Leonard Leo and the Unholy Trinity (with Tom Carter)
How the reactionary legal activist, radical Catholic zealot & dark money maestro built alliances to capture the Court and impose his extremist agenda on America
On these pages, I’ve written extensively about Leonard Leo. In February of 2021—three full years ago—I wrote a piece called “Leo the Cancer,” an introduction to a dark money maestro his BFF Clarence Thomas once called, without hyperbole, the third most powerful man in the country. Citing great investigative journalism by Jay Michelson at the Daily Beast, ProPublica, Heidi Przybyla at Politico, and Nina Burleigh at the New Republic, I’ve also detailed how Leonard Leo personally cashed in on his legal activism; how Leonard Leo wangled $1.6 billion—billion with a B—out of the reclusive nonagenarian electronics magnate Barre Said, and the malefic effect that will have on our democracy; and how many powerful people exist in the network he’s built over the last three decades of activism.
Here is a synopsis of who Leo is, for those unfamiliar:
He’s one of the most powerful individuals in the country. His spiderweb of connections is extensive. But most Americans, including many working in Washington, have never heard of him.
Occupying the center of an intricate web of political, legal, religious, and business connections, Leonard Leo is the quintessential Man in the Middle, a veritable dark-money spider. Like a spider, he is patient, painstaking, relentless, and much more powerful than he appears. And like a spider, he prefers to stay hidden. . .
When I began researching that piece, I didn’t know much about the guy beyond his silly, comic-book-villain name. I was surprised to discover that he was, like me, a middle-class product of Catholic upbringing and Italian descent who graduated from a public high school in New Jersey—not at all the well-heeled, oenophilic Master of the Universe he has become. He’s also much younger than I expected; born in 1965, he’s solidly Gen X—only seven years older than Yours Truly.
Yet Leonard Leo, somehow, is the individual most responsible for stripping away federal abortion rights. (The anniversary of the odious Dobbs decision was this past weekend.) As his admiring chum Ed Wheelan presciently wrote in 2016, “No one has been more dedicated to the enterprise of building a Supreme Court that will overturn Roe v. Wade than the Federalist Society’s Leonard Leo.”
As Politico reported—and as I outlined on these pages three months ago—Leo has been rewarded handsomely for his troubles. “I personally don’t believe that Leonard is motivated by greed,” Steven Calabresi, who founded the Federalist Society with Leo and still runs the organization, told Politico. “I think Leonard is motivated by ideology and ideas. I do think he likes to live a high-rolling lifestyle, but I don’t think he’s in the business because of the money.”
To be fair, Leo does spread that money around. He endows more organizations than I can succinctly list here. Friends like Ginni Thomas get a taste. He brings his SCOTUS cronies on lavish fishing trips with his billionaire backers. And yet Payoff Lenny—as I call him—has amassed a fortune for himself, and spends that fortune lavishly: on tailored suits, palatial vacation homes in Maine, and bottles of wine that cost more that what most Americans pay for a month’s rent.
Jesus liked wine, yes, and Jesus hung out with fishermen, sure, but I’m not sure the Son of God would approve of Leo’s stockpile of dirty loot—although his fellow Knights of Malta don’t seem to mind. Money washes away a lot of sins, as anyone familiar with the history of the Catholic Church well knows.
And so the rich and powerful Leonard Leo presides spider-like over Washington, moving chess pieces across the great board, raising unfathomably vast sums of money, and cultivating his extensive network.
Tom Carter knows more about Leonard Leo than anyone not in the Federal Society co-founder’s inner circle. Tom worked in Washington for years, in journalism and then in PR. For three years, he handled media relations at USCIRF, the U.S. Commission on International Religious Freedom, where his boss was—you guessed it—Leonard Leo. He soon realized that Leo was a zealot, whose ideas were incompatible with, among other things, religious freedom.
Over the subsequent decade and a half, Tom became a dedicated Leo watcher. He reads every article about him. He’s developed his own network of sources. And he warns everyone who will listen about how powerful Leonard Leo is—and how dangerous to our democracy. I’m grateful to Tom for coming on the PREVAIL podcast and spilling the Leonard Leo tea:
Whenever I write about Leo, someone on social media will invariably bring up Jeff Sharlet and The Family, as if Leonard Leo and his crew are the same thing. They are not. Leo & Co. are radical Catholics; The Family are Protestants. Yes, both are Christians, but being Christian didn’t stop Catholics and Protestants from fighting each other in Europe for centuries. Conflating the two mischaracterizes who Leo is and what he ultimately wants.
Carter has a smart way of breaking down the relationship between 1) Leo and his radical Catholic cohorts; 2) Evangelical Christians; and 3) Mammon-worshipping rightwing billionaires. He calls it the “Unholy Trinity.” (Another name might be “The Devil’s Triangle,” if we felt like hat-tipping Leonard Leo’s penultimate SCOTUS appointment, the odious Brett Kavanaugh.)
