother speaking aside a homophobe and a rapist,” Claudia Conway, the couple’s teenage daughter, tweeted in August, referring to Mike Pence and Donald Trump. “Let me intern for you,” she tweeted at Alexandria Ocasio-Cortez. Unfortunately though, as it can be with teenagers (or many users of social media), it seemed there was no line the younger Conway would not cross. My mother’s job ruined my life to begin with,” she tweeted. “Heartbreaking that she continues to go down that path after years of watching her children suffer. Selfish. It’s all about money and fame, ladies and gentlemen.”

Her father was not spared. “As for my dad, politically, we agree on absolutely nothing. We just both happen to have common sense when it comes to our current president. Stop ‘stanning’ him,” Claudia Conway tweeted. “How do I get in touch with pro bono lawyers,” Conway continued to tweet. “I’m officially pushing for emancipation.” She said: “I’m [devastated] that my mother is actually speaking at the RNC. Like DEVASTATED beyond compare.” She alleged long-standing abuse. After the Republican National Convention, Kellyanne Conway announced she was leaving the White House. She was joined in a resignation by George Conway, who said he left the Lincoln Project, and became far less prolific on Twitter (though he continues to retweet anti-Trump accounts such as Jennifer Rubin and Anthony Scaramucci at a feverish clip).

Conway has granted a Fox interview since leaving government, saying “undercover” Trump voters will “surprise” on election day. The clip was wildly mocked (though, given the 2016 experience, if Conway knows anything, she probably knows a little about that). And MSNBC host Chris Hayes piled on her legacy this week, playing a clip of Conway saying in the Oval Office in March that COVID-19 was “contained.” This was as news broke from Bob Woodward on Wednesday that Trump wanted to “play down” the virus to avoid a panic. “That moment, by the way, should be what everyone remembers about Kellyanne Conway,” Hayes said. “Maybe the only thing they remember about her contribution to public life.”

I don’t think I agree with Hayes. Politics has become bloodsport in American life, sparing not even the sanctum of the family. It’s the story of the Trump era— lost friends, boyfriends and girlfriends, and family members, all over politics. As the country gears up for the most vicious election in generations, and its aftermath, we could do worse than applaud the Conways for trying, in some way, to save their “crazy house.” 

about the author

Curt Mills is Senior Reporter at TAC covering national security, the 2020 campaign and the Trump presidency. Previously, he reported for The National Interest, Washington Examiner, U.S. News & World Report and the Spectator. Mills was a 2018-2019 Robert Novak Journalism Fellow and is a native and resident of Washington, D.C.

leave a comment

Latest Articles