George Conway’s Manhattan law firm sits near the corner of Sixth Avenue and 52nd Street, just three blocks from Trump Tower.
During the 2016 election, when he still supported Donald Trump, the corporate litigator would sometimes walk over to the campaign HQ after work, according to former campaign aides. He’d pop in around 8 p.m. and would sit and work in his wife Kellyanne Conway’s office until she was ready to go. Then he’d drive her to New Jersey, or the couple would share a town car home.
Friends say he was proud of Kellyanne, the longtime Republican operative who was finally running the show, and the evening routine allowed him to grab some one-on-one time with his busier half. On Election Night, he cried, and noted to other campaign aides that as the first female campaign manager of a winning presidential bid, his wife had made history.
Over the past year, however, since Trump fired former FBI Director James Comey and special counsel Robert Mueller was appointed by the Justice Department, George Conway has become a man in turmoil. A serious, conservative attorney who believes in the rule of law, he has been torn, people who know him say, between the loyalty he feels toward his wife and an assault on his profession and his ideals that he did not anticipate when he cheered on Election Night — delivered by her boss.
During that period, he has walked away from a powerful job running the Justice Department’s civil division, where he would have served as one of the administration’s top lawyers. And he has become a Twitter phenom — tweeting and retweeting critiques of the president and support for the Mueller probe that his wife’s employer calls a “witch hunt.” Many in the White House have noticed, including Kellyanne and, according to multiple administration officials, the president himself.
The pushback coming from inside the house of Trump’s lead cable news defender has become one of Washington’s favorite family dramas. In “Conway versus Conway,” George attacks the president, or seems to defend the Mueller probe, while Kellyanne puts her own credibility on the line to defend Trump, who has escalated his verbal assaults on the Russia inquiry and this week even demanded an investigation of the investigation.
Conway now has nearly 50,000 followers, and his tweeting — the majority of it retweets, rather than his own commentary — has attracted the notice of everyone from conservative legal scholars to TV host Whoopi Goldberg, who gave him a shoutout on a recent episode of ABC’s The View: “I say George, keep it up, honey. Whether your wife gets it or not, stay sane. It’s a good thing to stay sane.”
Asked to explain his public feud with his wife’s boss, Conway declined to comment or elaborate on his tweets. “If I wanted to say anything publicly,” he said in a direct message on Twitter, “I would just say it.”
But friends and professional acquaintances say Conway’s tweets are just the tip of an iceberg of frustration with Trump that has only grown over the past year. While Conway has always been known as a contrarian, however, some friends have been surprised and disappointed by the public airing of anti-Trump sentiment from a man who is known to value discretion.
On some occasions, Conway has even gone outside the boundaries of Twitter when he can’t contain his apparent grievance any longer.
“Drivel,” he told Reuters in an interview last week, referring to Rudy Giuliani’s assertion that the president cannot be the subject of a subpoena. He has also emailed people who have written things critical of Trump and quietly suggested improvements in their arguments, according to people who have received his unsolicited two cents.
As Conway has stayed mum, his tweets have sparked more questions than answers: The Washington Post has wondered if he is trying to sabotage his wife. The Huffington Post asked, “Would it be too wild a leap for a Trump Kremlinologist to think this might be a prelude to Kellyanne Conway’s own White House departure?”
But in conservative legal circles, his tweets are reverberating in a way that has not much at all to do with his wife. There, George Conway is seen as rebuking the silence of his fellow Federalist Society members — the elite, conservative lawyers who have generally chosen to give Trump a pass on his breaches of long-cherished legal norms and traditions in exchange for the gift of Supreme Court Justice Neil Gorsuch.
George Conway’s tweets would be somewhat less notable if he were not one of the few members of his exclusive insular tribe — a Morton’s Steakhouse kind of crowd made up of former law clerks, Republican administration appointees and university professors — who has been publicly critical of the president and seemingly supportive of the Mueller probe.
By keeping its collective mouth shut, the Federalist Society — a nationwide network of conservative lawyers with its power base in D.C. — has amassed huge influence in the Trump administration, essentially hand-selecting not only Gorsuch but recruiting ultra-conservative judges to fill vacancies on appellate courts on down. It’s a status the organization does not want to jeopardize through rash tweets or the signing of petitions that might make one feel good on issues that matter less to them than a complete reorientation of the federal bench.
The executive vice president of the Federalist Society, Leonard Leo, has called around to prominent lawyers and funders in town, warning them not to get on the wrong side of the Trump administration, according to a source who was briefed on the calls. After all, Leo expects to play a lead role in at least one more Supreme Court pick during Trump’s tenure. (Leo did not return calls for comment.)
At times, the society has even broken with the mainstream of the conservative legal establishment in its effort to stand with the administration. On Friday, for instance, the Federalist Society is hosting a call “examining the legality of the Mueller Investigation.” The featured speaker is Steven Calabresi, a law professor and co-founder of the organization who has argued that Mueller’s probe is unconstitutional. Calabresi also happens to be a friend of Conway’s — it’s a small, Federalist Society world, after all.
