![\"Donald](\"https:\/\/d2eehagpk5cl65.cloudfront.net\/img\/c800x450-w800-q60\/uploads\/2026\/10\/Trump-40-years-2-800x450.jpg\")
<\/picture> <\/div>\nThree 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 <\/span>told<\/span><\/a> The New York Times<\/span><\/i> 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.<\/span><\/p>\n Paul Gapp, the <\/span>Chicago Tribune<\/span><\/i>‘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.<\/span><\/p>\n Trump did not like what Gapp said. And according to Trump, Gapp had no right to his opinion. Two months after the Tribune<\/em> published Gapp’s column, Trump sued<\/a> him and the newspaper for defamation. <\/span>The complaint alleged that Gapp’s criticism of the theoretical skyscraper, which also included a <\/span>Wall Street Journal<\/span><\/i> 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.<\/span><\/p>\n U.S. District Judge Edward Weinfeld, who <\/span>dismissed<\/span><\/a> 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\u2014an urge he has found irresistible as president, especially during his current term.<\/span><\/p>\n Those vendettas frequently run into legal obstacles, as recently illustrated by Trump’s <\/span>attempt<\/span><\/a> to ban disfavored journalists from the White House. Given his strikingly poor <\/span>track record<\/span><\/a> in court, you may wonder why he bothers. His take on a defamation lawsuit he filed in 2006 provides a clue.<\/span><\/p>\n In his 2005 book <\/span>TrumpNation<\/span><\/i><\/a>, 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\u2014about $8.5 billion today. Although that lawsuit also <\/span>flopped<\/span><\/a>, Trump had no regrets. “I spent a couple of bucks on legal fees, and they spent a whole lot more,” he\u00a0<\/span>told<\/span><\/a>\u00a0<\/span>The Washington Post<\/span><\/i>\u00a0in 2016. “I did it to make [O’Brien’s] life miserable, which I’m happy about.”<\/span><\/p>\n 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 <\/span>describing<\/span><\/a> his claim that Joe Biden stole the 2020 election as “the Big Lie.” Three years later, a federal appeals court decisively <\/span>rejected<\/span><\/a> Trump’s understanding of defamation.<\/span><\/p>\n Two years ago, Trump <\/span>sued<\/span><\/a> CBS and <\/span>The<\/span><\/i> Des Moines Register<\/span><\/i>, preposterously <\/span>claiming<\/span><\/a> that their journalism\u2014a pre-election interview with Democratic presidential nominee Kamala Harris and a poll giving her a lead in Iowa, respectively\u2014amounted to consumer fraud. In the CBS case, Trump averred that he had suffered “at least” $20 billion in damages. He ultimately <\/span>extracted<\/span><\/a> 0.08 percent of that amount in a settlement, although an Iowa judge <\/span>dismissed<\/span><\/a> the lawsuit against the <\/span>Register <\/span><\/i>with prejudice in September.<\/span><\/p>\n Last August, Trump <\/span>threatened<\/span><\/a> the Center for American Progress with a $5 billion defamation lawsuit unless it retracted a <\/span>report<\/span><\/a> 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.<\/span><\/p>\n Trump, in short, is still fond of frivolous litigation. He <\/span>thinks<\/span><\/a> it is “disgusting the way the press is able to write whatever they want to write,”\u00a0and he <\/span>wants<\/span><\/a> 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.<\/span><\/p>\n 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.<\/span><\/p>\n In 1798, amid a panic about a possibly imminent war with France, Congress approved the <\/span>Sedition Act<\/span><\/a>, which\u00a0made 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.\u00a0The 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.<\/span><\/p>\n The case against Matthew Lyon, a Democratic-Republican congressman from Vermont, illustrates the Sedition Act’s broad sweep. Lyon’s purported crimes included a <\/span>letter<\/span><\/a> in <\/span>Spooner’s<\/span><\/i> Vermont Journal<\/span><\/i> 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.”<\/span><\/p>\n Lyon’s indictment, legal historian Wendell Bird notes in his 2020 book\u00a0<\/span>Criminal Dissent<\/span><\/i><\/a>,\u00a0“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.<\/span><\/p>\n 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.<\/span><\/p>\n 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.<\/span><\/p>\n In August 1862, at President Abraham Lincoln’s behest, Secretary of War Edwin Stanton responded to draft resistance with orders that <\/span>suspended<\/span><\/a> 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.”<\/span><\/p>\n 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 <\/span>writes<\/span><\/a>. “At least 350 people were arrested in the following month,” and “some of the accused had done nothing worse than bad-mouth the president.”<\/span><\/p>\n More than 4,000 civilians were <\/span>tried<\/span><\/a> by military commissions during the Civil War. Focusing on arrests of civilians in loyal states, historian Mark E. Neely Jr. <\/span>concluded<\/span><\/a> that “most had nothing to do with dissent or political opposition.” But some cases did involve <\/span>disloyal speech<\/span><\/a>, as opposed to espionage, sabotage, violence, or obstruction of troops.<\/span><\/p>\n In April 1863, Union Gen. Ambrose Burnside issued <\/span>General Order No. 38<\/span><\/a>, which authorized the arrest of people “declaring sympathies for the enemy.” The most famous target was Ohio congressman Clement Vallandigham, a Democrat who was <\/span>arrested<\/span><\/a> for publicly condemning the war as “wicked, cruel, and unnecessary,” saying it was “not being waged for the preservation of the Union” but for\u00a0“the freedom of the blacks and the enslavement of the whites.” After Vallandigham was convicted, the Supreme Court <\/span>declined<\/span><\/a> to hear his petition, saying it had “no power to review” decisions by military commissions.