When Samuel Alito appeared before the Senate Judiciary Committee for his 2006 confirmation hearings, one dramatic moment stood out above all others: the time his wife, Martha-Ann Alito, burst into tears and stormed out of the room over what she perceived as unfair attacks on her husband.

While barely remembered today, the incident proved pivotal, instantly generating sympathy for the nominee and his aggrieved spouse. Fearful of looking like bullies, Democrats by and large lost their ardor to block his confirmation. When after a short break, Alito walked back into the hearing room, holding his wife’s hand and kissing her on the cheek, his White House sherpas were ecstatic. “It was game, set, match,” recalls Steve Schmidt, the veteran operative tapped by President George W. Bush to quarterback the Alito nomination.

Today, 18 years later, Martha-Ann Alito’s tearful protest takes on new relevance following the disclosure by The New York Times that it was she—apparently enraged over a crude insult from an anti-Trump neighbor—who unfurled a “Stop the Steal” symbol, an upside-down American flag, outside the couple’s northern Virginia home weeks after the January 6 attack.

“Game, set, match”: Martha-Ann weeps at her husband’s confirmation hearing, in 2006.

To what extent Alito was complicit in this unusual form of political protest is unclear; one neighbor told The Washington Post that the flag was up for anywhere from two to five days, making it hard to believe that the justice was unaware that his home was being used to promote the cause of the Capitol insurrectionists.

Fueling the controversy further, The New York Times on Wednesday reported that an “Appeal to Heaven” banner—adopted in recent years by apostles of the Christian Nationalist movement and also spotted among the January 6 rioters—flew above the Alito’s New Jersey summer house as recently as last year.

With even senior Republicans questioning Alito’s judgment, the upside-down flag flying over the Supreme Court justice’s front yard seems an apt symbol of his emergence as the staunchest, most uncompromising and defiant hard-right member of the Court—a role some say was entirely foreseeable when Democrats lost their nerve to challenge his nomination nearly two decades ago.

Shy and socially awkward with fiercely conservative views shaped by his Catholic upbringing—hence his authorship of the Dobbs decision, wiping out abortion rights—Alito appears to have now replaced Clarence Thomas as the most polarizing, not to mention ethically challenged, member of the Court. “Nobody likes him,” says Schmidt, a pugnacious operative who spent countless hours with Alito throughout the confirmation process. “He’s sullen, aggrieved, prickly, and angry.”

Schmidt has undergone a political transformation since his days as a spinmeister for Dick Cheney and Karl Rove, emerging as an outspoken Never Trumper with no shortage of biting comments about the failings of his former ideological allies. But there is at least some evidence that Alito’s colleagues on the Court have shared similar views.

“He’s sullen, aggrieved, prickly, and angry.”

Sandra Day O’Connor, a pragmatist to the core, whom Alito replaced on the Court, was privately embittered by the rigidly conservative opinions authored, or joined, by her successor. “She was furious about Alito,” said the late Walter Dellinger, Bill Clinton’s solicitor general and a friend of O’Connor’s. According to a passage in Evan Thomas’s biography of the first woman Supreme Court justice, “she viewed him as a betrayal of her legacy.” Perhaps even more telling, she had little use for him on a personal level. “He has no sense of humor,” O’Connor groused to another friend, according to Thomas’s account.

Alito’s friends say that Alito, while shy and retiring, does have a dry sense of humor. But more importantly, they argue, what do you expect given the harsh treatment he’s gotten from the news media and liberal legal establishment?

“He’s Italian; he’s from New Jersey,” says retired New Jersey Superior Court judge Andrew Napolitano, an old college classmate of Alito’s and longtime friend of the couple, acknowledging that the media scrutiny has gotten under his skin. But if anything, it is Martha-Ann Alito—more loquacious and an ardent “conservative Republican”—who resents the attacks even more, he says. “It does not surprise me” that she would have reacted to the quarrelsome neighbor the way she did, says Napolitano. “She doesn’t suffer fools gladly.”

Perhaps stoking Martha-Ann Alito’s sense of grievance is that, as a wife of a Supreme Court justice, she has faced ethical questions about her own financial investments. Last year, the Intercept reported that Mrs. Alito had leased a 160-acre parcel of land in Oklahoma (which she had reportedly inherited from her father) to an energy company for drilling oil and gas under an arrangement that would give her more than 15 percent of the profits—a transaction that could theoretically become vastly more profitable depending on how the Supreme Court rules on cases challenging environmental regulations.

What emerges when talking to those who know Alito and his wife is a portrait of a couple who have seen themselves as outcasts in Washington ever since they arrived. “I mean, if you could see him [Samuel Alito], he just carries this deep resentment. And in part he never, never quite adjusted to life in the Washington area,” says one longtime conservative lawyer who has interacted with Alito at Federalist Society events over the years. And much of that resentment, the lawyer says, is fed by the overwrought personality of Martha-Ann.

