Greg Olear is a novelist and journalist who writes a blog called PREVAIL. The following post appeared there. I post only part of it. If you want to see his complete list of Leonard Leo’s claque, open the link and continue reading. This is part one of a two-part report.

Greg Olear writes:

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 Churchwell 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.

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.

To learn more about Leonard Leo’s circle, open the link and keep reading.