We Don’t Talk About Leonard: The Man Behind the Right’s Supreme Court Supermajority
ProPublica exposes this fascist.
If Americans had heard of Leo at all, it was for his role in building the conservative supermajority on the Supreme Court. He drew up the lists of potential justices that Donald Trump released during the 2016 campaign. He advised Trump on the nominations of Neil Gorsuch, Brett Kavanaugh and Amy Coney Barrett. Before that, he’d helped pick or confirm the court’s three other conservative justices — Clarence Thomas, John Roberts and Samuel Alito. But the guests who gathered that night under a tent in Leo’s backyard included key players in a less-understood effort, one aimed at transforming the entire judiciary.
The judges and the security detail, the law school leadership and the legal theorists — all of this was a vivid display not only of Leo’s power but of his vision. Decades ago, he’d realized it was not enough to have a majority of Supreme Court justices. To undo landmark rulings like Roe, his movement would need to make sure the court heard the right cases brought by the right people and heard by the right lower court judges.
Leo began building a machine to do just that. He didn’t just cultivate friendships with conservative Supreme Court justices, arranging private jet trips, joining them on vacation, brokering speaking engagements. He also drew on his network of contacts to place Federalist Society protégés in clerkships, judgeships and jobs in the White House and across the federal government. He personally called state attorneys general to recommend hires for positions he presciently understood were key, like solicitors general, the unsung litigators who represent states before the U.S. Supreme Court. In states that elect jurists, groups close to him spent millions of dollars to place his allies on the bench. In states that appoint top judges, he maneuvered to play a role in their selection.
Leo grasped the stakes of these seemingly obscure races and appointments long before liberals and Democrats did. “The left, even though we are somewhat court worshippers, never understood the potency of the courts as a political machine. On the right, they did,” said Caroline Fredrickson, a visiting professor at Georgetown Law and a former president of the American Constitution Society, the left’s answer to the Federalist Society. “As much as I hate to say it, you’ve got to really admire what they achieved.” Belatedly, Leo’s opposition has galvanized, joining conservatives in an arms race that shows no sign of slowing down.
Historians and legal experts who have watched Leo’s ascent struggle to name a comparable figure in American jurisprudence. “I can’t think of anybody who played a role the way he has,” said Richard Friedman, a law professor and historian at the University of Michigan.
Having reshaped the courts, Leo now has grander ambitions. Today, he sees a nation plagued with ills: “wokism” in education, “one-sided” journalism, and ideas like environmental, social and governance, or ESG, policies sweeping corporate America. A member of the Roman Catholic Church, he intends to wage a broader cultural war against a “progressive Ku Klux Klan” and “vile and immoral current-day barbarians, secularists and bigots” who demonize people of faith and move society further from its “natural order.”
Leo has the money to match his vision. In 2021, an obscure Chicago businessman put Leo in charge of a newly formed $1.6 billion trust — the single-largest known political advocacy donation in U.S. history at the time. With those funds, Leo wants to expand the Federalist Society model beyond the law to culture and politics.
Conway watched Leo become what he called a “den mother” to the justices. In liberal Washington, conservatives — even the most powerful ones — believed themselves to be misunderstood and unfairly maligned. Leo saw it as his responsibility, Conway said, to help take care of the judges even after they had made it to the highest court in the country. “There was always a concern that Scalia or Thomas would say, ‘Fuck it,’ and quit the job and go make way more money at Jones Day or somewhere else,” Conway said, referring to the powerful conservative law firm. “Part of what Leonard does is he tries to keep them happy so they stay on the job.”
On the sidelines of the Federalist Society’s annual conference, Leo made a habit of hosting a dinner at a fancy restaurant where he invited one or two justices or prominent political or legal figures (Scott Pruitt, the Oklahoma attorney general who would later serve in Trump’s cabinet, was one guest) and major donors. “With Leonard, it went both ways,” Conway said. “It made the justices happy to meet people who revered them. It made the donors happy to meet the justices and no doubt more inclined to give to Leonard’s causes.”
In 2008, as ProPublica first reported, he helped organize a weekend of salmon fishing in Alaska that included Alito and Paul Singer, the hedge fund billionaire and Leo donor. Leo invited Singer on the trip, according to ProPublica’s reporting, and Leo also asked Singer if he and Alito could fly on Singer’s plane. The Alaskan fishing lodge where the three men stayed was owned by Robin Arkley II, a California businessman and also a Leo donor. (Alito has written that the trip did not require disclosure.)
Leo has helped arrange for Scalia and Thomas to attend private donor retreats hosted by the Koch brothers dating as far back as 2007; once, Leo even interviewed Thomas at a Koch summit. The Federalist Society flew Scalia to picturesque locales like Montana and Napa Valley to speak to members. After his Napa appearance, Scalia flew to Alaska for a fishing trip on a plane owned by Arkley. Both Singer and Arkley were generous and early donors to JCN. (Arkley said in a statement: “Nothing has been more consequential in transforming the courts and building a more impactful conservative movement than the network of talented individuals and groups fostered by Leonard Leo.” Singer did not comment.)
Leo came to the aid of Thomas’ wife, Ginni, when she launched her own consulting firm, and he directed Kellyanne Conway in 2012 to pay her at least $25,000 as a subcontractor, according to The Washington Post. “No mention of Ginni, of course,” Leo instructed Conway. Leo denied that the payments had any connection to the Supreme Court’s work, and he said he obscured Ginni Thomas’ role to “protect the privacy of Justice Thomas and Ginni.”
