Friends have watched the Conway drama like a slow-moving train wreck, sometimes too timid to really ask what’s going on. As of late February, the Conways are still together, joined by 20 years of marriage and four children. Still, conversations with numerous sources from both camps—yes, there are camps with the Conways—reveal the couple to be in an extremely fragile state—miles away from “closure.” The wounds are still raw from their public clashes. As important, they don’t have a mutual grasp on what has just happened to the country, creating a high level of exasperation. George believes that Trumpism should be eradicated from the planet. Kellyanne, on the other hand, is still in explain-away-daddy mode, not giving an inch. In a statement condemning the Capitol riot, she not only failed to acknowledge the role of Trump’s rhetoric, but also praised his leadership. Given every opportunity to amend or clarify that statement for this piece, she declines.
How did two extremely smart people allow the presidency of one of the world’s most corrupt men to wreak such havoc on their family, never mind the country? In the last four years, both George and Kellyanne leaned into different sides of a certain upright conservatism. George is a man who adheres to a certain rule-following propriety—which would suggest he might have held his tongue while his wife was in the White House. But there’s another facet to George that overrides everything else. “George has a deep commitment to what he feels is right,” says his former Wachtell colleague David Lat, a legal writer. “His commitment to doing and saying what’s right, combined with an enjoyment of fame, have overcome the propriety-focused aspect of him.” As for Kellyanne, she’s a paragon of loyalty, says Luntz, the kind “that you don’t find in Washington anymore.” But in the opinion of many, that loyalty crossed the line to drinking the Kool-Aid.
“She fell into the cult,” says Michael Cohen, Trump’s ex-lawyer, who understands better than most the thrall of Trump. “The biggest mistake that people make, Kellyanne included, is they start to believe that they are relevant,” says Cohen. “And they begin to try to assume Trump’s arrogance.” Indeed, she came to embody many Trumpian passions: winning, or talking about winning, a lot; shaming the naysayers; and never being wrong. Kellyanne did not push the “Stop the Steal” narrative that incited the riot; a month after the election, she finally acknowledged that Joe Biden won. Yet her ease at subverting the truth during her tenure at the White House, her unshakeable righteousness, helped ease the way for the Big Lie.
The primary season of the 2016 election had been simpler times for Kellyanne and George. As is well known, they were working hand in hand. George was supporting Ted Cruz, and Kellyanne was running a super PAC for the Texas senator, whose wife Trump had insulted and whose father, Trump insinuated, was in on the assassination of President Kennedy. Kellyanne went after Trump, calling him the “thrice-married, non-churchgoing billionaire” who “says he’s for the little guy but actually built a lot of his businesses on the backs of the little guy.” He was, according to Kellyanne, “unpresidential,” “vulgar,” and offensive to women.
By the summer of 2016, Trump was the Republican nominee, but hurting for female voters and in need of a campaign manager. On the advice of Robert and Rebekah Mercer, the Cambridge Analytica and Breitbart billionaires who’d shifted their support from Cruz to Trump, he asked Kellyanne to become his campaign manager. But he wanted her on the cheap, because he’s Trump.
Kellyanne was in. The clout that would come with being the first female to win a presidential campaign outweighed any remunerative concern. Trump got a great deal. Those pesky disavowals of Trump she’d made? She’d blow them away like feathers. She had a whole bag of tricks at the ready. First there was the double-dealing. As a regular guest on Morning Joe, she praised Trump as “masterful,” and then, on one occasion, according to cohost Mika Brzezinski, took off her microphone and said, “Blech, I need to take a shower.” Morning Joe banned Kellyanne shortly thereafter. And then there was her bold gaslighting—like her claim that “it was Donald Trump who put the issue [of Barack Obama’s birth certificate] to rest” and her insistence that he “doesn’t hurl personal insults.” If the smiling blonde lady on television was saying it, it had to be true, right?
Veteran Republican strategist Rick Tyler, who’d been Cruz’s communications director, watched with amazement. “As a spokesperson, you can omit things, you can highlight certain things, you can reframe the conversation,” he says. “But when you say things that are flat-out wrong, that’s where I draw the line. I’m not going to debase myself, because there’s life after this client.” But Kellyanne had her champions—like Chris Christie, who over the course of their 18-year friendship bonded with her over their tough Italian mothers. He did debate prep with her in both 2016 and 2020 and sees her as a messaging wizard.
“There’s very few people in political life who know how to use language as effectively as Kellyanne and are more effective in communicating to President Trump,” says Christie. He says that when Trump was promising to refuse defeat in 2016, she told him to go softer. Christie adds, “She’s not present in 2020. And I think her absence is very, very loud in this postelection period.” He credits her for putting the opioid issue in front of President Trump, which resulted in the bipartisan passage of the SUPPORT Act.
Back in 2016, George was still very much in his wife’s corner. In the binary choice between Hillary Clinton and Trump, he cautiously supported Trump. As a member of the Federalist Society, he prioritized getting conservatives on the Supreme Court. For all of Trump’s obvious flaws, George then believed that “[Trump] will realize that the office is something much bigger than him,” as he later told fellow Lincoln Project cofounder Ron Steslow on a podcast, “and there were going to be these people around him who will constrain him.” People, perhaps, like his wife, whom he clearly doted on. On election night George wept with pride for what she had achieved, and screamed, “She did it! She did it!” On inauguration night he stood aside and held her fur coat, while Kellyanne posed in a red gown, beaming for cameras. George got a bit swept up too. He threw his hat in the ring for the job of solicitor general. After that job went to someone else, Attorney General Jeff Sessions asked if he’d be interested in the job of assistant attorney general in the civil division at the U.S. Department of Justice. Again, George agreed to be considered. He had spent decades working in the private sector and was ready to serve his country.
Kellyanne, the winning campaign manager, was slipping into the position of the president’s “counselor.” As she liked to point out, this meant she had walk-in privileges in the Oval Office. But television was his favorite forum. As Trump watched the shows, Kellyanne pioneered new ways to dodge the truth—or run a truck over it—for his pleasure. When NBC’s Chuck Todd took her to task on the assertion that the president’s inauguration crowd size was the biggest in history, she famously retorted that she had “alternative facts,” and a defining catchphrase was born. To defend Trump’s policies, she could go to bizarre places. When Trump tried to push the Muslim ban, she talked about “the Bowling Green massacre,” an ostensible massacre in Kentucky carried out by Muslims. She later claimed it was a slip of the tongue, even though she cited it in three different outlets.