Mark Peterson / Redux

Until two months ago, Leonard Leo was among the unambiguous winners of the Trump era. The bookish lawyer and architect of the conservative legal movement has spent the past three and a half years executing his decades-long vision of remaking the federal judiciary—he was instrumental in the Supreme Court appointments of Brett Kavanaugh and Neil Gorsuch. But during the Court’s term this summer, an old conservative nightmare recurred: Republican-appointed justices, including Gorsuch, aligned with their liberal colleagues on big, consequential decisions about immigration, abortion, and LGBTQ protections.

In recent decades, conservative justices have consistently moved to the left once reaching the bench: Anthony Kennedy, who was nominated by Ronald Reagan, routinely cast the deciding vote against social conservatives on gay rights. Conservative-movement stalwarts have never forgiven David Souter, the George H. W. Bush appointee, for voting to uphold the constitutional right to abortion in the 1992 decision Planned Parenthood v. Casey, or for siding with his liberal colleagues in the battle over the 2000 presidential election, Bush v. Gore. Leo spent his career building a conservative legal machine in Washington that would forestall this kind of leftward drift among Supreme Court justices. But this summer, the machine began to sputter.

As the longtime executive vice president of the Federalist Society, the influential network that cultivates conservative lawyers, Leo developed a massive Rolodex of potential judicial nominees who are skilled at repeating shibboleths that show their ideological leanings while making sure they can still get confirmed to the bench. “Our job is not to seek particular outcomes,” Leo told me by phone recently. “Our job is to find people who are going to demonstrate fidelity to the Framers’ Constitution, and to the laws as they are drafted and passed by Congress or the states.” Leo, who worked on confirmations for the White House separately from his work at the Federalist Society, recently left his day-to-day role at the organization to focus on CRC Advisors, a group he described vaguely as an effort to make the conservative movement “more effective, more strategic.”

Leo’s greatest strategic success, perhaps, has been convincing Donald Trump of his methodology: He helped Trump craft a list of potential Supreme Court nominees during the 2016 presidential campaign, which Trump widely advertised to demonstrate his conservative bona fides, and, in less than four years, Leo has shepherded 200 judges to their confirmation on the federal bench. But the president—and his supporters—made a pact premised on results. If even Leo can’t guarantee conservatives the rulings they crave, can Trump?

If Trump wins reelection in November, he will likely get to solidify the Supreme Court’s rightward tilt, perhaps for decades, as seats potentially open up. Eighty-seven-year-old Ruth Bader Ginsburg was hospitalized in mid-July for a possible infection, and she recently announced that she is undergoing chemotherapy for a recurrence of cancer. Her liberal colleague Stephen Breyer is also an octogenarian. Conservative-movement activists were frustrated by setbacks at the Court this term, even going so far as to question Trump’s judicial vetting process. But Leo is taking the long view, arguing that his movement’s philosophical overhaul of the judiciary will yield dividends for years to come.

The conservative legal movement was born of political mergers. “Within groups like the Federalist Society, you have such a huge range,” Carrie Severino, an ally of Leo’s who advocates for conservative judges through her organization, the Judicial Crisis Network, told me in an interview. “You’ve got Never Trumpers, you’ve got Always Trumpers, you’ve got libertarians, you’ve got conservatives.” Leo straddles these worlds: He’s a devout Catholic who once told The New Yorker that abortion is “an act of force” and “a threat to human life,” but he’s also the master networker of the elite conservative legal world, which is dominated by libertarians intent on limiting the size of government and rolling back regulation. Although ideologically disparate, these conservative groups are united by twin judicial philosophies that Leo is fond of declaiming in conversation: textualism, which holds that judges should interpret laws based on the plain meaning of their words, and originalism, which points to the Founders’ original intent for interpretations of the Constitution.

Conservative legal activists also find common cause in their fear that American culture is becoming more dogmatically progressive, and judges will be swept along with it. “Trump’s judicial nominating process was actually designed to avoid choosing justices who, as he characterized Chief Justice Roberts in his Obamacare decision, are ‘weak,’” Severino said. Trump specifically asked potential Supreme Court nominees why they think past justices have shifted to the left, she said, and looked for nominees with “a backbone” and “the courage of their convictions.” Members of Trump’s vetting team, including Leo, prized these qualities because they believe good judges must at times be willing to defy prevailing cultural norms, especially on contentious social issues such as abortion and homosexuality. Decisions that favor progressives are “used as weapons” against conservatives, “and that is frightening,” Kristen Waggoner, the general counsel of Alliance Defending Freedom, a conservative law firm focused on religious issues, told me. “The political and cultural winds shift, but our constitutional rights should not.”

As they did for Trump’s other Supreme Court prospects, Leo and his team reviewed Gorsuch’s record for what they saw as independence and fearlessness. “His judicial record demonstrates a faithful commitment to the Constitution and the rule of law,” Senator Ted Cruz of Texas said at Gorsuch’s confirmation hearing. “He has refused to litigate his own policy preferences from the bench.” In mid-June, however, Gorsuch shocked conservatives by writing the opinion in one of the biggest cases of the term, consolidated under Bostock v. Clayton County, arguing that federal civil-rights law protects LGBTQ employees from discriminatory practices. Conservatives have long argued that Congress never intended for Title VII, the provision that bars employment discrimination, to cover sexual orientation and gender identity—otherwise, legislators would have explicitly said so. Gorsuch disagreed with this conclusion. Backed by Chief Justice John Roberts and all four of the Court’s liberals, Gorsuch wrote that he reached his decision in favor of LGBTQ rights using textualism, the conservative judicial philosophy. “It’s no contest,” he wrote. “Only the written word is the law, and all persons are entitled to its benefit.”

