Leonard Leo, ‘Free Speech’ Guy, Had Man Arrested for Calling Him a Fascist, Per Lawsuit

A 23-year-old told Leo—the man who wrote Trump's shortlist for the Supreme Court—that he's “a fucking fascist,” and Leo called the cops.

Leonard Leo, ‘Free Speech’ Guy, Had Man Arrested for Calling Him a Fascist, Per Lawsuit
Leonard Leo and a protest near Leo’s Maine house on the Dobbs anniversary, June 24, 2022 Photo:Left: Associated Press, Right: Twitter/JaneMayerNYer (AP)

Leonard Leo, the Federalist Society co-chair who handpicked Trump’s Supreme Court nominees and loves free speech when it comes to dark money political donations, was not so supportive of the First Amendment when it came to someone criticizing him.

According to a new report from the New Yorker, Leo allegedly directed police to arrest a man who called him a “fucking fascist” in Mount Desert Island, Maine, last summer, and now the man is suing, claiming that Leo violated his First Amendment right to protest. Leo told the New Yorker via email that he “informed the police” about the protestor “because his repeated incidents of erratic and aggressive demeanor had escalated into targeting my family.”

If you’re blessed enough to have never heard of the Federalist Society, it’s a conservative legal group that basically operates as an incubator for conservative lawyers and judges. Donald Trump chose all three of his Supreme Court nominees from a FedSoc list drawn up by Leo himself, and Leo has vacationed with Justices Clarence Thomas and Samuel Alito. Leo and FedSoc love free speech for corporations, PACs, and religious people: Three of the Justices Leo said Trump should nominate recently ruled in favor of a Christian website designer who claimed that a non-discrimination law violated her free speech rights. (Trump appointee Neil Gorsuch wrote that opinion!)

Leo bought his mansion on Mount Desert Island in 2018, and residents started regularly protesting near his waterfront estate after the Supreme Court overturned Roe v. Wade last June. The “fucking fascist” incident happened on July 31, 2022, when Anna Durand, a progressive activist, and owner of a local inn, was on her way to one of those protests with her son, Eli Durand-McDonnell, 23. Durand said there are other objectionable rich people in town that she ignores, but Leo “specifically made it his life’s work to take people’s rights away.” I’ll let the New Yorker set the rest of the scene:

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 was taken away in handcuffs for disorderly conduct, and photos posted to Twitter from that day show that protestors wrote on the roadway in chalk, “free speech dies here” with a red finger pointing to Leo’s house. When Durand-McDonnel arrived at Hancock County jail, he said the booking officer was confused: “That’s all you’re in for? Whatever happened to ‘sticks and stones’?”

The local district attorney dropped the charges earlier this year saying he had more important things to deal with. But on Thursday, Durand-McDonnell filed a federal lawsuit in U.S. District Court for the District of Maine. Per the New Yorker, the suit accuses two officers of the Mount Desert and Bar Harbor Police Departments of perpetrating a “retaliatory arrest to silence Durand-McDonnell’s free speech” while acting “at the direct behest of Leo.”

The lawsuit relies on audio from the arresting officer’s camera that reveals Leo called the police on July 31. Leo then had a conversation with two officers in his study in which he claimed that Durand-McDonnell had been harassing him and his family “for weeks” and said “I think it’s time for us to press some charges,” adding “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 denied to the New Yorker that he’d harassed anyone but said he did blow kisses at Leo’s security guards.

Leo also seemed upset with the tenor of the protestors’ speech, arguing that the words themselves were harassment: “This is no longer a political protest,” he said to the police, “when they have ‘Fuck Leo’ signs…and their Twitter and Facebook posts talk about ‘Get out,’ and ‘You don’t belong here.’” The officers then arrested Durand-McDonnell, and, in so doing, the suit claims, “retaliated against Durand-McDonnell for exercising one of his most important constitutional rights and sought to chill his political speech.”

The attorney who filed the suit, Matthew Morgan, said that a disorderly-conduct charge under Maine law requires police to witness “fighting words” intended to provoke violence—shouting an expletive from a car on the way to a peaceful protest doesn’t meet the standard. “You have the head of the Federalist Society getting a guy arrested for carrying a sign in front of his house,” Morgan said. “It’s quite an irony.”

Leo added in his emailed statement: “I hope Mr. Durand gets the help he needs to properly distinguish between First Amendment speech and menacing attacks on innocent bystanders.”

Durand-McDonnell says the whole saga thus far is a microcosm of the influence that Leo and other conservative activists have on the law and civil rights. “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.”

Blowing you a non-ironic kiss, Eli.

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