By Greg Olear | 26 February 2021
WHAT LEONARD LEO wants you to know about Leonard Leo, first and foremost, is that he is a Knight of Malta. The Sovereign Military Order of Malta (SMOM) is a lay Catholic order that claims descent from the Knights Hospitaller, founded in Jerusalem in 1099, at the end of the First Crusade. It’s an extremely selective group. Of the 1.2 billion Catholics in the world, only 13,000 are Knights of Malta—although most of them don’t go around bragging about it.
Leo, I’m told, is very proud of this honor. First, because it demonstrates just how radically Catholic his radical Catholicism runs. And second, because it speaks to his importance. SMOM membership is the sort of status symbol that eluded him, growing up middle-class in the suburbs of New Jersey, where his high school classmates derisively nicknamed him “Moneybags.” His mother and step-father weren’t blue bloods. He wasn’t some wealthy boarding school kid. Poor guy had to make due with Cornell instead of Harvard or Yale. He was a nobody.
The Conservative Supreme Court Justices Are Inferior Judges /1
The Federalist Society..has reared a generation of phony originalists..who subscribe to a philosophy that is hostile to the advancement of social &economic progress in the country. https://t.co/vpiq6NjNbv
— Dennis S Brotman 🇺🇸 #DemCast #DemCastGA (@DenbrotS) February 2, 2022
But look at him now! Leonard Leo, 56, has made himself one of the most powerful figures in the United States. He’s put five—count ‘em, five!—justices on the Supreme Court: Amy Coney Barrett, Brett Kavanaugh, Neil Gorsuch, Sam Alito, and John Roberts. A sixth, Clarence Thomas, is one of his closest friends. And, perhaps most impressively, he quietly led the 2016 crusade to deny Merrick Garland a hearing, when Barack Obama nominated the highly-regarded jurist to replace the late Antonin Scalia (another of Leo’s pals). In the lower courts, he’s been even busier. He’s installed so many judges on so many courts, it makes you wonder if he really is the instrument of God’s will he believes himself to be. I mean, there are only three branches of government. One of those three—arguably the most important one—is Leonard Leo’s domain.
You wouldn’t know it to look at him. Leonard Leo is a short, foppish, pear-shaped man, in wire-rimmed glasses and pricey suits. Think a dandier George Constanza, or if The Penguin worked at Jones Day. As Jeffrey Toobin wrote in the 2017 New Yorker profile (that is now framed in Leo’s office):
Leo is at ease in the role of impresario. His grandfather was a vice-president of Brooks Brothers, and he instilled in young Leonard a taste for the bella figura. Leo wears tailored suits, often with contrasting waistcoats, and a double-length gold fob attached to a 1935 train conductor’s pocket watch. (“The most accurate watch in the United States until the fifties,” he said.) In lieu of office meetings, Leo prefers to chat over breakfast (just bacon, no eggs) at the Hay-Adams Hotel, across from the White House. As his friend Boyden Gray, the White House counsel under George H. W. Bush, puts it, “He knows the best restaurants in every major city in the world, and the best wines. He has a wide-ranging, inquiring mind, and he can and will talk about any subject under the sun.”
A gold fob? A fucking pocket watch? Several times in the article, we are told what an oenophile Leo is, a wine connoisseur ne plus ultra. I’m told he has his own little room in the wine cellar at Morton’s—the steakhouse’s best vintages aren’t good enough for his refined, Rothschildian palate. (One assumes that he shares with the Paul Giamatti character in Sideways a near-homicidal contempt for merlot.)
Reading Toobin’s profile—which, again, Leo was so proud of he had framed in his office—the guy strikes me as a pretentious bore, socially and intellectually insecure, desperate for people to find him extraordinary. And while I may be biased, I’m not the only one who shares this opinion. A former senior executive at one of the many entities Leo controls once remarked: “Leonard always thinks he’s the smartest person in the room. He very rarely is.”
