Even an exclusive summer oasis is no refuge from the divisive partisan politics poisoning much of the country. In the fall of 2018, Leonard Leo, the powerful leader of the conservative legal group the Federalist Society, bought a lavish $3.3-million waterfront estate in Northeast Harbor, Maine, on Mount Desert Island, an area famous for its staggering beauty and equally staggering old money. Northeast Harbor’s ethos is understated and blue-blooded. Peabodys, Vanderbilts, and their latter-day incarnations sail, golf, play tennis, and host dinners at grand shingle-style houses often referred to as “cottages.” “Until recently, the only thing anyone thought about here was their backhand,” Alison Schafer, a fifth-generation summer resident, told me. “But, since Leo arrived, the town is in turmoil.”
The acrimony has been escalating since last summer, when the conservative majority on the Supreme Court, whose appointments many have ascribed to Leo’s machinations, overthrew Roe v. Wade, the fifty-year-old decision protecting women’s reproductive rights. Soon after, dozens of local protesters began appearing outside Leo’s house nearly every weekend, carrying posters decrying the corruption of the judiciary and encouraging sympathizers who drove by to honk their car horns. On July 31st, Anna Durand, a local inn owner, was on her way to one such protest with her son Eli Durand-McDonnell, a twenty-three-year-old landscaper. Durand is a longtime progressive activist in the community, and she conceded that “there are plenty of people who’ve made objectionable fortunes here” whom she deplores but ignores. But she believes Leo is uniquely deserving of condemnation because, in her view, he has “specifically made it his life’s work to take people’s rights away.” As she and her son drove down the town’s main street, she spotted Leo, who was walking with his family: “I was, like, ‘OMG—there he is!’ ” From her car, she yelled, “Leonard Leo!” He said, “Yes?” She later recalled, “I always wanted to say such a profound statement if I saw him.” But, in the moment, she said, “I just yelled, ‘You’re a fucking asshole. You’re going to Hell. Your whole family is going to Hell.’ It was so satisfying. I drove away happy.”
Before she drove off, however, Durand-McDonnell, who was in the passenger seat, chimed in. “You’re a fucking fascist,” he recalled shouting at Leo. Hours later, Durand-McDonnell was at the protest, standing with a dozen or so demonstrators on the shoulder of a public roadway in front of Leo’s property, when police arrived to arrest him. “I asked, ‘What for?’ ” Durand-McDonnell told me. “Honestly, I was so surprised. It was more that than rage or fear. I couldn’t imagine I’d done anything to get arrested.” The officers charged Durand-McDonnell with disorderly conduct and put him in handcuffs. Having done some work at a nonprofit dealing with violence prevention, he worried that an arrest record would ruin his future. As he was driven away, the other protesters, many of them older women who could recall the days before Roe, shouted at the arresting officers, “Shame! Shame! Shame!” At the Hancock County jail, according to Durand-McDonnell, the booking officer, after hearing the details of the disorderly-conduct charge, said, “That’s all you’re in for? Whatever happened to ‘sticks and stones’?”
Demonstrators protest across from Leonard Leo’s house in Northeast Harbor, Maine, on June 24th, the first anniversary of the Supreme Court’s Dobbs decision.Photograph by Jane Mayer / The New Yorker
No one is more identified with the Court’s conservative turn than Leo, and arguably no issue has been more ardently championed by the Federalist Society than the right to free expression enshrined in the First Amendment of the Constitution. Supreme Court Justices who are associated with the Federalist Society, and whose appointments Leo had promoted, have ruled in favor of the First Amendment right of religious opponents of same-sex marriage to deny some business services to couples of whom they disapprove, and of the right of rich political donors to spend unlimited amounts of money on campaigns as a form of speech. “I think the left misunderstands what we define as rights in our country sometimes, because frankly, those are defined by the Bill of Rights,” Leo said, in an interview this week with the conservative news site Maine Wire. “Most of these rights that we’re talking about in the Bill of Rights are freedom from government oppression, freedom from government interference, they are political and civil rights.”