Leo was not the only person who used faith and ideology as a bridge to the justices. Reverend Rob Schenck is a longtime evangelical Protestant minister who spent decades as a leader in the religious right. Schenck didn’t work directly with Leo, but he said he too befriended several justices, praying with them in their chambers and socializing with them outside of the court. He came to recognize the justices’ “feet of clay,” their human appetites and frailties.
“I know how much it benefited me to say to donors, ‘I was with Justice Scalia last night or last week’” or that I “‘had a lovely visit with Justice Thomas in chambers,’” Schenck said in an interview. “Anybody can try to get change at the Supreme Court by filing an amicus brief — almost anybody, let’s put it that way. But how many people can get into chambers, or better yet into a justice’s home?”
In early 2020, Leo told the news site Axios he planned to leave his day-to-day role at the Federalist Society after nearly 30 years, though he would remain on the board. Soon, Leo received all the money he would ever need to fuel his next efforts. For more than a decade, he had cultivated a relationship with a businessman named Barre Seid, who ran and owned the Chicago electronics manufacturer Tripp Lite.
Seid, who is Jewish, had long donated to conservative and libertarian causes, from George Mason University to the climate-skeptic group the Heartland Institute. Seid decided to put Leo in charge of his fortune — $1.6 billion, what was then the largest known political donation in the country’s history. Through a series of complicated transactions, Seid transferred ownership of his company to a newly created entity called Marble Freedom Trust, of which Leo was the sole trustee. (Seid did not respond to requests seeking comment.)
In late 2021, Leo took over as chairman of a “private and confidential” group called the Teneo Network. In a promotional video for the group, Leo sits on a couch in a charcoal jacket, no tie. Over upbeat music, Leo says: “I spent close to 30 years, if not more, helping to build the conservative legal movement. At some point or another, I just said to myself, ‘Well, if this can work for law, why can’t it work for lots of other areas of American culture and American life where things are really messed up right now?’” Leo went on to say his goal was to “roll back” or “crush liberal dominance.” The group had long quietly gathered conservative capitalists and media figures with politicians like Missouri Sen. Josh Hawley. Under Leo’s watch its budget soared, and new members have joined from all the corners of Leo’s network: federal and state judges, state solicitors general, a state attorney general and the leaders of RAGA and RSLC.
Other of Leo’s ventures show a willingness to embrace increasingly extreme ideas that could have sweeping consequences for American democracy. The Honest Elections Project, a direct offshoot of a group in Leo’s network, focused on election law and voting issues, was a major proponent of a legal concept known as independent state legislature theory. That theory claimed that, under the Constitution, state legislatures had the sole authority to decide the rules and outcomes of federal elections, taking the role of courts out of the equation entirely. If the theory prevailed, experts said, it could have given partisan state legislators the power to not only draw gerrymandered maps but potentially subvert the result of the next presidential election.
The Honest Elections Project filed an amicus brief when a case about the theory reached the Supreme Court. (The Supreme Court ultimately ruled against an expansive reading of the theory but did not entirely rule it out in the future.) Leo defended the Honest Elections Project, saying that “in all of its programming” it “seeks to make it easy to vote and hard to cheat. That’s a laudable goal.”
Leo’s own rhetoric has grown more extreme. Late last year, he accepted an award from the Catholic Information Center previously given out to Scalia and Princeton scholar Robert George. Rather than strike a celebratory tone, he reminded his audience of Catholicism’s darkest days in history starting with the Siege of Vienna by the Ottomans in the 17th century. Today, he continued, Catholicism remained under threat from what he called “vile and immoral current-day barbarians, secularists and bigots” who he calls “the progressive Ku Klux Klan.” These opponents, he said, “are not just uninformed or unchurched. They are often deeply wounded people whom the devil can easily take advantage of.” And after Dobbs, these barbarians were “conducting a coordinated and large-scale campaign to drive us from the communities they want to dominate.”
As Leo enters his fifth decade of activism, he has become too big to ignore. Liberal opposition research groups with their own anonymous donors have launched campaigns to expose his influence and his funders; one group even projected an image of Leo’s face onto the building that houses the Federalist Society’s headquarters in Washington. In August, Politico reported that the District of Columbia’s attorney general was investigating Leo for possibly enriching himself through his network of tax-exempt nonprofit groups. A lawyer for Leo has denied any wrongdoing and said Leo will not cooperate with the probe. In response to ProPublica’s reporting about Leo’s role in connecting donors with Supreme Court justices, Senate Judiciary Committee Chairman Dick Durbin, D-Ill., and Sen. Sheldon Whitehouse, D-R.I., demanded information from Leo, Paul Singer and Rob Arkley about gifts and travel provided to justices. A lawyer for Leo responded that he would not cooperate, writing that “this targeted inquiry is motivated primarily, if not entirely, by a dislike for Mr. Leo’s expressive activities.”
Through it all, Leo has remained defiant. His vision goes beyond a judiciary stocked with Federalist Society conservatives. It is of a country guided by higher principles. “That’s not theocracy,” he recently told a conservative Christian website. “That’s just natural law. That’s just the natural order of things. It’s how we and the world are wired.”
Bottom line—Leo wants to turn the US into a Catholic theocracy.