That tracks. The smartest person in the room wouldn’t be so inflexible in his adherence to the Holy Trinity of fundamentalist Catholic political dogma: No birth control, no LGBTQ rights, no choice. The smartest person in the room would question why the church advocating for those retrograde policies is the same one that provided cover for nests of serial pedophiles…for centuries. The smartest person in the room would wonder if inveterate child molester apologists possess the requisite moral standing to denounce gays, Lesbians, and trans individuals, or to force teenage rape victims to carry their fetuses to term. Although Toobin’s New Yorker profile was widely considered a “Valentine” (or, more colorfully, a “blow job”)—a puff piece, basically—the subject of said profile is clearly not the smartest person in the room:
According to Leo, the vast majority of abortions are a consequence of voluntary, consensual sexual encounters, an opinion that influences his view of the procedure. “We can have a debate about abortion,” he told me. “It’s a very simple one for me. It’s an act of force. It’s a threat to human life. It’s just that simple.”
In the light of Leo’s perspective, the possibility that he would put forward a Supreme Court nominee who would turn out to support abortion rights seems nonexistent. Roberts and Alito have voted against reproductive rights; so, in all likelihood, will Gorsuch. As Edward Whelan, a prominent conservative legal activist and blogger, wrote recently, “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.”
Where to begin? The smartest person in the room would know that in the “debate about abortion,” such as it is, the only “act of force” involves the State forcing a woman to see through a pregnancy she does not want—one that may have begun against her will. (“Pro-life” is a euphemism for “pro-patriarchal authoritarian.”) The “threat to human life,” meanwhile, is the threat to the life of the mother that is inherently posed by any pregnancy. The smartest person in the room would grasp that a staunchly anti-choice government would put women in constant danger, at risk even of death, every time they have intercourse. The smartest person in the room would not think “voluntary, consensual sexual encounters” comprised a heinous sin, because he happened to read that in Deuteronomy or Leviticus. The smartest person in the room would understand that a woman’s right to choose allows for individual morality. It couldn’t be simpler: if Leonard Leo does not wish to have an abortion, Leonard Leo is free to not do so.
Alas, Leo is not the smartest person in the room—to the detriment of all American women.
The strain of radical Catholicism practiced by Leo and his ilk bears little resemblance to the Catholic Church in my own New Jersey hometown, where I was confirmed, or the one I encountered among the joyful Jesuits at Georgetown University, where I went to school. As I understand it, the Church is about helping those less fortunate. That’s supposed to be the primary focus. Plenty of Catholic charities, and plenty of good Catholics, understand this and behave accordingly.
I fail to understand how the less fortunate are helped by encouraging discrimination against the LGBTQ community—which for most of American history has been marginalized, harassed, picked on, beaten up, and, sometimes, executed. Or by railing against the use of condoms, which prevent the spread of HIV. Or by publicly shaming the pregnant teenager as she makes her terrified way to Planned Parenthood. As I see it, those things are self-evidently loathsome.
But Leo’s is a dour, zero-sum faith—pure, inflexible, unswerving. Less inquisition, more Inquisition. And this is no act. He really believes this crap. When I asked if Leo’s faith was sincere, Tom Carter, who was communications director at USCIRF from 2009-2012, when Leo was the de facto chief, told me: “He believes he’s on a mission from God.” That mission is to mold the judicial branch to his liking, and in so doing, to do away with Roe and protections for the LGBTQ community.
Leo is widely known as the executive vice president of the Federalist Society.
But behind the scenes, he is the maestro of a network of interlocking nonprofits and other initiatives to sway lawmakers by generating public support for conservative judges. https://t.co/4dUEXeBHSU
— The Washington Post (@washingtonpost) May 21, 2019
Understand: there are plenty of American Catholics who are pro-choice and pro-LGBTQ rights. President Biden, to name one. Justice Sonia Sotomayor, to name another. But Leo doesn’t just want any old Catholic on the high court. If so, he would have been jumping for joy about Sotomayor’s selection. (Yes, at the moment, incredibly, seven of the nine SCOTUS justices are Catholic.) What Leo wants are radical Catholics—the Church’s answer to Evangelical Christians, Chabad-Lubavitch Jews, and fundamentalist Muslims.
Because this strain of radical Catholicism lacks a proper name, it is harder for non-Catholics to make the distinction. This also makes it easy for its critics to be accused of being prejudiced against Catholics—just as critics of Israeli prime minister Bibi Netanyahu, a crook, are routinely denounced by his apologists as anti-Semites. William Donohue, longtime president of the Catholic League, wrote a letter to the editor of the New York Times in 2019 accusing Carl Hulse, that paper’s chief Washington correspondent, of “anti-Catholic bias” for daring to suggest, on a panel with another journalist, that there is a “real Catholic underground that is influencing [the court] in an outsized way”— as if Leonard Leo didn’t exist, as if the names of Donohue’s Board of Directors were not all in the guy’s Rolodex.