“Herman Hesse, like 1945, 46, somewhere in there, was given the Nobel Prize for Literature. So, you know, in the 60s, when I was in college, he was one of the people, one of the authors everybody read. And he wrote books like Siddhartha and Steppenwolf and so on,” Carter tells me. “One of the books he wrote was called Magister Ludi, The Glass Bead Game. And it was about all these elites in an ivory tower who played, like, eight-dimensional chess. Everybody had a chess board in their room, and when a physicist made a move on his chess board, the oboe player in another room could respond with his musical background, and a scientist could respond with his background. So there was like this eight, you know, eight, 10, 12 dimensional chess going on. Leonard is a little bit like that. To understand what he’s doing is at least three levels or four levels of chess.”
Leonard Leo is the Bobby Fischer, moving the pawns and knights and bishops into attack formation. He exploits the wants and needs of both the Evangelicals and the mega-rich libertarians to get his way.
“The libertarian billionaires want something,” Carter explains. “In 1980, one of the Koch brothers ran for vice president, got less than 2% of the vote—on a platform which is very much today’s MAGA platform. So it was not a popular platform. It’s never been a popular platform, but they knew [they didn’t] have the votes. So the Kochs, the Scaifes, the Uihleins, Paul Singer, Harlan Crow, Barre Said, all of these guys have different individual wants, but in general, what it boils down to is they want lower taxes on their multi-billion-dollar companies, and they want no federal regulation.”
Basically, these soulless gajillionaires, many of whom inherited their wealth, would rather spend hundreds of millions if not billions of dollars in lobbying efforts—funding all manner of vile rightwing fuckery to make sure their hard-inherited cash doesn’t help the less fortunate—than pay their fair share. Leo knows all of this. He is a master of exploiting the contempt these selfish jerks have for the taxman to get them to fund his various enterprises. When it comes to siphoning away their fortunes, he’s like a catfisher extraordinaire, a veritable Nigerian prince. Although, unlike the catfisher or the Nigerian prince, Leonard Leo delivers the goods.
The problem is, most non-billionaires would prefer that the grotesquely wealthy would, you know, pay their fucking taxes. Income inequality in this country is disgusting. The Lorenz curve is bulging like Leonard Leo’s waistline after a steak dinner at Morton’s. So American voters were not going to race to the polls to support lowering taxes for the brothers Koch. This unpopularity posed a problem, back in the 80s.
“So where do we get the votes? Where do we get the votes?” Carter explains. “Well, Paul Weyrich, a very devout, hardcore Catholic, who has said the more people vote, the less people will like our positions,” had a planning sesh with Jerry Falwell—“a top Catholic meeting with a very, very top Evangelical.”
This was after the Supreme Court decided the Bob Jones University case in 1983. “Bob Jones University was a Christian university that practiced racism because the Bible tells us so,” Carter explains. “So they did not allow interracial marriage until racial dating, all of that sort of stuff. Somebody brought it to the Supreme Court and the Supreme Court said, ‘Well, yeah, you can do that if you want, that’s your religious freedom, but you don’t get government subsidies. You don’t get a tax break. You don’t get money from, you know, the common pot.’”
Since Brown v. Board of Education, Christian private schools had popped up in the South as a way to bypass the ruling and keep their schools segregated. The Bob Jones ruling threatened all of that. “They recognized that their tax exempt status was at risk with this Bob Jones University thing,” Carter explains. “So what do we do? We can’t sell racism. That’s not going to sell in the, in the, you know, late 1970s, early 1980s. ‘What do we want? What do we want? I know. Let’s get behind abortion. Let’s become anti-abortionists.’ So this was a political marriage between Paul Weyrich—conservative Catholics—and Jerry Falwell—conservative Evangelical Christians. And that’s how the anti-abortion movement really came about. It wasn’t Roe that started it. It was these two guys basically in a backroom deal.”
And that’s how the second prong of the Unholy Trinity fits into the picture. Falwell’s community, Carter explains, “are the votes. Those are the infantry. Those are the door knockers, the Evangelical Christian nationalists, which we’ve read so much about. And Katherine Stewart’s book, Power Worshippers, if you haven’t read it, I strongly recommend you read it. Also Sarah Posner’s book. Also, Jeff Sharlet has done some great stuff on The Family and on C Street. All of this is Protestant oriented.”
“At the same time, Leonard Leo and his Catholic cabal was beavering away in Washington trying to rig the judicial system. It’s been said if you want to create a fascist society, the first thing you do is get the judges, and that’s what Leonard was doing,” Carter tells me. “It’s what I call the Unholy Trinity. You’ve got the libertarian billionaires; you’ve got the Christian nationalist foot soldiers, the infantry; and you’ve got the extreme Catholic—Leonard Leo—cabal, driving the tanks, or to use a different analogy, kicking the goals. They’re the ones that are getting stuff done. They are putting the scores on the scoreboard.”