Leading conservative lawyers in Washington were shocked. “It would be disingenuous to say that we’re not deeply disappointed,” said Waggoner, whose firm represented one of the losing parties in the consolidated Title VII cases. “The three branches of government best serve Americans when each stays in its lane.” Cruz called Gorsuch’s opinion “lawless,” telling reporters that the justice had “just put on the hat of a legislator and said, ‘Guess what, I’m writing federal statute all on my own.’” Senator Josh Hawley of Missouri, who wrote a glowing CNN op-ed in support of Gorsuch’s nomination to the Supreme Court, decried Bostock on the Senate floor as a flashing sign of danger for religious conservatives, who fear that extending civil-rights protections to LGBTQ people will threaten their freedom of conscience. “If this case makes anything clear, it is that the bargain that has been offered to religious conservatives for years now is a bad one,” Hawley said. In exchange for going along with the conservative establishment, religious voters are promised judges who will protect their rights, he said, but those judges consistently fall short. “It’s time for religious conservatives to stand up and speak out, rather than being told to sit down and shut up,” he said.

Leo refused to comment on his personal views about the Bostock case, but defended Gorsuch’s conservative credentials. “Everything that Neil Gorsuch had written prior to Bostock strongly suggested that he was very committed to textualism,” he told me. Some conservatives may find Gorsuch’s approach overly literal, he said, but that’s just a matter for conservatives to debate. “Sometimes, originalists and textualists just misapply those doctrines,” he added. “That may make someone wrong. It doesn’t necessarily make them unprincipled. And there’s a difference.”

Bostock was just the beginning of bruising conservative defeats during this term. In June Medical Services v. Russo, the Court’s first big case on abortion since Trump was elected, Roberts cast the deciding vote to strike down a Louisiana law that regulated abortion providers. This was a “disaster,” Hawley tweeted. “It is a big-time wake up call to religious conservatives. We must make our voices heard. And time for [a] hard look at vetting & selection process.” This week, the senator told The Washington Post that he would only support Supreme Court nominees who had previously publicly stated that Roe v. Wade was wrongly decided.

As the term produced one defeat after another—on abortion, LGBTQ rights, immigration, and tribal affairs, conservative justices leading the way each time—the sniping from conservative commentators grew more pronounced. If these are the conclusions a majority-conservative Court comes to, they asked, is the conservative legal machine really as effective as Leo and his allies have claimed?

“There’s certainly going to be some areas that people are going to be disappointed with,” Leo said. But “if you look at where the Supreme Court is today, versus where it was 25, or 30, or 40 years ago, there’s no way that I would trade today’s Court.” Leo, who is in his 50s, has been an influential player in Republican judicial appointments for more than two decades. “We’re having a conversation about whether an application of originalism or textualism could be … botched, as opposed to whether originalism and textualism are abandoned altogether in favor of a more activist kind of overreach,” he said.

Leo defended the Trump administration’s vetting, which he says has been inclusive of religious conservatives. Historically, judicial vetting has been a “narrow, secretive, less transparent, less accountable process” with “scant records and very little broad public involvement in the debate about the selection,” he said. Trump made it clear who he was considering and gave all players in Washington plenty of time to determine whether his choices passed ideological muster. “I don’t know any religious conservative who, when aware of this history, would want to revert to the kinds of selection and vetting processes we had in the past,” Leo said.

If black-tie dinners ever return, Roberts, not Gorsuch, is most likely to get the cold shoulder over champagne and canapés at Federalist Society events. “I have a lot of friends in the movement, and we talk and text. I feel people are disappointed in Gorsuch. But they’re not angry at Gorsuch. They’re really angry at Roberts,” John Yoo, a law professor at UC Berkeley, who is known for producing the memos that justified the George W. Bush administration’s use of torture against detainees, told me. Roberts’s defection on this term’s abortion- and LGBTQ-rights cases were just the latest of his conservative betrayals, including defending the Deferred Action for Childhood Arrivals program for children brought to the United States illegally, and batting down an effort to add a citizenship question to the 2020 census.

Roberts was the last of the “‘wink, wink, nod, nod’ conservatives,” Yoo told me—nominees who were understood to be conservative, but who didn’t have a fierce record of divisive or ideological statements. “If you look at the Trump lower-court nominees, they are people who aren’t ‘wink, wink, nod, nod’ conservatives. They’re ‘hit you in the head with a 2-by-4’ conservatives,” he said. “That trend is going to accelerate.”

The end of the Supreme Court term brought a slew of religious-freedom cases that sweetened an otherwise bitter term for social conservatives. The Court protected the rights of religious schools to participate in state-sponsored voucher programs, and to oversee the hiring and firing of religion instructors. It also confirmed that religious nonprofits do not have to provide birth-control coverage under the Affordable Care Act. In these decisions, the justices acknowledged that religion and “rights of conscience are essential to protect, because they are the core of what constitutes individual worth and human dignity,” Leo said.

Trump has spent the past month making the case that religious conservatives need him to protect their legal rights. “If the Radical Left Democrats assume power, your Second Amendment, Right to Life, Secure Borders, and … Religious Liberty, among many other things, are OVER and GONE!” he tweeted. He promised to release a new list of potential Supreme Court nominees by September 1, and added the current justices to a long list of his political enemies: “Do you get the impression that the Supreme Court doesn’t like me?” he tweeted. Like the president they support, religious conservatives are likely discontent with this term at the nation’s high court. And yet, their defeats may only redouble their commitment to supporting the president.

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