Although “two percent of the population is Jewish,” Donohue added, “and a third of the high court is Jewish, no one ever complains about having too many Jews on the Supreme Court.” The obvious difference is that the “too many Jews” on the Court are not beholden to an obdurate religious doctrine that, if applied the Leonard Leo way, would compel them to oppose choice and LGBTQ rights. Indeed, the main reason Leo wants these judges on the court, as he makes no bones about, is because of this opposition. This is Leo’s jihad. He wants to foist his extremist religious beliefs on all of us, to annihilate the firewall between Church and State, to impose a medieval legal system that mirrors his radical Catholic faith—call it “Mari’a Law.”
I should add here that Leo’s view of Islam seems to be more eleventh century than twenty-first. In the wake of 9/11, the U.S. Commission on International Religious Freedom, the aforementioned USCIRF, a federal agency that was controlled by Leo, led the opposition to the “Ground Zero Mosque”—despite this opposition being in direct conflict with its mission. (A key organizer of the rally against the mosque, incidentally, was GOP fundraising maven and insurrection enthusiast Virginia “Ginni” Lamp Thomas, Clarence’s wife). Around that time, USCIRF was the subject of an EEOC complaint. Safiya Ghori-Ahmad, an attorney with a graduate degree in international development whom the agency passed over, subsequently filed a lawsuit charging anti-Muslim discrimination. As the Daily Beast reported in 2017:
In early 2010, after Ghori-Ahmad’s original complaint was filed, staff and former commissioners told the Washington Post the organization was “rife, behind-the-scenes, with ideology and tribalism, with commissioners focusing on pet projects that are often based on their own religious background.” In particular, staffers said, “an anti-Muslim bias runs through the commission’s work,” charges Leo denied.
The Justice Department’s nominee to run the civil rights division has made a career out of defending big corporations against employment discrimination charges.https://t.co/vqATF4vpR0
— Public Citizen (@Public_Citizen) March 1, 2018
Even the mighty Leonard Leo takes it on the chin sometimes.
So how does he do it? How does he wield so much power? Networking. Like an invasive cancer, Leonard Leo has metastasized from the Federalist Society to the broader conservative legal community. He knows anyone and everyone, from John Roberts to Mick Mulvaney to Ed Whelan to Seamus Hasson to Nina Shea to the sommelier at Morton’s who pours out the vino. Despite being a generation younger, he was good friends with the late Antonin Scalia and remains tight with Clarence Thomas. (Perhaps Leo, whose dad died when he was five, regards these powerful men as father figures.) He delights in pulling the marionette strings. “He likes to place people,” Carter told me.
But it’s the financial networking that moves the needle. Leo sits like a giant spider at the center of a complicated web of non-profits and PACs and 501-whatevers: The Federalist Society, which identifies, develops, and grooms future conservative judges. The Judicial Crisis Network, the PR arm of the operation. The Becket Fund, a legal outfit that does pro bono work for religious freedom cases. The Freedom and Opportunity Fund, which helped bankroll the Brett Kavanaugh nomination hoo-ha. Reclaim New York, a charity Leo set up in 2013 with Rebekah Mercer and Steve Bannon. The Council for National Policy, the Christian coalition group. And God knows how many others.
A conservative activist’s behind-the-scenes campaign to remake the nation’s courts https://t.co/yCAe5qKClj
— #CaliBernication (@brooklynnygirl) May 8, 2022
Between 2014 and 2017 alone, they collected more than $250 million in such donations, sometimes known as “dark money,” according to a Post analysis of the most recent tax filings available. The money was used in part to support conservative policies and judges, through advertising and through funding for groups whose executives appeared as television pundits.
The groups in Leo’s network often work in concert and are linked to Leo and one another by finances, shared board members, phone numbers, addresses, back-office support and other operational details, according to tax filings, incorporation records, other documents and interviews.
