First Amendment

Trump Has Been Trampling Free Speech for More Than 40 Years—and It Keeps Getting Worse

The president stands out from his modern predecessors by openly displaying his contempt for the First Amendment.

Jacob Sullum | 10.11.2026 7:00 AM

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(Illustration: Adani Samat | Photo: Album/sfgp/Aaron Schwartz/Pool via CNP/Picture Alliance/Consolidated News Photos/Newscom/Newspaper.com)

Three decades before he was first elected president, Donald Trump had big plans for a 26-acre building site near the South Street Seaport in Manhattan. "New York City deserves to have the tallest and greatest building in the world, and I would be very interested in doing it," he told The New York Times on July 30, 1984. He imagined a 150-story structure, including offices, apartments, and a hotel, that would be 1,940 feet high, surpassing Chicago's Sears Tower, then the world's tallest building, by nearly 500 feet.

Paul Gapp, the Chicago Tribune's architecture critic, did not think much of that plan. "The only remotely appealing aspect of Donald Trump's proposed 150-story Manhattan skyscraper, announced several days ago, is that it would not be done in the Fence Post Style of the 1970s," Gapp wrote. "The world's tallest tower would be one of the silliest things anyone could inflict on New York or any other city." Trump was indulging in "Guinness Book of World Records architecture," Gapp said.

Trump did not like what Gapp said. And according to Trump, Gapp had no right to his opinion. Two months after the Tribune published Gapp's column, Trump sued him and the newspaper for defamation. The complaint alleged that Gapp's criticism of the theoretical skyscraper, which also included a Wall Street Journal interview in which he called it "aesthetically lousy," had damaged Trump's reputation to the tune of $500 million, the equivalent of $1.6 billion today.

U.S. District Judge Edward Weinfeld, who dismissed Trump's lawsuit in September 1985, had little trouble recognizing that Gapp's comments were "entitled to complete immunity under the First Amendment protection" for "expressions of opinion." But far from deterring Trump, that episode was the first of his many attempts to punish people for saying things he did not like—an urge he has found irresistible as president, especially during his current term.

Those vendettas frequently run into legal obstacles, as recently illustrated by Trump's attempt to ban disfavored journalists from the White House. Given his strikingly poor track record in court, you may wonder why he bothers. His take on a defamation lawsuit he filed in 2006 provides a clue.

In his 2005 book TrumpNation, financial journalist Timothy O'Brien dared to suggest that the developer was worth less than he claimed. Trump responded by suing O'Brien and his publisher for defamation, claiming they had caused him $5 billion in damages—about $8.5 billion today. Although that lawsuit also flopped, Trump had no regrets. "I spent a couple of bucks on legal fees, and they spent a whole lot more," he told The Washington Post in 2016. "I did it to make [O'Brien's] life miserable, which I'm happy about."

Trump is still using lawsuits to make his enemies suffer. In 2022, he sued CNN, seeking $475 million in punitive damages. Trump said CNN had defamed him by describing his claim that Joe Biden stole the 2020 election as "the Big Lie." Three years later, a federal appeals court decisively rejected Trump's understanding of defamation.

Two years ago, Trump sued CBS and The Des Moines Register, preposterously claiming that their journalism—a pre-election interview with Democratic presidential nominee Kamala Harris and a poll giving her a lead in Iowa, respectively—amounted to consumer fraud. In the CBS case, Trump averred that he had suffered "at least" $20 billion in damages. He ultimately extracted 0.08 percent of that amount in a settlement, although an Iowa judge dismissed the lawsuit against the Register with prejudice in September.

Last August, Trump threatened the Center for American Progress with a $5 billion defamation lawsuit unless it retracted a report questioning the effectiveness of his National Guard deployment in the District of Columbia. As Trump sees it, even criticism of a president's policies qualifies as libel.

Trump, in short, is still fond of frivolous litigation. He thinks it is "disgusting the way the press is able to write whatever they want to write," and he wants to "open up our libel laws" so he can "win lots of money" when news outlets publish stories that are "purposely negative and horrible and false." But as president, Trump has many other weapons at his disposal, and he has used them in a way that sets him apart from his recent predecessors.

In terms of measurable consequences, Trump's weaponization of government against his political opponents pales beside what happened during the "Quasi-War" with France, the Civil War, and World War I, when dissenters went to prison. But Trump has tried to do something similar on a smaller scale, deploying the criminal justice system against his nemeses in retaliation for their constitutionally protected speech. He also has used regulatory threats, sanctions against reporters, immigration law, federal grants, and executive orders to make people think twice about crossing him. And unlike, say, President Richard Nixon, who had no compunctions about abusing his powers for political purposes but generally did so secretly, Trump has done all this openly, proudly displaying his contempt for the First Amendment.