“I’ve known him for 30 years, and George follows what George thinks,” Calabresi said in an interview. “He speaks his own mind. if I were George, I wouldn’t do this. But his tweets do not come as a surprise to me.”
They may not be a surprise, but they’re not always welcome from the Federalist Society crowd, which views Trump critics in the foreign policy arena — people like Bill Kristol and Elliott Abrams who were publicly critical of the president during the campaign — as a cautionary tale. Those critics were locked out of powerful posts where they could have tried to shape policy from inside the room. Instead, they are left shouting from the green rooms of MSNBC, while the Federalists are quietly delivering on their agenda.
It’s what some critics view as a deal with the devil. “Their silence has been a big problem,” said Kristol, the neoconservative founder of the conservative Weekly Standard, and a prominent Never-Trumper. “It’s let Trump get away with too much on the rule of law front, where the most natural and informed people haven’t stepped up to say anything,” he said. “Having big-name conservative lawyers consistently rebuking Trump could have made a difference. Their silence is taken as acquiescence.”
Kristol added: “Institutionally, I suppose the Federalist Society has never done better. In terms of speaking truth to power, on the other hand, it’s never been more silent.”
That silence has made Conway’s voice echo in the void. His tweets become chyrons on cable news and are a topic of discussion on The View because of whom he married. But they resonate in Washington power circles because they cast doubt on the entire project of his peers: Here is a well-respected, die-hard conservative member of the club—who has more personally invested in defending the administration than most—and he doesn’t seem to agree with the argument that it’s worth it to bite your tongue.
In an interview, Calabresi admitted that Conway may be giving voice to what other members of the Federalist Society think but are too scared to say. “There is a range of viewpoints about Trump, including some people who are Never Trumpers but have been quiet about it, in part because of the judicial nominations,” he said.
But after Conway attacked his own argument that the Mueller probe is unconstitutional, Calabresi called back to amend his comments. “At this point, George is very far off the reservation of what many Federalist Society people think,” he said.
Conway, a Massachusetts native, was transformed from a Scoop Jackson Democrat to a Reagan Republican on the manicured quads of Harvard University as an ambitious young freshman who graduated at age 20. In 1980, he supported John Anderson, the Republican congressman for Illinois who ran for president as an independent. But in Ronald Reagan, George Conway was quickly won over by a president whose free market, strong defense policies made sense to him.
As a Yale Law School student in 1984, friends remember George Conway blasting “God Bless the USA” – the theme song of the Republican National Convention that year – out his windows, a show of support for Reagan meant to troll the predominantly liberal student body on campus.
He became head of the Yale Law School chapter of the Federalist Society.
After law school, he went on to clerk for Judge Ralph Winter, a libertarian iconoclast whose other prominent clerks included Fox News’ Laura Ingraham and the president’s newest lawyer, Emmet Flood.
To understand the tweets, friends say, one has to trace a thru-line of Conway’s contrarian streak that dates back to his “God Bless the USA” stunt. Several pointed to other memorable “George being George” moments throughout his career—with the targets being Republicans and Democrats alike.
In 1994, for instance, George Conway wrote his first and only op-ed: a piece for the Los Angeles Times entitled “No Man in This Country Is Above the Law.” In it, he argued against presidential immunity for Bill Clinton in the civil suit brought by Paula Jones, who he was secretly helping with legal aid. (It was during his time working behind the scenes on behalf of Bill Clinton’s accusers that he became friends with Ann Coulter, who set him up with a bright young conservative named Kellyanne Fitzpatrick.)
In 2005, Conway broke with his party to join a group of conservatives in forming BetterJustice.com, which staged a PR blitz calling on President George W. Bush to drop his nomination of Harriet Miers to the Supreme Court. Conway’s objection, according to friends, was that she simply hadn’t thought enough about the issues of legal constitutionalism to merit a seat on the country’s highest court.
“The two people who brought down Harriet Miers were George Conway and Bork,” said Calabresi. “I’m sure he supported the Bush administration. But George does not follow the party.”
It was after the election and before Comey’s firing that Conway, wearing his proud husband cap, gave up his partnership at Wachtell, Lipton, Rosen & Katz to move to a city where his prestigious New York law firm doesn’t even keep an office. He became “of counsel” to the firm where he has worked since he was 25, a demotion that also comes with a pay cut.
Now, the man famous in legal circles for arguing a major securities case before the Supreme Court and winning in an 8-0 vote decided by the late Justice Antonin Scalia works from home or commutes to Manhattan a few days a week.
“This is an adjustment for him and a big one,” said David Lat, founding editor of the legal news site Above The Law, who was friends with Conway when he worked as a lawyer at Wachtell. “At George’s age, it’s very unusual to give up partnership.”