That’s a quarter of a billion dollars in dark money donations—an almost unfathomable pile of cash. More than a little of that dark money wound up in his pocket. At the time of the Brett Kavanaugh nomination process, Leonard Leo reportedly paid off the mortgage on his own home in McLean, Virginia, and also scooped up a $3.3 million luxury estate on the Maine coast. (You know, like Jesus would do.) He paid almost a million bucks less than the appraised value of the home, which was sold to him by the estate of the late CEO of the chemical company W.R. Grace, J. Peter Grace—a fellow Knight of Malta.
The rest of that vast pool of dough sloshes around from one dark money org to the next, where it can best be deployed. Leo plants op-eds in newspapers, and he buys ads, and he hires PR outfits to do marketing campaigns, and he lobbies, and he does it in such a way that no one can see the radical Catholic Oz behind the curtain, with his gold fob and his decanter of Château Lafite.
But what if Leonard Leo isn’t the éminence grise he thinks he is? What if he’s the one being played?
* * *
The words “Opus Dei” immediately call to mind that insipid Da Vinci Code novel. If you managed to avoid reading the book, perhaps you saw the film adaptation, in which Tom Hanks is chased around Europe by a self-flagellating albino monk (played by the lead actor from WandaVision). Both book and movie are beyond parody, not least in their treatment of Opus Dei. As Anthony Lane notes, in his deliciously arch review of the film, “the Catholic organization [is] so intensely secretive that its American headquarters are tucked away in a seventeen-story building on Lexington Avenue.”
And yet, as ridiculous as The Da Vinci Code is, perhaps Dan Brown was onto something. It cannot be a coincidence that so many movers and shakers in the Washington legal community are connected to a radical brand of Catholicism that is more Urban II than John XXIII.
Along with former Attorney General Bill Barr, Leonard Leo served on the board of the Catholic Information Center, the Opus Dei stronghold on K Street in Washington, a few blocks from the White House. As such, he must have been influenced by the former head of that same Catholic Information Center, Father C. John McCloskey, an Opus Dei priest. McCloskey was singlehandedly responsible for recruiting a number of powerful Washington insiders to…well, if not Opus Dei proper, then something decidedly un-American. This is from a piece Charles P. Pierce wrote for the Boston Globe in 2003, about a group he termed “The Crusaders”:
There is a glow to the priest when he talks…He is talking about a futuristic essay he wrote that rosily describes the aftermath of a “relatively bloodless” civil war that resulted in a Catholic Church purified of all dissent and the religious dismemberment of the United States of America.
“There’s two questions there,” says the Rev. C. John McCloskey 3d, smiling…“One is, Do I think it would be better that way? No. Do I think it’s possible? Do I think it’s possible for someone who believes in the sanctity of marriage, the sanctity of life, the sanctity of family, over a period of time to choose to survive with people who think it’s OK to kill women and children or for—quote—homosexual couples to exist and be recognized?
“No, I don’t think that’s possible,” he says. “I don’t know how it’s going to work itself out, but I know it’s not possible, and my hope and prayer is that it does not end in violence. But, unfortunately, in the past, these types of things have tended to end this way.
“If American Catholics feel that’s troubling, let them. I don’t feel it’s troubling at all.”
— Charles P. Pierce (@CharlesPPierce) January 8, 2019
- Leo’s chums Antonin Scalia and Clarence Thomas
- Thomas’s wife, Ginni Thomas
- Louis Freeh, the shady former FBI Director
- the late conservative columnist Robert Novak
- Sam Brownback, the hapless former governor of Kansas
- Lawrence Kudlow, Trump’s former economic adviser
- Robert Hanssen, the FBI officer who was a KGB double agent
- Bill Barr
Leo was in his thirties when Pierce wrote that article, a Beltway neophyte, but he was already on the varsity team. In addition to the surviving members of the McCloskey group, his current circle of devout Catholics includes:
- SCOTUS justices John Roberts, Sam Alito, Neil Gorsuch, Brett Kavanaugh, and Amy Coney Barrett
- former White House Counsel Pat Cipollone
- Trump Homeland Security attorney Ken Cuccinelli
- Roger Severino (who while director of the HHS Office of Civil Rights authored some despicably anti-LGBTQ policies)
- Roger’s wife, Carrie Severino, head of the Judicial Crisis Network and Leo’s most trusted lieutenant
- Mick Mulvaney, former White House Chief of Staff
- Don McGahn, former White House Counsel, who stayed on the job as long as he did to facilitate the appointment of Leo-approved judges
- George Conway & Kellyanne Conway
Let me be clear: my first inclination, when I see the words “Opus Dei” and a list of notables, is to dismiss the whole thing as conspiracy-theory poppycock. I don’t know how many of these people are actually members of that prelature, and it really doesn’t matter. Call it what you like, but those individuals really are all connected, and really were influenced by the hateful, authoritarian thinking of Father McCloskey. Read those names again. Whether this is Opus Dei proper or something less formal, that is a fantastic amount of power concentrated in a very small circle of like-minded people.
