Leonard Leo is on the brink of achieving the goal he has been working toward for decades: a lasting conservative supermajority on the Supreme Court. Almost comically shadowy and conspiratorial, he can, at times, seem ripped from the pages of a Dan Brown novel. A member of the Knights of Malta, an archconservative Roman Catholic secret society, who has a taste for fine wine and tailored suits, he is judicial consigliere to the oligarch class—an expert at manipulating campaign finance law to funnel millions of dollars into the conservative political project.
For more than two decades, Leo has been working to remake the judiciary, stocking it at every level with right-wing apparatchiks. As one of his longtime allies told The Daily Beast two years ago, Leo knew that “conservatives had lost the culture war. Abortion, gay rights, contraception—conservatives didn’t have a chance if public opinion prevailed. So they needed to stack the courts.” He started working for the Federalist Society in 1991, two years after graduating from Cornell’s law school, and led its efforts to put John Roberts and Samuel Alito on the bench. Since then, he has built a vast network of shady nonprofits that fund ads and woo journalists whenever there’s a court fight. (Leo’s efforts aren’t strictly limited to the courts—he also has close ties to the firm behind the “Swift Boat Veterans for Truth” ads in 2004.) The Washington Post has estimated that between 2014 and 2017 alone, Leo brought in a quarter of a billion dollars for these groups. It was Leo who drew up the lists of conservative judges that Donald Trump released in 2016, promising to appoint one of them to the court if elected. Neil Gorsuch was on it. A year later, he’d suggest an old buddy, Brett Kavanaugh.
Leo’s power stems from his ability to raise money. In 2016, George Mason University announced that it would rename its law school for Antonin Scalia. As it turned out, Leo had raised the money to secure the name himself. Ten million dollars came from Charles Koch, another $20 million from a shell corporation that lists Leo as its president. It was only fitting—a law school was just the missing piece of an empire built around reshaping the American judiciary.