Years later, George would marry Kellyanne Fitzpatrick, a publicity-prone Beltway pollster, and move with her to an apartment in Manhattan’s Trump World Tower. There, he caught the future president’s attention by arguing to the condo board against stripping Trump’s name from the exterior. The speech earned him an appreciative call from the mogul and an offer to join the board. He declined, but Kellyanne said she’d do it.
“My laziness led her to meet Donald Trump,” he said in a recent interview.
Kellyanne would go on to become Trump’s campaign manager in the crucial final months of the race and one of his top White House aides. And now President Trump, according to sources who would know, has asked George to run the Justice Department’s civil division. Pending Senate approval, he would become one of the administration’s top lawyers, tasked with guarding the president and his policies from legal challenges.
It’s a big job. Already, Trump has had two major executive orders — one potentially cutting off federal funding from sanctuary cities, another banning entry to the United States from predominantly Muslim countries — blocked by the courts. Then there are the investigations into his ties to Russia and the turmoil surrounding his decision to fire FBI Director James B. Comey. Not since the Clinton administration has the term “impeachment” been bandied about so much.
Back then, George helped sow the chaos.
Now, he’s coming to Washington to try to put things back together.
There is no photo of George Conway in his high school yearbook. His name is listed near the end, under a section marked "Camera Shy."
Thirty-seven years after graduating from Marlborough High School in Massachusetts, it’s still a fitting description for a man who likes to operate behind the scenes. The son of an organic chemist from the Philippines and a defense contractor for Raytheon, Conway was a whip-smart kid who graduated from Harvard at 20 and presided over the conservative Federalist Society at Yale Law.
He took a job at the prestigious New York firm of Wachtell, Lipton, Rosen & Katz, earning a spot as a million-dollar-a-year partner by his mid-thirties. That’s when he was approached by lawyers representing Paula Jones — a former Arkansas state employee who was suing President Clinton for sexual harassment.
No fan of Bill Clinton, George leapt at the opportunity to work against him — but insisted he do so in secret, as his heavily Democratic firm (Bernard Nussbaum, Bill Clinton’s first White House counsel, was a partner) would probably not approve.
His unpaid work — research, legal briefs and organizing moot courts for the team to practice their arguments — had him working alongside fellow GOP lawyers Ann Coulter, the future arch-conservative pundit, and Jerome Marcus, a veteran of Ronald Reagan's State Department. Coulter offered a nickname for their clique of off-the-books workers: "the Elves." And they had a mischievous side. When it appeared as though Bill Clinton and Jones might settle out of court, Conway and Coulter were determined to prevent that. "It was contrary to our purpose of bringing down the president," she later told the journalist Michael Isikoff, as reported in his book "Uncovering Clinton."
So to keep the story alive, they started leaking.
“The distinguishing physical characteristic that Paula Jones says she believes she saw is that Clinton’s penis is curved when erect,” George wrote in an email to Matt Drudge, according to “The Hunting of the President,” by Gene Lyons and Joe Conason. “If she is correct, then Clinton has a urological condition called Peyronie’s disease.”
Several critics argue this was a violation of the gag order, though Conway denies it, noting that he was not technically the attorney on the case nor privy to protected details. It was also never corroborated. But according to Coulter, that was never the point. It would “humiliate the president,” Coulter told Isikoff — and keep him from settling, she reasoned.
George says now he has no recollection of sending emails to Drudge and denies he was “out to get” the president.
“The notion that it was some sort of long-term conspiracy to destroy Bill Clinton is ludicrous,” he said. “It was mystifying to me that they never settled.”
But they didn’t. And as the case proceeded, the president’s sexual escapades became public record, and Monica Lewinsky became a household name.
“If you told me in 1994 that this would lead to the impeachment of the president, I would have said you are a certifiable lunatic,” he said. “It was just a civil case. It was popgun. It was nothing, and nobody took it seriously.”
Throughout the 1990s, George stayed on the case, but he remained under the radar. He helped set up Lewinsky confidante Linda Tripp with a lawyer when she decided to bring her information forward, according to a New York Times report in 1999. When Tripp's pal Lucianne Goldberg, a literary agent and conservative gadfly, wanted that story to go public, she says Conway helped get her "bombshell" to Drudge. He denies these accounts.
"George is somebody who likes to be in the mix, where the action is," said David Lat, the founder of the blog AboveTheLaw.com and friend of Conway's from his days working at Wachtell. "He is willing to upset convention or do things that might be unexpected."