Today, however, a civil lawsuit was filed in the U.S. District Court for the District of Maine that turns the tables on the Federalist Society’s co-chairman. Eli Durand-McDonnell is alleging that Leo instigated his wrongful arrest—for calling Leo “a fucking fascist.” The suit, a four-count complaint, doesn’t name Leo as a defendant. But it accuses two officers of the Bar Harbor and Mount Desert Police Departments of perpetrating a “retaliatory arrest to silence Durand-McDonnell’s free speech” while acting “at the direct behest of Leo,” whom the suit describes as “a powerful and wealthy conservative political activist who has used millions of dollars as political speech to influence American politics and courts.” As evidence, the suit draws on a recording taken from the arresting officer’s police camera, documenting that Leo called the police on July 31st. Soon after, the audio reveals that, in a private consultation in his study, the Federalist Society co-chairman told the officers that Durand-McDonnell had been harassing him and his family, and that “I really feel like this is a guy who’s gonna be in jail someday, and sooner rather than later.” Leo gave the police an account that differed in several respects from Durand-McDonnell’s. He said that, earlier that day, as he was walking with his wife and eleven-year-old daughter toward the center of town, Durand-McDonnell had shouted at him while driving past him in a car, calling him a “fucking asshole.” Leo said that he recognized Durand-McDonnell, who, he claimed, had been “harassing” him and his family “for weeks.” He told the officers, “I think it’s time for us to press some charges.” He continued, “I have to be honest with you . . . the man looks unstable. He looks hateful. He looks really angry, and he’s really starting to concern me.” (Durand-McDonnell acknowledges that he had blown kisses at Leo’s security guards, but denies harassing anyone.) Leo went on, “If he wants to put a bullet between my two eyes, fine, let him do it, O.K.? But I can’t have him dealing with my family that way. My wife was distraught.” He acknowledged that the issue of protected speech was difficult, and he could see it both ways. But he argued that the behavior of the protesters had gone beyond politics, to personal harassment. “This is no longer a political protest,” he asserted, “when they have ‘Fuck Leo’ signs . . . and their Twitter and Facebook posts talk about ‘Get out,’ and ‘You don’t belong here.’ ”
Matthew Morgan, Durand-McDonnell’s attorney, argued that shouting an expletive from a car fell well beneath the threshold needed for such a disorderly-conduct charge, which, under Maine law, requires a law-enforcement officer to witness “fighting words” likely to provoke physical violence. As Morgan put it in a phone interview, “You have the head of the Federalist Society getting a guy arrested for carrying a sign in front of his house. It’s quite an irony.” Soon after conferring with Leo in his library, according to the complaint, the two police officers arrested Durand-McDonnell. In their doing so, the complaint asserts, “the officers’ collective actions retaliated against Durand-McDonnell for exercising one of his most important constitutional rights and sought to chill his political speech.”
That day, Durand-McDonnell was released on bail. And last May, prior to trial, the local district attorney dropped the charges against Durand-McDonnell, explaining that he had more important matters to deal with. (The police officers didn’t respond to requests for comment.) In an e-mail, Leo ascribed the district attorney’s decision to drop the charges to a “lack of resources.” He also stressed that he had “relied on the police to figure out how best to resolve this.” And he emphasized his contention that “Mr. Durand went out of his way to harass my wife and young daughter as we were walking along the street, accosting them directly after addressing me and then standing outside our house to be there when we returned. I informed the police because his repeated incidents of erratic and aggressive demeanor had escalated into targeting my family.” And, he added, “I hope Mr. Durand gets the help he needs to properly distinguish between First Amendment speech and menacing attacks on innocent bystanders.” Eli Durand-McDonnell, for his part, offered some pointed, if less off-color, words than those he used last summer. “I think this case sums it up perfectly,” he said recently, sitting on a public bench along Northeast Harbor’s main street, a few yards from the scene of the alleged crime. “The rules don’t apply to Leonard Leo. He can use this insane amount of money and influence and be a big shot, and throw his weight around. And, if he doesn’t agree with what someone else says, it’s no longer free speech.” ♦