Whatever eschatological hocus-pocus McCloskey may have subjected these individuals to, none of them seem like exemplary human beings to me—including McCloskey himself. The priest was removed from his position at the Catholic Information Center when he was accused of sexual misconduct by a woman involved with the Center—not the first time he was booted out of a plum job. Opus Dei paid almost a million bucks to settle the case, and insists that the former priestly powerbroker now “suffers from advanced Alzheimer’s…[and] has not had any pastoral assignments for a number of years and is no longer able to celebrate Mass, even privately.” The point is, the moral leader of Leonard Leo’s little group is a handsy man of the cloth who cost Opus Dei $977,000 because he couldn’t keep his mitts off a parishioner, and who in the aftermath of the scandal wound up banished from public life.
Leo and his pals are proponents of what Bill Barr, in his controversial 2019 speech at Notre Dame, called “the traditional moral order,” which is a euphemism for “hatred of the LGBTQ community, atheists, agnostics, Muslims, immigrants, and women.”
Now that US Attorney General William Barr has stepped down, it's a good time to remind people that he is a far-right theocrat who was on the board of directors of an Opus Dei front group – and it's insane that he was in charge of the DOJ in the first placehttps://t.co/g9h0RJhidD
— Benjamin Norton (@BenjaminNorton) December 15, 2020
But is it a moral order, though? A moral order that tolerates pedophiles? What’s really going on here?
Radical Catholics hate two things above all else: abortion and homosexuality. Morality debates aside, to staunchly and categorically oppose either one is to deny reality. If abortion is criminalized, abortions will still take place—in back alleys, illegally, by fly-by-night abortionists who only work for cash. Likewise, the criminalization of gay and Lesbian sex will not stop gays and Lesbians from hooking up—it will just drive the liaisons underground.
And maybe, just maybe, that’s the real objective.
Before Roe, abortions were one of the many illicit services on offer by crime syndicates. The mob took a cut of the fee, and, more importantly, knew who was getting secret abortions—and who the fathers were. The abortion racket, in other words, was a means to collect both money and dirt.
Sodomy, to use the grotesque legal term, has been decriminalized for two generations, but men having secret rendezvous with other men is still used as kompromat. Off the top of my head, I can name three current Republican Senators, a former Republican governor, a former Democratic governor, and the businessman father of a member of Trump’s inner circle who are rumored to dabble covertly in gay sex. How much more power would a potential blackmailer have over these people if man-on-man action was expressly illegal?
And who, you ask, collects dirt on prominent individuals, for the purpose of coercion and blackmail? Creatures of the underworld: crooks running rackets, and spooks working assets.
Take a look at the McCloskey list again. There are so many spies! Bill Barr, the son of an OSS agent, was himself in the CIA, and behaves like an asset for a foreign intelligence service. Robert Hanssen—whose brother-in-law was Barr’s speechwriter—worked for the KGB. Louis Freeh, head of the FBI when Hanssen was busted, has connections to foreign intelligence services, and is closely aligned with Rudy Giuliani, whose tentacles extend to Turkey, Romania, and Ukraine. Robert Novak deliberately outed a CIA agent. Not everyone is involved in espionage, of course, but there was a lot of foreign intelligence activity going on among members of Father McCloskey’s original group—and that doesn’t even count the Vatican, which boasts one of the oldest intelligence service going. Certainly their activities were, and remain, shrouded in secrecy—if Opus Dei operated out in the open, after all, a crappy novel like The Da Vinci Code would not have sold so many copies.