But when the Conways first moved their family of six to Washington for Kellyanne’s amorphous new West Wing assignment, George Conway was in line for a public-sector job that would have been a bigger lift than being a well-paid partner in his law firm. Last year, around this time, he was deep into the process of putting together the extensive paperwork required to be nominated to head up the Justice Department's civil division.
Conway had already completed a background check and was interviewing candidates to be his deputy when Comey was fired, according to sources familiar with the paperwork process. It was around that time that he started telling potential colleagues that he was having second thoughts about the whole thing. It just didn’t make sense, he told them, for he and his wife to both be in targets in the Trump whirlwind at the same time.
In a statement at the time, he said: “Kellyanne and I continue to support the President and his Administration, and I look forward to doing so in whatever way I can from outside the government.”
On June 5, 2017, days after officially announcing that he was out of the running for the top slot at the DOJ, he took to Twitter to note that the president’s tweet about his travel ban could actually hurt its chances in court.
And thus, a Twitter star was born.
People who know Conway read the tweets not as any betrayal of his wife but rather as someone who is restraining himself for her benefit, and who would be much more outspoken if it weren’t for her current job. Maybe he would be writing more op-eds, they say. Or speaking out in other ways. But under the constraints of his current situation, the retweet is the perfect crime: It allows Conway to unload without, exactly, unloading.
Even so, friends have warned him, at times, that even just his retweets are attracting too much attention and that he should stop – for his own professional reputation, as much as his wife’s. So far, he hasn’t heeded their advice.
Conway joined Twitter in 2012, but he didn’t become an active user until the Trump era. He follows a little over 700 accounts, including the Drudge Report, the Federalist Society, most of the reporters that make up the White House press corps, Comey, an anonymous account that goes by the name of “Rogue Snr WH Adviser,” Former U.S. Attorney Preet Bharara, and about 20 feeds devoted to pictures of corgis.
“He’s not a wallflower; he’s not a guy who blends into the background,” said Lat. “Twitter is a place where he can assert his independent identity.”
Kellyanne Conway’s allies in the White House have worried, at times, about her husband’s tweets – worried about how they will be wielded in the snakepit environment of the communications department, where enemies might try to use her husband as a weapon against her. “I had some angst for her,” said one former administration official. “My anxiety was that he was putting Kellyanne in a bad spot. But I don’t think it affected her at all. Her standing with the president is rock-solid. She’s as loyal as it gets – sometimes to a fault.” The source added: “I would say the likely impact of George’s tweets inside the White House is negligible.”
And while the general reaction from inside the building was a giant “WTF” when he started expressing disagreement with the administration, a year in, they are generally now viewed with nothing more than an eyeroll: It’s weird, but it’s just George being George. Most people now view his wife as one of the last inner-circle aides left whose loyalty the president counts on. One administration official said Kellyanne Conway is so close with the president that she would feel comfortable flagging her husband’s tweets for the president herself.
But Kellyanne Conway, a master of deflection, has doubled down instead, when confronted with questions about her husband’s tweets. In an interview earlier this month, she accused CNN’s Dana Bash of trying to “harass and embarrass” her by asking her about his tweets. She also declined to comment for the story.
She has told people, however, that she is hardly the only administration official whose spouse is critical of the president – and that there are even people working in the White House who didn’t vote for Trump.
“This is not Mary Matalin and James Carville,” said former Harvard University Law professor Alan Dershowitz, a lifelong Democrat who has become one of Trump’s main legal defenders on cable news. “These are both conservative Republicans. One of them has a job to do and she has to only say positive things. He doesn’t have a job to do. Each one has to be judged by the job, and the context. I could see someone saying, ‘My wife does this, so I’m going to keep my mouth shut.’ But he’s not that kind of guy.”
Dershowitz doesn’t know George Conway personally, only by way of reputation. But as someone with a similar contrarian streak, Dershowitz said he understands why George Conway can’t just shut up. “I have friends who say, ‘Everything you say is right, but you should shut the fuck up,’” said Dershowitz. “The answer to that is, people like Conway and me, we can’t. Part of being married is being an independent person.”
That independence doesn’t seem to be dissipating any time soon.
Last weekend, Kellyanne Conway appeared on CNN to defend the president’s morning tweetstorm. “I will tell you that over a year into this that there is no evidence of collusion,” she said. “The president has called this investigation a witch hunt many times.”
Her husband was busy spouting a different line. After the president tweeted that he was demanding the Justice Department launch an investigation into whether it spied on his campaign, George retweeted former DOJ prosecutor Carrie Cordero, a prominent defender of the Mueller probe. “The Department of Justice doesn’t open investigations for political purposes,” she wrote, “which is what the president says today he will order tomorrow. There are rules. And I’m convinced there are people left in this administration who will follow them.”