How a Trump adviser manipulates free speech to advance his causes and ‘hurt his adversaries’

Towards the end of July Leonard Leo, architect of the rightwing takeover of the American judiciary, emerged from his vacation retreat in Maine to write an opinion piece for the local newspaper, the Bangor Daily News, headlined: “When is free speech protected?”

Leo, 58, is the low-profile, deceptively nondescript co-chair of the conservative legal group Federalist Society. That he turned his hand to this topic was in itself no surprise – he has long presented himself as a champion of the first amendment, with its guarantees of freedom of religion, speech, press and peaceable assembly.

“Free speech is essential for a free society,” he wrote. “As such, it is something that I have defended and will continue to defend, and I have always accepted that there will be objections and opposition to the work I do.”

But a couple of eye-catching, and seemingly incongruous, events have led to speculation that his commitment to free speech might be more complicated than he professes, and more self serving. If all American citizens are equal in front of this vital element of the US constitution, could it be that some people – notably Leo himself – are more equal than others?

The first of the two events took place in the bailiwick of the Bangor Daily News, in Maine, where Leo has a $3m waterfront estate on an elite island community in Northeast Harbor. On 20 July, Jane Mayer of the New Yorker reported on a new lawsuit that had been brought by a 23-year-old local resident for wrongful arrest.

Eli Durand-McDonnell, a landscaper, was part of a group of progressive activists who staged a series of peaceful protests outside Leo’s home. They were angry about his role in securing a rightwing supermajority on the US supreme court, and the evisceration of fundamental rights that flowed from that.

Leo had proposed to Donald Trump the names of all three of the justices appointed by the former president: Neil Gorsuch, Brett Kavanaugh and Amy Coney Barrett. As such, he played a critical role in the court’s overturning of the right to an abortion in June 2022.

Leo isn’t named as a defendant in the civil lawsuit, which accuses two local police officers of making an illegal and retaliatory arrest of Durand-McDonnell during one of the protests on 31 July 2022, a month after the devastating abortion ruling. But it does claim that the arrest was made “at the direct behest of Leo, a powerful and wealthy conservative political activist who has used millions of dollars as political speech to influence American politics and courts”.

The complaint discloses that the head of Leo’s private security detail contacted the Bar Harbor police while one of the protests was occurring outside his home, singling out Durand-McDonnell for supposedly harassing the Federalist Society chief and his family. Leo told a police officer who turned up at the scene: “I think it’s time for us to press some charges,” adding, “I really feel like this is a guy who’s got to be in jail someday, and sooner rather than later.”

In his Bangor Daily News op-ed, Leo said that before the protest Durand-McDonnell had yelled at his wife and daughter that they should burn in hell. “I don’t take reporting someone to the police lightly. But, as a husband and a father, neither can I take harassment of my wife and children lightly,” he wrote.

Durand-McDonnell saw the event differently. He denies harassing anyone, insisting that all his actions were political protest that is protected by the first amendment.

“I think this case sums it up perfectly,” he told the New Yorker. “The rules don’t apply to Leonard Leo … If he doesn’t agree with what someone else says, it’s no longer free speech.”

The second event burst into public view five days after Mayer’s New Yorker article. On 25 July, Leo wrote a letter through his lawyer to two leading Democratic US senators on the judiciary committee, Dick Durbin and Sheldon Whitehouse.

The senators wanted Leo to answer a series of questions about his ties to the supreme court justices as part of an ethics investigation they were conducting. Leo has long been a figure of interest for Congress, given his outsized influence on US politics and the courts.

He is credited as being both brains and brawn behind the long campaign to steer the federal judiciary sharply to the right. He helped place at least 200 judges on the federal bench, and then went on to transform the nation’s most powerful court.

“Leo has been the central driving figure of the conservative movement’s decades-long effort to reshape the supreme court’s composition and outcomes,” said Alex Aronson, a judicial accountability advocate and Whitehouse’s former chief counsel in the US senate. “He has his fingerprints on every one of the six Republican-appointed justices who are now on the court.”

Leo has also become a focus of intense public scrutiny after he was handed a $1.6bn fund to spend on boosting conservative causes. He now controls a pot of money that represents possibly the largest single donation to a political nonprofit in US history.