When Dissent Was a Crime

In 1798, amid a panic about a possibly imminent war with France, Congress approved the Sedition Act, which made it a crime, punishable by a fine up to $2,000 (something like $54,000 today) and up to two years in jail, to write or publish "any false, scandalous, and malicious writing" against "the government of the United States," Congress, or the president. The Federalists who controlled Congress viewed their Democratic-Republican opponents as "Jacobins" apt to welcome French conquerors, and they saw criticism of President John Adams and his allies as an intolerable threat to order and national security.

The case against Matthew Lyon, a Democratic-Republican congressman from Vermont, illustrates the Sedition Act's broad sweep. Lyon's purported crimes included a letter in Spooner's Vermont Journal averring that Adams had forsaken "every consideration of the public welfare" in "a continual grasp for power" and "an unbounded thirst for ridiculous pomp, foolish adulation, and selfish avarice."

Lyon's indictment, legal historian Wendell Bird notes in his 2020 book Criminal Dissent, "showed how relatively mild criticism could be treated as criminal libel under the Sedition Act" and "how opinion as well as fact could send someone to prison." Lyon was convicted and sentenced to four months in jail plus a $1,000 fine.

Based on court records, Bird counted 51 Sedition Act prosecutions involving 126 defendants, including 14 newspaper editors and three politicians. That tally, he says, "shows a far more serious and determined Federalist effort to criminalize dissent and to suppress the opposition press and party" than previous accounts recognized. Nearly all the defendants were Democratic-Republicans. Bird found just one acquittal, reflecting the influence of Federalist judges who were keen to facilitate such cases.

The Sedition Act, which expired in March 1801, was largely a response to a war that never actually happened. As you might expect, real wars tend to inspire broader repression.

In August 1862, at President Abraham Lincoln's behest, Secretary of War Edwin Stanton responded to draft resistance with orders that suspended the writ of habeas corpus across the country. He authorized the arrest and military trial of anyone "engaged, by act, speech, or writing, in discouraging volunteer enlistments, or in any way giving aid and comfort to the enemy, or in any other disloyal practice against the United States."

That mandate "allowed local sheriffs and constables to decide arbitrarily who was loyal or disloyal, without even considering the administration's main goal of enforcing the draft," historian David Greenberg writes. "At least 350 people were arrested in the following month," and "some of the accused had done nothing worse than bad-mouth the president."

More than 4,000 civilians were tried by military commissions during the Civil War. Focusing on arrests of civilians in loyal states, historian Mark E. Neely Jr. concluded that "most had nothing to do with dissent or political opposition." But some cases did involve disloyal speech, as opposed to espionage, sabotage, violence, or obstruction of troops.

In April 1863, Union Gen. Ambrose Burnside issued General Order No. 38, which authorized the arrest of people "declaring sympathies for the enemy." The most famous target was Ohio congressman Clement Vallandigham, a Democrat who was arrested for publicly condemning the war as "wicked, cruel, and unnecessary," saying it was "not being waged for the preservation of the Union" but for "the freedom of the blacks and the enslavement of the whites." After Vallandigham was convicted, the Supreme Court declined to hear his petition, saying it had "no power to review" decisions by military commissions.

The Lincoln administration also shut down more than 300 newspapers, which were typically published by Democrats sympathetic to the Confederacy. This was "the greatest amount of newspaper suppression in the nation's history," journalism professor David W. Bulla noted in 2009, although he highlighted an 1863 letter from Lincoln to a general in Missouri suggesting that the president had second thoughts about the crackdown.

Something similar happened during World War I, when Congress approved the Espionage Act of 1917, which made it a crime, punishable by up to 20 years in prison, to obstruct military recruitment. The Sedition Act of 1918 extended that crime to include "any disloyal, profane, scurrilous, or abusive language" regarding "the form of government of the United States," the Constitution, or the armed forces.

President Woodrow Wilson's underlings arrested more than 2,000 people under those laws, resulting in some 1,000 convictions. The defendants included Charles Schenck and Elizabeth Baer, Socialist Party leaders who were accused of distributing anti-draft pamphlets. In the 1919 case Schenck v. United States, the Supreme Court unanimously upheld their Espionage Act convictions, saying........

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