Leonard Leo: Man in the Middle, Part I

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 that he appears. And like a spider, he prefers to stay hidden.

I first wrote about him in February 2021, in a piece called “Leo the Cancer.” Leo, who I described as “a dandier George Constanza, or if The Penguin worked at Jones Day,” has, I explained,

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.

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, which I have attempted to map out here.

Note: Leo has so many connections that it became unwieldy to confine them to a single dispatch. In today’s installment, I will cover the judges, non-profiteers, lawyers, media members, and titled Europeans. Part Two will focus on the billionaire donors, the politicians, and the religious contacts.

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Judges

Antonin Scalia (1936-2016), Clarence Thomas (b. 1948), John Roberts (b. 1955), Sam Alito (b. 1950)
Supreme Court justices

Leonard Leo worshiped at the altar of Scalia, has been close with Thomas for decades and regards him as a sort of godfather, and worked maniacally to secure the confirmations of Roberts and Alito. Thomas and Alito, in particular, he remains tight with, as recent reporting by ProPublica has made clear.

Regarding Alito, the author of the dreadful Dobbs decision: in his 2018 Daily Beast piece on Leo, Jay Michelson points out that “few people had heard of [Alito] before Leo first promoted him.” Alas, we’ve all heard of that sneeringly arrogant dickhead now.

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Arthur Raymond Randolph (b. 1943)
Judge, Court of Appeals for the District of Columbia Circuit (senior status)

In his tenure on the D.C. Circuit, Randolph sided with Nazis over the families of Holocaust victims, lost his shit when one of his fellow judges circulated an email about a climate change seminar (which Randolph called “nonsense” and “supposedly science”), and determined that the rights guaranteed under the Constitution did not apply to prisoners at Guantanamo Bay. A young Leonard Leo began his law career as a clerk for Randolph, who, like Leo and Alito, is originally from New Jersey.

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Neil Gorsuch (b. 1967), Brett Kavanaugh (b. 1965), Amy Coney Barrett (b. 1972)
Supreme Court Justices

As Donald Trump’s “judge whisperer,” Leonard Leo had a hand in picking all three of FPOTUS’s wretched SCOTUS nominees, who need no further elaboration here.

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Non-Profiteers

Carrie Severino (b. 1977)
Judicial Crisis Network head

The former Carrie Campbell grew up in Michigan, the daughter of an oncologist and a nurse. She studied biology at Duke, linguistics at Michigan State, and law at Harvard. She is the wife of Roger Severino, another Leo lackey, whom she met in Cambridge. After a year as a clerk for Clarence Thomas—finishing school for the Leo crew—she was awarded a fellowship by the Federalist Society. The Judicial Crisis Network, the PR arm of Leo’s loose network of organizations, hired her in 2010 as its policy director. She’s been there ever since, leading, with great effectiveness, the charge against Obama’s judicial nominees, for Trump’s judicial nominees, and against the Affordable Care Act and anything to do with abortion. As Leo’s de facto PR flack, Severino’s role in the overturning of Roe—long a “dream” of hers—is impossible to overstate.

Three years ago, at the height of the pandemic, Severino was diagnosed with breast cancer. “On the eve of Election Day 2020,” the New York Times reported, “Severino was undergoing chemotherapy and steeling herself for surgery and radiation therapy.” Her medical treatment was successful, and her cancer is now in remission. Her six children did not lose their mother because of the life-saving medical treatment she received. It’s ironic that the daughter of an oncologist and beneficiary of modern healthcare would make it her life’s work to deny other women access to life-saving medical treatment. But that’s exactly what Dobbs has done.

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Neil Corkery (b. 1959), Ann Corkery (b. 1962)
Board members

The husband-and-wife team sits on the board of various Leo-aligned organizations, helps Leo manage the complex financial transactions in his network of non-profits, and, according to Michelson at the Daily Beast, were (still are?) members of Opus Dei. Michelson writes:

The Corkerys have been staff members or directors at the extreme-right Catholic League (famous for its boycotts of movies; its leader Bill Donohue said the group focuses on “public embarrassment of public figures who have earned our wrath.”); the anti-gay National Organization for Marriage (Neil served as treasurer); and Leo-affiliated organizations like the Becket Fund and the Judicial Crisis Network.

The couple also ran a now-defunct dark money group called the Wellspring Committee—one tactic Leo often employs is to shut down one dark money operation and start up a new one, with an even more obscure name—whose attorney was Cleta Mitchell, of insurrection fame. Mitchell is besties with. . .

