When Conservative Justices Revolt

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