<\/span><\/p>\n 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 <\/span>noted<\/span><\/a> 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.<\/span><\/p>\n Something similar happened during World War I, when Congress approved the\u00a0<\/span>Espionage Act of 1917<\/span><\/a>, which made it a crime, punishable by up to 20 years in prison, to obstruct military recruitment. The\u00a0<\/span>Sedition Act of 1918<\/span><\/a>\u00a0extended 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.<\/span><\/p>\n President Woodrow Wilson’s underlings <\/span>arrested<\/span><\/a> 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\u00a0<\/span>Schenck v. United States<\/span><\/i><\/a>,\u00a0the Supreme Court unanimously upheld their Espionage Act convictions, saying such speech posed a “clear and present danger” in the context of an ongoing war. A week later, the justices applied the same reasoning in\u00a0<\/span>upholding<\/span><\/a>\u00a0the Espionage Act conviction of perennial Socialist presidential candidate Eugene V. Debs, who had been sentenced to 10 years in federal prison for criticizing the war and the Wilson administration.<\/span><\/p>\n In 1919 and 1920, Attorney General A. Mitchell Palmer oversaw a <\/span>campaign<\/span><\/a> against communists and anarchists that included thousands of arrests. Hundreds of foreign citizens who had been legally residing in the United States\u2014including Russian-born anarchist Emma Goldman, who had received a two-year prison sentence for encouraging draft resistance\u2014were deported based on their political views.<\/span><\/p>\n The repression was not limited to opponents of the war. Wilson also targeted women’s suffrage activists, who had embarrassed him by demanding that he embrace their cause. From 1917 to 1919, hundreds of White House picketers were <\/span>arrested<\/span><\/a>, ostensibly for obstructing the sidewalk, and 168 went to jail, in some cases repeatedly.<\/span><\/p>\n So far, Trump has not managed to imprison his political opponents. But not for lack of trying.<\/span><\/p>\n In November 2025, after Sen. Mark Kelly (D\u2013Ariz.) and five other Democratic members of Congress posted a <\/span>video<\/span><\/a> reminding U.S. military personnel of their duty to “refuse illegal orders,” Trump <\/span>said<\/span><\/a> they “should be ARRESTED AND PUT ON TRIAL.” He accused Kelly et al. of “SEDITIOUS BEHAVIOR AT THE HIGHEST LEVEL,” <\/span>adding<\/span><\/a> that their conduct was “punishable by DEATH!”<\/span><\/p>\n Trump’s reasoning might have passed muster in 1798, 1862, or 1918. But nowadays, such “seditious behavior” is not a crime under the U.S. Code, let alone a crime that triggers the death penalty. And as a federal judge later\u00a0<\/span>noted<\/span><\/a>, the allegedly criminal video was “unquestionably protected” by the First Amendment.\u00a0But that did not deter Jeanine Pirro, the U.S. attorney for the District of Columbia, from trying to deliver on her boss’s threat.<\/span><\/p>\n Last February, Pirro <\/span>sought<\/span><\/a> an indictment charging the legislators with felonies under a <\/span>federal law<\/span><\/a> that applies to someone who “causes or attempts to cause insubordination, disloyalty, mutiny, or refusal of duty by any member of the military or naval forces of the United States”\u2014language that resembles a provision of the 1917 Espionage Act. But the grand jury apparently was not willing to participate in Trump’s vendetta. After it unanimously <\/span>refused<\/span><\/a> to approve the indictment, Pirro <\/span>gave up<\/span><\/a>.<\/span><\/p>\n Unlike Pirro, Lindsey Halligan, the defense lawyer whom Trump appointed as the interim U.S. attorney for the Eastern District of Virginia in September 2025, had no prior prosecutorial experience. But Halligan was more successful at helping Trump. At first.<\/span><\/p>\n Halligan took office two days after Trump publicly demanded that Pam Bondi, then the attorney general, find a crime to pin on former FBI Director James Comey, long an object of the president’s ire because of his role in the “Russiagate hoax” during Trump’s first term. “We can’t delay any longer,” Trump\u00a0<\/span>told<\/span><\/a>\u00a0Bondi in a Truth Social post. “JUSTICE MUST BE SERVED, NOW!!!” The same post noted that Trump had appointed Halligan, “a really good lawyer,” to replace Erik Siebert, who had proven insufficiently keen on prosecuting Trump’s enemies, as interim U.S. attorney.<\/span><\/p>\n Halligan acted quickly, <\/span>delivering<\/span><\/a> an indictment three days after taking Siebert’s place. It <\/span>charged<\/span><\/a> Comey with lying to Congress during testimony he gave on September 30, 2020,\u00a0meaning Halligan had managed, just barely, to meet the statutory deadline for prosecuting him. But two months later, a federal judge <\/span>dismissed<\/span><\/a> the indictment after concluding that Halligan had been illegally appointed.<\/span><\/p>\n What to do? Todd Blanche, who took over the Justice Department after Bondi got the ax last March, had a solution. In April, Blanche <\/span>announced<\/span><\/a> a new indictment, this time charging Comey with publicly threatening to assassinate Trump.<\/span><\/p>\n![\"A](\"https:\/\/d2eehagpk5cl65.cloudfront.net\/img\/q60\/uploads\/2026\/10\/image-1.png\")
When Dissent Was a Crime<\/b><\/h2>\n
Trump Tries to Emulate Wilson<\/b><\/h2>\n
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