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Ginni Thomas (b. 1957)
Political activist, SCOTUS wife

Mrs. Clarence Thomas has been in bed with Leonard Leo, metaphorically speaking, for many years. As Aaron Harris astutely points out, “With $550K from Harlan Crow, Ginni Thomas founded what may have been the very first dark money group with Leonard Leo, Liberty Central, in late 2009—weeks or months before the Citizens United ruling. Leo registered it in VA one week before CU.” As Harris says, interesting timing. Leo also covertly funneled cash to Ginni—and, by extension, Clarence—via then-pollster Kellyanne Conway, in 2012. Leonard Leo’s name has appeared in every ProPublica story so far about Supreme Court corruption. His relationship with Ginni Thomas, I imagine, is a big reason why.

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Ed Wheelan (b. 1960)
Ethics and Public Policy Center, VP/former president

A graduate of Harvard undergrad and law, Wheelan was once a clerk for, and is now a co-editor of the writings of, Antonin Scalia. The Ethics and Public Policy Center is a conservative think tank dedicated to applying “the riches of the Judeo-Christian tradition to contemporary questions of law, culture, and politics, in pursuit of America’s continued civic and cultural renewal,” whatever that means.

Reportedly, Wheelan and Brett Kavanaugh are pals. During the latter’s confirmation hearing, the former gained a measure of infamy for a Twitter thread in which he claimed, ridiculously even in the moment, that Christine Blasey Ford’s sexual assault allegations were a case of faulty memory, and that it was a classmate of Kavanaugh’s, and not Kavanaugh himself, who assaulted Blasey Ford. His thread involved photos of a house where the classmate then lived. His was an elegant, well-thought-out theory, except for the pesky fact that Blasey Ford knew both of the men in question pretty well, and thus could tell them apart. Wheelan was assisted in his rollout of the False Kavanaugh Theory by. . .

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Greg Mueller (b. 1963)
CRC Advisors president

Creative Response Concepts Public Relations, of which Mueller was the head, was the maverick PR firm responsible for Swift Boat Veterans for Truth, which had a hand in dooming the presidential campaign of John Kerry. In 2020, that agency re-formed as CRC Advisors, with a big financial boost from the 85 Fund and the Concord Fund, two Leonard Leo dark money groups. This wasn’t some charitable donation. Like most of the individuals in Leo’s inner circle, Mueller is really good at his job. The False Kavanaugh Theory was (arguably) a misfire, but over the last three decades, Mueller/CRC has done savvy, creative, and effective PR work for the Federalist Society, the Judicial Crisis Network, the aforementioned Concord Fund, Chevron, the Media Research Center, the conservative press Regnery Publishing, and any number of Republican politicians. In 1997, a conservative pollster told the Washington Post that CRC was doing “a phenomenal job at a time when a lot of people within the party feel like the congressional Republicans are failing them.” That pollster was. . .

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Kellyanne Conway (b. 1967)
Political strategist, former presidential advisor

The former Kellyanne Fitzpatrick has swum in the same Beltway waters as Leonard Leo for decades; that’s no alternative fact. As the Washington Post reported last month, in January of 2012, he directed her to “‘give’ Ginni Thomas ‘another $25K,’ the documents show. He emphasized that the paperwork should have ‘No mention of Ginni, of course.’” You don’t issue commands like that to someone you don’t completely trust.

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Will Hild III (b. 1985?)
Executive Director, Consumers’ Research

Not to be confused with Consumer Reports, Hild’s outfit is a dark money group that two months ago rolled out “Woke Alerts,” a service that informs conservatives who can’t think for themselves which companies or products to avoid on account of “wokeness.” The Center for Media and Democracy has a nice write-up on Hild, a Leonard Leo protégé:

Will Hild is the executive director of Consumers’ Research, a dark-money group that is one of the largest funders of the State Financial Officers Foundation (SFOF). Since he assumed that position in 2020, the organization has filed lawsuits against the Consumer Products Safety Commission and the Federal Communications Commission (FCC), and launched a multimillion-dollar smear campaign against BlackRock CEO Larry Fink. Consumers’ Research hosts a tracker highlighting anti-ESG legislation.

Hild previously served as deputy director of the Federalist Society’s Regulatory Transparency Project and worked at the Philanthropy Roundtable. He holds a law degree from Georgetown and a bachelor’s in political science from the University of Florida.

Two weeks ago, I’d never heard of this dude. But as Leo turns his un-woke attention away from law and towards the culture, Hild and his contemptible organization will likely play a more prominent role.