“She hates Washington, hates living in Washington, hates the people in Washington. I think she feels socially isolated.... I do think there is this syndrome among some conservatives who come to Washington where they just feel completely socially isolated. And then it builds on itself. Because they get very insulted by, you know, how people treat them, and they become even more resentful. I do think that’s a phenomenon. And I think that’s a big part of whatever happened here.”

If so, it’s a phenomenon that has its roots in those long-ago confirmation hearings—in retrospect, a major, historical milestone in the creation of the Court’s now rock-solid conservative majority. Originally, Bush had tapped the smooth and engaging John Roberts, who had widespread bipartisan support, for the O’Connor seat. But when Chief Justice William Rehnquist died, Bush elevated Roberts for chief and at first turned to his White House counsel, Harriet Miers, to replace O’Connor. Then Miers ran into a buzz saw of criticism from movement conservatives—who viewed her as squishy on abortion and affirmative action—prompting the president to reluctantly replace her with the more ideologically reliable Alito after she withdrew.

Alito meets with then senator Joe Biden in 2005.

At first, it seemed a relatively safe pick. Alito had a commendable life story and an impeccable résumé. The son of an Italian immigrant who grew up in a working-class neighborhood of Trenton, Alito was a graduate of Princeton and Yale Law School and later served in the solicitor general’s office of the Justice Department during Ronald Reagan’s presidency. He had gone on to become a U.S. attorney in Newark and then a judge on the Third Circuit U.S. Court of Appeals, in Philadelphia. (Among those who recommended him to the White House was a fellow Third Circuit colleague, Judge Maryanne Trump Barry, sister of the future president.)

Alito also had the political and financial backing of a network of right-wing judicial activists just then finding its sea legs. One of those serving a key role on the White House confirmation team was then Federalist Society executive vice president Leonard Leo, who raised hundreds of thousands of dollars to run TV and online ads backing Alito—with much of the funding coming from billionaire real-estate magnate Robin Arkley, who popped up years later hosting Alito at his Alaskan fishing lodge during a lavish trip that the justice failed to report on his financial disclosures.

“She hates Washington, hates living in Washington, hates the people in Washington.”

But from the outset there were red flags for liberals. Alito had a clear track record on abortion rights: he was dead set against them. “I personally believe very strongly … that the Constitution does not protect the right to abortion,” he had written in a memo as a Justice Department lawyer, and he had an expansive view of gun rights, even voting as a lone dissenting judge to strike down a decades-old federal law banning machine guns.

But it was another issue entirely that led to the dramatic walkout by Martha-Ann Alito, which turned the tide in her husband’s favor. When he had applied for his job with the Reagan Justice Department, Alito had listed himself as “a member of the Concerned Alumni of Princeton, a conservative alumni group.” Discovering this in Justice Department files, Democrats pounced. The Concerned Alumni of Princeton was by then notorious for its strident activism.

In a magazine funded by the group, and edited by right-wing provocateur Dinesh D’Souza, its members had railed about Princeton’s decision to admit women and to recruit more Blacks. “People nowadays just don’t seem to know their place,” one article in the magazine The Prospect read. “Everywhere one turns, blacks and Hispanics are demanding jobs simply because they’re black and Hispanic.”

“It was a pretty outrageous group,” then senator Joe Biden told Alito after the nominee insisted he had no “specific memory” of joining the group or attending any of its meetings. As Democrats continued to berate Alito over the issue, Martha-Ann Alito sat directly by her husband, growing ever more furious. Ironically, it was questioning from a friendly Republican, Lindsey Graham, that finally set her off. “Are you really a closet bigot?,” Graham asked Alito, trying to help the nominee out. But when Martha-Ann Alito heard the question, her lips started to tremble and she wiped tears from her eyes. A family member tried to comfort her, putting an arm around her shoulder, before Mrs. Alito got up and fled the room.

Schmidt, who was watching from the back of the room, quickly called Fox News and other conservative media outlets to generate sympathetic coverage, and soon Megyn Kelly was calling the questioning about the Princeton alumni group “a new low.” Whatever the merits, the White House jujitsu seemed to have worked. Biden showed up the next day wearing a Princeton baseball cap, a sign he was taking the alumni group issue off the table. “[Alito] thought Biden looked ridiculous,” says Napolitano.

Still, as plans for a filibuster fizzled, paving the way for Alito’s confirmation on a 58–42 vote, there was a sense of foreboding among the Democrats. “I may be wrong about Judge Alito,” said Senator Dick Durbin, now the Judiciary Committee’s chairman. “If I am, no one will be more pleased. But I fear on this January morning in the Senate chambers, a chill wind blows, a chill wind which will snuff out the dying light of Sandra Day O’Connor’s Supreme Court legacy.”

Michael Isikoff is a veteran investigative journalist whose most recent book is Find Me the Votes: A Hard-Charging Georgia Prosecutor, a Rogue President, and the Plot to Steal an American Election