The i The inside story of how Leonard Leo built a machine that remade the American legal system — and what he plans to do next.
THE PARTY GUESTS who arrived on the evening of June 23, 2022, at the Tudor-style mansion on the coast of Maine were a special group in a special place enjoying a special time. The attendees included some two dozen federal and state judges — a gathering that required U.S. marshals with earpieces to stand watch while a Coast Guard boat idled in a nearby cove.
Caterers served guests Pol Roger reserve, Winston Churchill’s favorite Champagne, a fitting choice for a group of conservative legal luminaries who had much to celebrate. The Supreme Court’s most recent term had delivered a series of huge victories with the possibility of a crowning one still to come. The decadeslong campaign to overturn Roe v. Wade, which a leaked draft opinion had said was “egregiously wrong from the start,” could come to fruition within days, if not hours.
Over dinner courses paired with wines chosen by the former food and beverage director of the Trump International Hotel in Washington, D.C., the 70 or so attendees jockeyed for a word with the man who had done as much as anyone to make this moment possible: their host, Leonard Leo.
Short and thick-bodied, dressed in a bespoke suit and round, owlish glasses, Leo looked like a character from an Agatha Christie mystery. Unlike the judges in attendance, Leo had never served a day on the bench. Unlike the other lawyers, he had never argued a case in court. He had never held elected office or run a law school. On paper, he was less important than almost all of his guests.
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.
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