This concerted effort to force a reactionary agenda on our government has been going on for decades. The Unholy Trinity has been waging a Christofascist libertarian holy war against the rest of us—and we haven’t even realized it. One minute, Weyrich is plotting with Falwell; the next minute, Leonard Leo has installed five Justices on the Supreme Court, and is bosom pals with a sixth. The Trump Administration was honeycombed with Leo’s ideological allies, particularly in the last days of his term. And now, enriched by $1.6 billion in libertarian billionaire loot, Leo has enough money to fund his extremist activities in perpetuity. (Will he also use that money to help the sick and needy, I wonder, as actual Catholicism demands?)
“There’s been a lot of stories, ink, books, articles on Christian nationalism and how there is no separation of church and state, and we want Jesus at the top of the heap, our version of Republican Jesus at the top of the heap. There’s been very little on the [radical] Catholics, and they’re actually the ones that are doing a lot of the lifting,” Carter says. The goal is to not just eliminate the separation of church and state, but to elevate the church to the dominant position—where it was in the Middle Ages, when the Pope crowned the emperors.
The thought leaders of this extremist Catholic movement are quite open about the necessity of force to get their way. “Force will be required,” Carter says, paraphrasing the thought process of these leaders. “Force is going to be needed, because not everybody is going to want to do what we say we want to want done. So if you’re Jewish, or Catholic [but don’t] believe in integralism, or an atheist, or anything else, you automatically become a second-class or third-class citizen in this Christofascist world. Think about the Spanish Inquisition or, more recently, think about Franco’s Spain or, today, Orbán’s Hungary. These are autocratic societies run according to religious principles, whoever happens to be at the top of the heap.”
If this unholy power grab is complete—which, if Trump wins re-election, it will be—it ain’t going to be pretty for the rest of us. Which is to say: most of us.
Carter sums up the situation succinctly—and ominously: “They’re bringing the Inquisition.”
LISTEN TO THE PODCAST
SEASON 7 PREMIERE: All About Leonard Leo, the Reactionary Legal Activist, Radical Catholic Zealot & Dark Money Maestro Who Captured the Supreme Court (with Tom Carter)
Tom Carter worked in Washington for years, in journalism and then in PR. For three years, he handled media relations at USCIRF, the U.S. Commission on International Religious Freedom, where his boss was one Leonard Leo, a key figure in the conservative legal movement and the capture of SCOTUS. The conversation explores the background, influence, and agenda of Leonard Leo; his management style, his use of dark money, his involvement with the Federalist Society and other organizations; his connections to Clarence Thomas and other influential figures; and the extreme radical Catholic religious beliefs that animate his opposition to abortion and LGBTQ rights. The conversation also delves into the potential ramifications of Leo's actions, his expansion into the media and entertainment industry, and the future of his influence. Overall, it highlights the danger and harm caused by Leo's agenda. Plus: Cole Porter lives!
Takeaways:
Leonard Leo is a key figure in the conservative legal movement and has significant influence behind the scenes.
Leo's use of dark money and his web of organizations have allowed him to boost the conservative legal movement and shape the Supreme Court.
His radical Catholic beliefs and agenda drive his opposition to abortion and LGBTQ rights.
Leo's expansion into the media and entertainment industry through the Teneo Society raises concerns about his potential influence in these areas.
The real-world ramifications of Leo's actions include the erosion of democratic principles and the harm caused to marginalized communities.
00:00: Episode introduction
10:43: Beginning of the interview
22:37: Leonard Leo’s Influence and Methods
25:28: Dark Money and Leonard Leo’s Organizations
36:55: Relationship between Leonard Leo and Clarence Thomas
47:19: The Libertarian Billionaires and Leonard Leo’s Agenda
52:19: The Distinction between Radical Catholicism and Mainstream Catholicism
1:06:26: Leo’s networks
1:17:27: The Virtually Unlimited Financial Resources of Leonard Leo
1:32:16: The Danger and Harm Caused by Leonard Leo's Actions
Follow Tom:
https://www.threads.net/@thcarter123
Extremist all over the globe that make us cringe and we think thank god we are in America- nothing like this could ever happen here, when in reality, we are closer to the handmaids tale than ever before. I have said for years it’s time to remove all tax free status from churches. Separation of church and state is and should be top priority for us etc etc etc
JFC
I'm glad that the Vatican's role in the ongoing destruction of our democracy is finally being recognized. I learned early on about the underbelly of the Vatican as a former seminarian at a Benedictine monastery. The Vatican MO being used by LL has been honed by centuries of the same in nearly every nation on Earth. Some of those nations like Ireland have finally begun to resist Vatican influence. Others like Hungary still have a long way to go. Maybe with investigative reports like yours and others the U.S. will also begin to resist Vatican influence. Thank you.