A Tale of Two Grifters: The Winding, Parallel Careers of George and Kellyanne Conway

While the Conways’ marriage has been the subject of some heated speculation, I ultimately don’t care much about the inner workings of their relationship, which was recently described by Washingtonian magazine as “the weirdest, most baffling, most fascinating, most gawked-at-and possibly perfectly healthy-marriage” in our nation’s capital. But I thought of them recently as I read article after article about Republicans who, after having attached themselves to Donald Trump like a barnacle to a big bloated whale they thought was going places, are beginning to belatedly fret that their alliance and allegiance to a man who increasingly looks like he may go down in flames. It’s a comforting thought, that people who helped facilitate Trump’s appetite for destruction may, for once, actually face some real material consequences, ones that they absolutely deserve.

Then I remember the Conways, who emerged from the rightwing muck of the ’90s and managed to supercharge their careers and reputations during the Trump era, and I once again despair. To trace how they got here can serve as an object lesson in how the worst buffoons of the past four years may, far from being exiled, find themselves thriving. For anyone who thinks that a post-Trump era will be some sort of fresh start, the unfortunate reality is that these ghouls are going to be with us for a long time.

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That the Conways met via the assistance of Ann Coulter is a sign of their immersion in the muckiest corners of the Republican swamp. As the story goes, it was the late ’90s, and Conway saw the vision that was Kellyanne on the cover of a Washington society magazine. He reached out to their mutual friend Coulter for an introduction, and they were married two years later.

Kellyanne Fitzpatrick had grown up in New Jersey in a home filled with the women of her family, her father having left the family when she was a young child. She’d become a Republican in high school after seeing a Ronald Reagan speech. After attending law school, she launched her polling company in 1995 after stints working for Republican pollsters like Frank Luntz, focusing on women’s issues and later branched out into consulting for corporate clients like Martha Stewart’s media empire. While she regularly parroted talking points to mainstream outlets on women voters and abortion, Kellyanne was no centrist—beginning in the mid-’90s, she lent her expertise to groups that were considered too out there for mainstream Republican consultants, including the far-right think tank Center for Security Policy, as well as the extreme anti-immigration group FAIR. (According to Steve Bannon, it was Kellyanne’s immigration polling that created “the intellectual infrastructure” for Trump’s victory in 2016.)

But it was clear Kellyanne had a hunger for the political spotlight, and in those days, there was no better way for a reasonably attractive conservative woman to make a splashy name for themselves than getting their face on cable news. It was the era of the “leggy blonde Republican” talking heads, dubbed “stiletto conservatives.” This group of “pundettes” was best embodied by Ann Coulter, the late Barbara Olson, and Laura Ingraham and soon enough, Kellyanne, to the point that a 1998 Harper’s Bazaar profile described Kellyanne, along with Coulter and several other rightwing women, as “Washington’s Spice Girls” and a “new breed of conservative babe.” They were the “bad girls of the radical right” who were “hellbent on ‘the destruction of every liberal program constructed in America over the past generation.’”

It was as a pundit that Kellyanne started to become the Kellyanne we know today, appearing on CNN where she was its Republican “Gen X” analyst and Fox News as well as Bill Maher’s Politically Incorrect, pushing her own brand of conservative anti-feminism and fashioning a name for herself as a rightwing warrior. Shortly after George W. Bush entered the White House, Kellyanne sounded what now reads as a preview of her time working for Trump. “I fear we have become mathematicians and not ideologues,” she told the Associated Press of the Republican Party, criticizing programs supported by Bush that she believed didn’t fire up the party’s conservative base.

As for George, he had also fallen for Reagan in high school, and went on to become the head of Yale Law School’s chapter of the Federalist Society. As Kellyanne was clawing her way upwards, George, who by then was enriching himself as a partner at a tony law firm, also began carving a place for himself in the ugliest corners of the Republican Party, working largely behind the scenes as part of what Hillary Clinton famously described as a “vast right-wing conspiracy” to use Bill Clinton’s alleged sexual impropriety to take him down.

In his 2002 memoir, David Brock described George as a “disgruntled New York lawyer” who “almost single-handedly brought down the president.” That’s perhaps an exaggeration, but George secretly advised Paula Jones, drafting her Supreme Court brief that argued her case should go forward, and connected Linda Tripp with her attorney Jim Moody, a friend and fellow member of the Federalist Society. (The two friends also reportedly delivered Tripp’s secretly recorded audio tapes of Monica Lewinsky to a gleeful Ann Coulter, a friend of Conway’s.) Conway seemed to delight in the most salacious details of Clinton’s sex life—he was the one who allegedly sent Matt Drudge the tip about Clinton’s penis, claiming that according to Paula Jones, “Clinton’s penis is curved when erect,” and that “if she is correct, then Clinton has a urological condition called Peyronie’s disease.” According to Brock’s memoir, when the two were watching TV together one day, George “leapt up from his chair triumphantly, with his fist raised above his head” when a segment featuring Clinton displayed the words “oral sex” on screen.

How fitting, then, that Kellyanne and George, both of whom clearly delighted in playing to their party’s most debased instincts and were willing to use any ammunition to advance both Republican interests and their own, met and married and then subsequently swam into Trump’s orbit.

Without Trump, Kellyanne, who became Trump’s campaign manager at the urging of the Mercer family, would likely still be a B-level D.C. power broker and not the icon to the Republican base she is today. Without Trump, George would have a fraction of his current number of Twitter followers, even less influence, and no rationale to kick off the Lincoln Project, which is nothing if not a very ingenious scam to enrich some of the worst Republicans from the previous decade, whitewash their reputations, and ensure that they’ll have enduring relevance in the coming years.

That Trump has enabled a whole orchestra section of grifters to benefit from his administration is obvious by now. That the Conways, nothing if not two people who should by all rights be bit players, were elevated by the Trump presidency and now find themselves seamlessly transitioning to a bright future as we begin to image a post-Trump age is both depressing and predictable. Kellyanne may not be in the White House anymore, but she’s not going anywhere. Lucrative book deals are reportedly being thrown her way, and can’t you see her with her own primetime spot on Fox News? George has ostensibly stepped away from the Lincoln Project, but the news that the group is planning to become its own media empire, complete with books, podcasts, movies, and TV shows, offers a hint of what George may get up to post-election.

Grifters, after all, always find their next mark.