Two more names to consider: Steve Bannon, a Catholic, who, 1) worked with Leo in the Reclaim New York charity, 2) teamed with radical Catholics to take on reformist Pope Francis, and 3) tried to set up a neo-Fascist “gladiator school” in Rome, has ties to Chinese intelligence. And while there is no clear connection between Leonard Leo and mercenary CEO and Trump ally Erik Prince—with his alleged ties to Emirati, Israeli, and Chinese intelligence—both of these enormously powerful and influential men are radical Catholics.
Could it be that the push to criminalize abortion and homosexuality is intended to make the job of the foreign intelligence services easier? Could it be that the hardline views of “true believers” like Leonard Leo and his Torquemada besties are being manipulated to advance that agenda? Could it be that spies are exploiting the fact that a desperately insecure, status-conscious, nouveau riche sycophant who is emphatically not the smartest person in the room believes that he is?
It’s an interesting hypothesis, for sure. But let’s take them at their word. McCloskey spoke of a “relatively bloodless” civil war, because it’s “not possible” for people like him to peacefully coexist with the LGBTQ community. Barr seeks a “traditional moral order.” Leo, as Jay Michaelson succinctly explains in The Daily Beast, believes that “most of the New Deal and administrative state are unconstitutional, that corporations have free speech and free religion rights, that women and LGBT people are not ‘protected classes’ under constitutional law, and that there is no right to privacy implied by the due process clause of the Constitution (i.e., banning abortion, contraception, and gay marriage are entirely constitutional).” These are men who abhor the Equality Act, which passed the House yesterday.
Someone check on the Federalist Society-likely planning a victory party to celebrate their decades long goal to undo Roe. I believe they also have gay marriage & contraception on their agenda. They want everyone to live by their rigid religious beliefs. https://t.co/TZDudtlVcQ
— Jayme Ruimveld (@jaymeruimveld) May 9, 2022
The thing is, those are unpopular positions, reviled by a healthy majority of Americans. Given the demographic trends in the United States, the only way “The Crusaders” can bring the country back to the pre-New Deal era is to establish a dictatorship—a radical Catholic caliphate. Leonard Leo and his buddies are clearly okay with that. The Opus Dei prelature, remember, has its origins in Fascist Spain. The Roman Catholic Church is very much a top-down organization—what the Pope says goes. The late J. Peter Grace, the head of the American Knights of Malta, whose Maine compound Leo now owns, was involved in Operation Paperclip, and was therefore okay with Nazis. Steve Bannon wants to destroy the American administrative state. By eradicating the barrier between Church and State, Leo seeks the same outcome. Ultimately, what these men want is, to put it mildly, inconsistent with democracy. That makes them particularly dangerous.
One final note about Leonard Leo. He and his wife, Sally, walk the “no contraception” walk. The couple has seven children. Their oldest daughter, Margaret, was born with spinal bifida. She died in 2007, just 14 years old, a tragedy which affected Leo profoundly. Margaret Leo, it appears, was genuinely a special person—a force of enormous strength and hope, so much so that after her death, strangers prayed to her, as if she were a saint…and their prayers were, miraculously, answered. (Attested miracles, please note, are a prerequisite for sainthood.) Clarence Thomas keeps drawings she made on his desk. There was a quality about her that approached holiness.
The daughter may well have been a saint. The father is anything but. On the contrary, Leonard Leo is a demon who has taken possession of the body politic. Send for the exorcist. Cast him out.
Note: Thanks to Lincoln’s Bible, Anne Loo, and Tom Carter. Also: new version added the Conways to the list.
 I spent an hour trying to figure out which town in central Jersey he’s from, and the name of his high school—to no avail. UPDATE: A reader reports that Leo attended Monroe Township (public) High School.
 I was told of this comment by a source who worked in the same entity, and who asked to remain anonymous.
Reprinted with permission from the author.
Greg Olear is an American novelist, journalist, and author.
20/ Greg is the author of DIRTY RUBLES: AN INTRODUCTION TO TRUMP RUSSIA, as well as 2 novels. All can be found on Amazon.
PREVAIL podcast can be found on Apple Podcasts, or wherever you get your shows: https://t.co/n8YLdazcbM
And you can (& must) follow him on Twitter @gregolear
— LB 🇺🇦🌻 (@LincolnsBible) July 8, 2021
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