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Does the Federalist Society Still Need Trump?

The conservative legal organization got what it wanted from the president. Will more of its members start speaking out against him?

Alex Wong/Getty Images

The Federalist Society is convening in Washington on Thursday for its annual convention, a Comic-Con of sorts for the conservative legal movement. It’s been a blockbuster year for those in attendance. The confirmation of Justice Brett Kavanaugh last month cemented a reliable conservative majority on the Supreme Court for at least a generation. Judicial nominees for the lower courts are sailing through the Republican-led Senate at a breakneck pace. Those victories made George Conway’s announcement on Wednesday all the more striking.

Conway, a prominent Washington lawyer with deep conservative ties, announced the formation of Checks and Balances, which describes itself as “a group of attorneys who would traditionally be considered conservative or libertarian.” This is a bit of an understatement: The group’s 14 founding members are a medley of high-profile academics, litigators, and former government officials, including a former Cabinet secretary. Its brief mission statement is a straightforward summary of the basic tenets of small-r republicanism. Though President Donald Trump is not mentioned by name, he is unmistakably the target.

“We believe in the rule of law, the power of truth, the independence of the criminal justice system, the imperative of individual rights, and the necessity of civil discourse,” the statement says. “We believe these principles apply regardless of the party or persons in power. We believe in ‘a government of laws, not of men.’” It closes with a rallying cry: “We seek to provide a voice and a network for like-minded attorneys to discuss these ideas, and we hope that they will join with us to stand up for these principles.”

There’s always been an inherent contradiction in the conservative legal movement’s relationship with Trump. On one hand, the president has delivered them an unparalleled string of victories and decisively shifted the federal judiciary to the right. At the same time, the president has weakened the American rule of law, campaigned to turn the Justice Department into a political weapon, and used his office to threaten journalists and political opponents.

It’s been an open question when—or even if—the movement would reach a breaking point with him. That day may now come sooner rather than later.

“Some of us have been raising these concerns for a while,” Jonathan Adler, a Case Western University law professor who signed the mission statement, told me. “I’ve been open about criticizing the administration where I thought that was necessary from the beginning, and being positive where there are things to be positive about. But I think some people have needed a few straws on the camel’s back before they’re willing to be more open about it.”

Conway, as the husband of White House counselor Kellyanne Conway, may be the most recognizable name to the general public. But the rest of its members are all prominent figures in conservative legal circles and veterans of past Republican administrations. Tom Ridge served as the first secretary of Homeland Security. Peter Keisler was tapped to replace Chief Justice John Roberts on the D.C. Circuit Court of Appeals in 2005, only to be rejected by Democratic senators for his conservative background. Orin Kerr, a University of Southern California law professor, is the Supreme Court’s go-to scholar on Fourth Amendment matters.

The question is whether other Federalist Society members, who have been hesitant to speak out, will answer the group’s call. There’s reason to believe so—precisely because they have been gotten what they wanted under Trump. As his first term—and perhaps his presidency—winds down, Trump may become a victim of his own success, as diminishing returns in judicial policy make it harder for the conservative legal community to stomach him.


The Checks and Balances group sprang from informal conversations between him and the other members over the past year, according to Adler, who helped craft the legal argument behind the Affordable Care Act challenge in King v. Burwell. Over the “last several weeks,” he said, those discussions turned toward forming an organization and making some kind of public declaration. The goal was to provide a space for other like-minded conservative and libertarian legal figures to express concerns about the Trump administration and its threats to the nation’s constitutional order.

Other conservative legal figures have been outspoken about Trump in recent weeks. Ted Olson, a former solicitor general and the victor of Bush v. Gore, signed on to represent CNN in its First Amendment lawsuit against the White House for revoking correspondent Jim Acosta’s press credentials. John Yoo, who took a maximalist approach to executive power under President George W. Bush, wrote in The Atlantic that Trump violated the Constitution by naming Matthew Whitaker to be acting attorney general after his boss, Jeff Sessions, was forced to resign. (George Conway published a similar argument in the New York Times last week, co-written by Obama DOJ veteran Neal Katyal.) Adler and others criticized Trump’s threat to end birthright citizenship by executive order on originalism grounds.