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Lawyers

Peter “Bo” Rutledge (b. 1970)
Dean, University of Georgia School of Law

Once a clerk for Clarence Thomas, Rutledge is a member of the Federalist Society and the author of Arbitration and the Constitution and co-author of International Civil Litigation in United States Courts. He was a Fulbright Professor at the University of Vienna Law School and has spoken at numerous universities abroad, including Oxford, Cambridge, the University of Mainz, Jagiellonian University, Stockholm University and the University of Oslo. He is the youngest of the five men in the painting shown in the investigative piece at ProPublica, sitting with Harlan Crow and Clarence Thomas, and at the right hand of Leonard Leo. The fifth man in the painting was . . .

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Mark Paoletta (b. 1962)
Attorney

As assistant counsel to the President in 1991, Paoletta played a big role in getting Clarence Thomas through the confirmation process—no small feat. He was general counsel to the Office of Management and Budget during the Trump Administration, working for Mick Mulvaney. He served as Ginni Thomas’s attorney during the January 6 hearings. In the infamous painting, he is in the middle, higher than the others, his legs open—a position of power.

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Media Figures

James Taranto (b. 1966)
Editorial features editor, Wall Street Journal

Knows Leo well enough to have co-edited a book with him—that book is the 2005 Free Press release Presidential Leadership: Rating the Best and the Worst in the White House, and I shudder think how Bizarro World those rankings are—and is now in charge of the op-ed page at the Wall Street Journal, where a certain corrupt Supreme Court Justice recently published a piece futilely attempting to justify his corruption.

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Montse Alvarado (b. 1991?)
President, EWTN News

Formerly the head of the Leo-backed Becket Fund, a “non-profit, public-interest legal and educational institute with a mission to protect the free expression of all faiths,” Alvarado took the Tom Wambsgans job at Eternal Word Television Network, the cable channel providing 24/7 Catholic-themed programming, in January of this year. The Catholic News Agency reports:

Having known Alvarado in their mutual defense of religious liberty as well as her media work, Cardinal Timothy Dolan of New York praised her as “a first-rate journalist, a top-notch administrator, and, just as importantly, a faithful daughter of the Church.” 

With Leo and Greg Mueller, she sits on the board of the Catholic Information Center in Washington, of which more in Part II.

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Steve Bannon
Podcast host, criminal

The “War Room” podcaster and convicted felon formed the watchdog group Reclaim New York in 2013, before his troubles with the law, with his partners Robert and Rebekah Mercer; Leo soon joined the party. Bannon also teamed with radical Catholics to take on reformist Pope Francis, and tried to set up a neo-Fascist “gladiator school” at the Regensburg castle belonging to . . .

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European Nobility

Gloria von Thurn und Taxis (b. 1960)
Dowager princess, artist, Catholic activist

The former Maria Gloria Ferdinanda Joachima Josephine Wilhelmine Huberta Gräfin von Schönburg-Glauchau is the daughter of Joachim, Count of Schönburg-Glauchau, and the Countess Beatrix Maria Valeria Thérèse Emerica Széchenyi de Sárvár-Felsővidék. She married the 11th prince of Thurn und Taxis, the hip playboy Johannes, in 1980. (The family, which acquired its fortune running the postal service for the Holy Roman Empire, features prominently in the cult classic Thomas Pynchon novel The Crying of Lot 49, but that’s neither here nor there.) She was an artist and a fashion plate known for her punk-rock style, earning her the tabloid nickname “Princess TNT.”

After her husband died in 1990, the party stopped, and she inherited his debts, which amounted to half a billion clams—real money to the rest of us, but he was worth six times that, so she was able to make good. Soon after, she had a religious experience and converted to Catholicism. This resulted in her befriending Cardinal Josef Ratzinger, who in 2005 became Pope Benedict XVI. She later bonded with Bannon over a mutual dislike of Pope Francis.

Princess Gloria came to Washington in 2019, accompanied by her friend and ally, the arch conservative theologian Cardinal Gerhard Ludwig Müller. (There is a photo of the two Europeans on that visit with Justices Alito and Kavanaugh). At a speech introducing Müller, she sung his praises by proclaiming, “The only person today that gives us clearness is Donald Trump—and Cardinal Ludwig Müller!”

And then she thanked Leonard Leo for setting up the event, because of course he did.

There is nothing to suggest that a single pfennig of the Thurn und Taxis fortune has underwritten Leonard Leo’s activities. He doesn’t need Princess Gloria’s family money; he has plenty of homegrown billionaires willing to write him fat checks, as I will discuss in the next installment. But one of the less remarked-upon problems with Citizens United pertains to national security. If dark money groups don’t have to disclose their donors, how do we know those donors are not German dowager princesses, Russian mobsters, Saudi royals, Chinese Communist Party apparatchiks, or Vatican sedevacantists?

We don’t. Only Leonard Leo knows for sure.

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Next Tuesday: Part Two.