No former president has challenged the limits of freedom of expression like Donald Trump. Often overbearing and at times downright rude, Trump has tested the boundaries of what can be called political speech. Here’s the latest.

The most significant challenge to the First Amendment came during Trump’s penalty phase trial for fraud, based on his over-valuing his properties in New York to obtain favorable loan rates. Trump tussled there with the presiding judge, Arthur Engoron and, oddly, the law clerk seated beside him on the bench.

Already upset over what he felt was the clerk’s overinvolvement in the trial (including whispering in the judge’s ear) Trump seized on a vanilla selfie photo of the clerk with Democratic Senator Charles Schumer to taunt her with the phrase “Schumer's girlfriend” and insinuate as a Democrat the clerk was inherently biased against Trump.

In the way things work in 2023, these fifth grade-level slurs plus a few Trump complaints about Engoron himself being biased morphed into “threats,” somehow. Engoron went as far as to suggest that Trump was sending attack messages to his MAGA army (“targeting”), and lives were in danger.

In retaliation, Engoron slapped a gag order on Trump, later extended to his attorneys as well. The order prohibited Trump from commenting on the trial, out loud, in the press, or on social media, and specifically said the law clerk was off-limits. Trump paid little attention to the order and was fined twice for a total of $15,000. Trump called Engoron an “extremely hostile” judge. His lawyers said there was evidence of “tangible and overwhelming” bias. Trump’s lawyers then filed a lawsuit against Engoron challenging his gag order as a violation of the First Amendment.

Lawyers for Engoron argued he and his staff received hundreds of antisemitic calls and letters. They blamed Trump’s comments about Engoron and the clerk for amplifying his supporters’ anger toward them and said the clerk is “playing Whack-A-Mole now trying to block her phone number.” 

“It’s not that Mr. Trump has directly issued threats to the staff and Judge Engoron, it’s that what he’s said has led his constituents” to make threats, the lawyers argued, comparing the potential effect to the January 6 riot and a violent attack on Nancy Pelosi’s husband. 

“That is not political speech. That is threatening behavior and it should be stopped,” Engoron's lawyers argued.

The initial appeals forum which heard the case disagreed, particularly about the part saying what Trump was engaged in was not political speech. Judge David Friedman of the state’s intermediate appeals court issued a temporary stay suspending the Engoron gag order and allowing the former president to speak freely about court staff while the longer appeals process played out. Friedman questioned “Engoron’s authority to police what Trump says outside the courtroom. He also disputed the trial judge’s contention that restricting the 2024 Republican front-runner’s speech was necessary or the right remedy to protect his staff’s safety.”

Engoron’s gag order, once stayed, was reimposed pending a full hearing by an appeals court but no matter, the point had been made.

Another gag attempt was also struck down last month, after the judge overseeing Trump’s Washington J6 case briefly paused a gag order she had imposed on him. Trump reacted to this three times in three days, calling Special Counsel Jack Smith “deranged.” Twice he weighed in about the deposition testimony of his former chief of staff, Mark Meadows, who could end up a witness at the trial.

These moves prompted Smith’s team to ask the judge, Tanya Chutkan, to reinstate the gag order. She put the order back in place, though it has been frozen again as a federal appeals court considers whether Judge Chutkan properly imposed it in the first place. That suspension left Trump temporarily free of all of the gag orders placed on him.

Long term, a federal appeals court panel appeared poised to significantly narrow the gag order imposed against Donald Trump by Chutkan. The D.C. Circuit Court of Appeals panel raised concerns the order—which bars Trump from criticizing witnesses, prosecutors, and courthouse staff—created murky restrictions stifling the former president’s right to push back against his detractors, particularly in the heat of the campaign.

What at first seems novel—it happened mostly on social media!—and so very Trump—the insults, the elementary school–quality teasing—was in fact at the core of what the First Amendment is all about. Political speech is among the most protected forms of speech, moreso political speech criticizing the government. In fact not novel at all, Trump was engaged in the most basic form of expression designed to be protected by the First Amendment.

Engoron, standing in for King George here, played the role of evil government perfectly. He chose to use the power of government to stop Trump (who claims the trial is political persecution in the first place) from criticizing the government, in the guise of his court, and then doubled down by extending the order to Trump’s lawyers, and then triple-downed the whole mess saying the gag applied 24/7 to those named. This was all way beyond the limited point of a gag order, whose proper use is almost always to shield important information from a jury to not prejudice a case. A gag order should enhance democracy by protecting the right to a trial by jury, not run roughshod over it silencing the political speech of someone on trial.

The hardest thing sometimes to accept about the First Amendment is it often protects speech you don't like made by people you don’t like, in this case Trump, who is presumed guilty by some half of the electorate. This idea is captured in the quote “I disapprove of what you say, but I will defend to the death your right to say it,” often attributed to Voltaire and apparently missing from both Engoron’s and most undergraduates’ education.

Those who bleat that support for Israel or support for Palestine has no place on campus fall squarely into the same narrow box as Engoron, wanting to block speech which personally threatens them but does not rise to the level of threat established by the Supreme Court, or offends them, somehow believing the First Amendment does not protect “hate speech.” While speech might be offensive, or even feel threatening, to some people, to others “it is an expression of a political opinion, an unfiltered reaction to a recent event, or an attempt to rally support for a cause. The freedom to share provocative ideas and spark robust debate about political issues is essential to democracy, social justice, and progress.”

That’s exactly what Trump is doing when allowed, criticizing his trials and their participants in real time via press conferences and especially social media, all protected by the First Amendment.