Leo’s name has repeatedly popped up in the wave of ethics scandals that has washed over the supreme court this year. In April, when ProPublica published its blockbuster expose of Justice Clarence Thomas’s chummy relations with the Texas real estate magnate Harlan Crow, there was Leo depicted in a painting that hangs at Crow’s luxury lakeside resort in upstate New York sitting alongside Crow and Thomas in amicable conversation.

A month later the Washington Post revealed that Leo had arranged for Thomas’s wife, the pro-Trump extremist Ginni Thomas, to be paid tens of thousands of dollars for consulting. “No mention of Ginni, of course,” Leo instructed the polling firm that supplied the cash.

A month after that, ProPublica unleashed another blockbuster that disclosed the luxury fishing trip in Alaska that Justice Samuel Alito went on in 2008 bankrolled by the hedge fund billionaire Paul Singer. There was Leo again, pictured with Singer and Alito holding king salmon they had caught.

Leo, who assisted Alito in his 2006 confirmation to the supreme court, had a hand in arranging the trip. That included asking Singer for seats on his private jet which the justice failed to disclose as he was legally required to do.

In the wake of these ethically dubious bombshells, Durbin and Whitehouse decided to conduct their own inquiry as part of congressional oversight. They wanted to know from Leo further details of the Alaska fishing trip and what transportation, lodging and gifts he had provided to any of the justices.

In his response, Leo turned once more to the first amendment. This time, though, he made the opposite argument: unlike the Maine protester who he said had no free speech right to harass him, Leo said he had an absolute first amendment right that protected his dealings and communications with Alito and the other justices.

“Mr Leo is entitled by the First Amendment to engage in public advocacy, associate with others who share his views, and express opinions on important matters of public concern,” his lawyer wrote. Leo declined to cooperate with Congress.

One of the striking aspects of Leo’s use of the first amendment in these two events is that in both instances he sets himself up as the victim of harassment. In Maine, he was “harassed” by Durand-McDonnell who in Leo’s view went beyond civil speech and therefore forfeited his first amendment protections.

In the letter to Congress, Leo presents himself as being “harassed” by the senators for exercising his first amendment rights to interact with the supreme court justices in any way they liked.

This glaring duality – the same harassment claim played both ways with the first amendment – has caught the attention of Leo’s critics. “He’s a free speech champion when it means forcing his radical agenda on everyday Americans and refusing to cooperate with Congress,” said Kyle Herrig, senior adviser to the government corruption watchdog Accountable.US. “But he does an about-face as soon as the free speech is directed at him.”

The Guardian reached out to Leo to invite his reaction to this criticism, but he did not respond.

Aronson called the arguments laid out in Leo’s letter refusing to cooperate with Congress “comically absurd”. “What Leo argued here is that Congress lacks authority to investigate the supreme court. That position has no basis in the constitution or in any precedent.”

Aronson said that this was nothing new: Leo and the network of dark money groups he coordinates, along with the conservative justices of the supreme court he helped into power, have long massaged the first amendment for political gain. “The first amendment has been a particular target of political manipulation by Leo and the conservative legal movement across a range of subjects,” he said.

In 2010 the supreme court ruling Citizens United used free speech as a way to open the door to massive spending in elections by corporate donors. Then in 2021, in a much less noticed ruling, Americans for Prosperity v Bonta, the rightwing justices effectively created a new first amendment right to keep the identity of big donors secret.

In the judicial term that ended in June, the six conservative justices again turned to the first amendment – this time to unleash open discrimination against LGBTQ+ communities in the name of protected speech. In a dissent, Sonia Sotomayor warned that business services could now be denied any vulnerable group, such as interracial couples or parents with disabled children, all in the name of “free speech”.

Now, in the latest iteration of the use of the argument by the right, Trump himself is leaning on a free speech defense in response to this week’s indictment over his attempts to overthrow the 2020 election.

Stand back from all this, and Aronson believes we are witnessing the unfolding of Leo’s judicial revolution. “Highly influential political actors are developing incomparable sway over the judiciary after decades of coordinated investment,” he said.

“The law is becoming manipulable to advance their ends. And hurt their adversaries.”