With few exceptions, liberal members of the American legal community have warned since the beginning that Trump posed a threat to American democracy. Many nonpartisan law professors also joined criticism of the travel ban directed at Muslim-majority countries, the administration’s separation of migrant families at the border, and other extreme policies. Legal critiques from the right, however, have been more sporadic until recently. Trump, as a presidential candidate, had struck a Faustian bargain of sorts with top figures in the conservative legal movement: In exchange for outsourcing judicial nominations to them, they would not oppose his takeover of the Republican Party.

His rise to power came at a fateful time for the movement. Since the 1960s, legal conservatives have dreamed of building a Supreme Court that mirrored their ideological worldview. Justice Antonin Scalia’s sudden death in 2016 imperiled decades of work to reshape the federal judiciary in their own image. The possibility that President Hillary Clinton would name his replacement kept the fracturing Republican Party together even as Trump assumed control of it. On Election Night, the gambit paid off. Instead of witnessing the first five-justice liberal majority on the court since Earl Warren, Republicans have now installed justices Neil Gorsuch and Brett Kavanaugh, securing the court’s ideological makeup for decades. More than 80 federal judges have also been confirmed over the past two years, steadily reshaping the lower courts.

Those accomplishments thrilled conservatives of all stripes. They also kept quiet many in the conservative legal community who had concerns about the Trump administration’s other policies, Adler said. “Last year at the Federalist Society conference, there were press reports about the ‘But Gorsuch’ stress ball,” he noted. “And it’s significant that they were ‘but Gorsuch,’ not ‘and Gorsuch,’ right? And it was a stress ball. The reason I think it was so popular is because there are a lot of people in FedSoc who are happy about judicial nominations, and were hoping that the judicial nominations would outweigh other things.”

The American left tends to picture the Federalist Society as a monolithic institution, one that grows originalist judges from giant cloning vats in its basement. In reality, it functions more like a decentralized social network and debate club, one where reputation is the coin of the realm. Checks and Balances’ members are effectively using that currency to provide cover for others who may fear professional reprisals from a vindictive White House, and to preemptively defuse attempts to paint members as conservative apostates.

“Concerns that I endorsed about the birthright citizenship proposal are based on the original public meaning of the constitutional text,” Adler noted, referring to Trump’s threat not to guarantee citizenship to everyone born in the U.S. “Criticism about the Justice Department not being sufficiently nonpartisan are based on traditional principles about what the role of the Justice Department is and what the role of law enforcement is.... We’re not abandoning our prior ideological affinities. In many ways, we’re seeking to reinvigorate them and see that they are upheld in this more challenging environment.”

It’s worth noting that liberals are no stranger to devil’s bargains themselves. Many Democrats brushed aside Bill Clinton’s sexual misconduct in the 1990s because of their support for his policies and desire to keep Republicans out of the White House. Today, the American left might be skeptical of making common cause with their ideological adversaries, and rightly so. Many of those adversaries stayed silent over the past two years as Trump relentlessly weakened American democracy—and quietly applauded as he delivered one staunch conservative to the courts after another.

But if, as 2020 nears, Trump’s reelection chances are slim and no Supreme Court justices retire or die—two very big ifs, admittedly—the number of conservative critics may well grow. “I think there are quite a number of people that do have conflicts, and I think for a lot of people that conflict’s grown over time,” Adler said. “I think there are also people who think the administration’s ability to produce silver linings that outweigh the cloud is diminishing. If that means more people who are willing to criticize the administration when it does wrong, that’d be good.”

Perhaps some of these people will feel that the rule of law has become significantly more imperiled than it was in Trump’s early years. Others may simply conclude that, after the decisive rightward shift of the Supreme Court and the transformation of the most important lower courts, it is time to burnish their reputations for the post-Trump era. Whatever their reasons, the left ought to welcome them to the resistance.

I’m reminded of a high-school math teacher who would penalize me on a test when I got a question correct but used the wrong method. Sometimes, how one gets to the right answer matters less than getting there at all.