On this, George agrees.
“I have contrarian tendencies,” he said.
He grew up near Boston but became a Yankees fan. His mother handed out leaflets for George McGovern, but he fell for Reagan after reading Milton Friedman in high school.
But for all his political enthusiasms, he never let them take over his life. He’s worked at the same law firm for almost 30 years, focused on the needs of tobacco companies and other corporations.
“It’s not so much about red or blue there, but about green,” said Lat.
Lat, who considers himself a political centrist, is one of many who will cross the aisle to praise George as funny, generous and brilliant.
“He is an absolute joy to be around,” said Lisa Blatt, a D.C. lawyer who used to work with George and just happens to be a supporter of President Barack Obama and Hillary Clinton.
“George was already an outspoken conservative when I met him in law school,” said David Wecht, a Democrat and associate justice of the Supreme Court of Pennsylvania. “But he was always willing to debate, always receptive to other arguments. My most delightful exchanges in law school were probably debating him at Federalist Society meetings.”
He had friends everywhere, but it took time for George — pudgy, soft-spoken and borderline shy — to find love. Not that he didn’t have a type. He became friends with Laura Ingraham, often inviting her to the ski slopes or the beach. And while nothing ever happened between him and Coulter, she was responsible for him meeting the other blond Republican It Girl, who would become his wife.
He was familiar with Kellyanne from her television punditry spots. But inspiration struck one day in the late 1990s when he spotted her on the cover of a society magazine. He called Coulter and asked for an introduction.
He courted her with trips to his Hamptons beach rental and tickets to baseball playoffs. And at some point, Kellyanne remembers telling a friend: “I find that his near-constant presence doesn’t annoy me.”
Their wedding, at the Cathedral Basilica of Saints Peter and Paul in Philadelphia, was a decadent affair. The cake was so big it had to be cut into pieces to fit in the door.
“It was the biggest, fanciest wedding I’ve ever been to in my entire life,” Goldberg recalled. “All seven of the members of the right-wing conspiracy were there. The rest were just Republicans.”
The years that followed were relatively quiet, as they raised four children and made a lot of money. Kellyanne's polling work (she commuted between Washington and New York) and occasional TV appearances made her famous for Washington, but nothing like what would happen after Trump came calling.
“I remember going on Google after she was announced as campaign manager,” said George, “and seeing her name was the most-searched term in the country. I knew right then our lives would never be quite the same.”
He turned to security consultants to keep her and the family safe. They watched the "Saturday Night Live" impersonations for a while — they all found "Kellyanne's Day Off" to be "hysterical" — but pretty much stopped watching when it started to seem mean. He took on the role of "Mr. Mom," watching over the kids more with his wife gone so often. And he regrets nothing.
“I couldn’t have done this without him,” Kellyanne said.
George spent election night nervously watching returns with his wife’s team at the Midtown Manhattan Hilton. When the networks called it for Trump, he couldn’t hold back his pride. Tears streamed down his face, and he shouted to anyone who would listen: “She did it! She did it! She made history.”
Said Kellyanne: “He’s always been the more emotional one.”
Now it’s George’s turn to move to Washington. There has been no official nomination announcement, but the Conways hope to close this month on an $8 million home in the District; George and the kids will move down when the school year ends.
Conway’s appeal to the president seems clear: not only one of the best civil litigators in the country, but also a man who’s fought to keep the Trump name emblazoned on the skyline and to have Bill Clinton’s dragged through the mud. He would arrive to the administration at a time when Democrats are raising alarm bells about executive overreach and even some Republicans are growing uneasy about Trump’s brazen dismissal of FBI concerns that his campaign may have illegally colluded with Russia. Some people have even raised the specter of Richard Nixon, who famously proclaimed that, “when the president does it, that means that it is not illegal.”
But that's not true, and Conway understands this better than most. Before he was Trump's hire, before he was Kellyanne's husband, even before he was a right-wing co-conspirator, he was a lawyer who caught the eye of some Jones allies with a column in the Los Angeles Times. The essay methodically dismembered Bill Clinton's argument at the time that presidents should be considered immune from litigation that could distract from their official duties.
“No Man in This Country . . . Is Above the Law.”
Correction: An earlier version of this story stated that Conway's email to Matt Drudge about Bill Clinton was a violation of a gag order. It has been updated to note that Conway denies this. The story also stated that Conway's mother was a nurse. She was an organic chemist.