Sure, a president can sue the press. But can he win?

Once upon a time, in 1913, a small-town newspaper published a story that said a former American president had a drinking problem. That president, Teddy Roosevelt, sued the paper and won. His award from the jury: 6 cents.

This was the last time a U.S. president sued a media outlet for libel and won. Even filing such a lawsuit has been rare throughout U.S. history, until now.

In his most recent slew of lawsuits against the press, President Donald Trump filed a $10 billion defamation case on Friday, July 18, against The Wall Street Journal. In a clash of titans, Trump named his former ally, conservative media tycoon Rupert Murdoch, as well as two Journal reporters and the Journal’s parent companies, Dow Jones and News Corp.

“I look forward to getting Rupert Murdoch to testify in my lawsuit against him and his ‘pile of garbage’ newspaper, the WSJ,” Trump wrote Friday on Truth Social. “That will be an interesting experience!!!” 

Trump claimed he wants to make it easier to successfully sue press organizations, which would likely require an overturn of the Supreme Court’s landmark First Amendment case from 1964.

Can he? The jury’s still out.

The SCOTUS ruling that changed it all 

The now-famous 1964 case, New York Times Co. v. Sullivan, granted journalists in the United States some of the world’s strongest legal protections, paving the way for how defamation suits would proceed.

The case began with a lawsuit filed by L.B. Sullivan, the public safety commissioner in Montgomery, Alabama, who said he had been defamed by a full-page ad in The Times that criticized his city’s police officers for their conduct during civil-rights demonstrations.

In the 9-0 decision that reversed a lower court’s ruling, Justice William Brennan wrote that the case was reviewed “against the background of a profound national commitment to the principle that debate on public issues should be uninhibited, robust, and wide-open, and that it may well include vehement, caustic, and sometimes unpleasantly sharp attacks on government and public officials.” 

The First Amendment of the United States Constitution ensures press freedoms, protecting journalists from government interference and censorship.

“Congress shall make no law… abridging the freedom of speech, or of the press,” the First Amendment says. 

The role of the media is to serve as a de facto Fourth Estate, which holds accountable the three branches of government. The unanimous Sullivan decision held that the First Amendment’s free speech protections necessarily curtail the ability of public figures to sue for defamation. 

“Without New York Times v. Sullivan, it is questionable whether the press could have done as much as it has to penetrate the power and secrecy of modern government, or to confront the public with the realities of policy issues,” the late Pulitzer-Prize winning legal journalist Anthony Lewis wrote in his 1991 book, “Make No Law: The Sullivan Case and the First Amendment.

“The ultimate beneficiary,” Lewis wrote, “was not the press but the public.”

That notion still holds true today, according to Jeffrey Robbins, an attorney who has represented both media and public figures in defamation cases. 

“The First Amendment allows for the free exchange of ideas, freedom of speech,” Robbins told Straight Arrow News. “Freedom of speech is precious in the existence of a democracy.” 

“It allows the exchange of views, even if it’s vitriolic,” Robbins added.  “Sullivan allows room for the freedom to be mistaken, to get the facts wrong, to say things incorrectly … because the alternative would be to choke free expression.” 

While Sullivan gave the press more freedom, it established a legal framework and precedent that makes it tougher for plaintiffs — especially public figures — to successfully sue the press for defamation. The burden of proof falls on the public figure.  

“Here in the United States, generally — there are some funky state statues in various places — the very first thing the plaintiff has to prove is that the statement is false,” Robbins said. “In the U.K., for instance, the defendant has to prove the truth of their statement.”

Additionally, the public figure must prove that the media outlet published the statement with “actual malice.” 

“The Supreme Court took a very notable stance,” said David Enrich, a journalist and author who wrote “Murder the Truth: Fear, the First Amendment, and a Secret Campaign to Protect the Powerful.”

“They ruled that to be consistent with the First Amendment,” Enrich said, “public officials like L.B. Sullivan going forward needed to prove not only that they’d been defamed and the facts were wrong … but also that whoever published those facts had done so deliberately, either knowing the facts were wrong or with reckless disregard.”

The reception

Since 1964, many courts have cited the Sullivan precedent in First Amendment cases. People across the political spectrum applauded the Sullivan ruling, saying it ensured the rights of journalists and a free press. 

But Americans have lower rates of trust in the media today than they did half a century ago. In 1972, 68% of Americans said they had either a great deal or a fair amount of trust in mass media, according to Gallup polls from the time. By 2024, Gallup found the share had eroded to 31%. 

“When Walter Cronkite and Huntley and Brinkley were on air, there was a lot more in place for fact checking, for accountability and ethics,” said Hans von Spakovsky, a senior legal fellow at The Heritage Foundation, a conservative think tank. 

With the advent of new media such as social media and the polarization of American media outlets, von Spakovsky said, some of the heightened standards Americans had come to expect from journalists have fallen away – or at least appeared to. 

Some question Sullivan and the power dynamics it assumes.

“Courts have expanded who is considered a public person,” von Spakovsky told SAN. “Because they’re mentioned in a news story, they’re a public figure. … It’s really important people take another look at what this [Sullivan] case did. … If you’re a public person, you have to prove the media knew it was a lie when they published.”

Robbins pointed to another argument for overturning Sullivan, which centers on the shifts in technology and media ownership since the First Amendment’s passage. 

“When it was enacted, we were talking about John Peter Zenger and the printing press,” Robbins said. “We are now talking about conglomerates – multi-billion-dollar corporations that have massive, massive power. An argument for lessening the Sullivan standard is that we’re not talking about printing presses anymore. These aren’t mom-and-pop operations. We’re talking about unbelievably large corporate interests.”

Trump or his business have filed 24 media or defamation suits, including 20 since he announced his first presidential campaign in 2015, according to Axios. Trump has also alluded to wanting to overturn Sullivan. He has some well-positioned allies: Supreme Court Justices Clarence Thomas and Neil Gorsuch have both shown support for overturning the precedent. 

Is this an intimidation strategy?

While most presidents choose not to file lawsuits against the press, it’s not unusual for U.S. presidents to be in conflict with journalists over their First Amendment rights.

John Adams used the Sedition Act to jail reporters; Richard Nixon kept an enemies list, which included reporters; Barack Obama’s administration prosecuted whistleblowers under the Espionage Act in the name of national security; and Joe Biden’s administration pressured social media companies to censor certain language.

But suing journalists and threatening to overturn Sullivan has ignited ire from critics.

“The administration is making no bones about its desire to cow people,” Robbins told SAN. “Law firms, nonprofits, universities, publications – we’re in the midst of a reign of terror. And it’s not melodramatic to call it that. ABC folded, Meta folded. …  Good for Rupert Murdoch for standing firm.”

Trump is widely known for his litigious nature. It’s been estimated he has filed around 4,000 lawsuits throughout his lifetime, including suits against The Wall Street Journal, ABC News, CNN, The New York Times, Dow Jones and local newspapers such as The Des Moines Register. 

Though Trump sues the media often, he has yet to win in court. Most cases were dismissed or settled. Yet, even settling a case can have a chilling effect.

“One lesson Trump likely learned from his litigation experience is that lawsuits can be an effective form of leverage in business and other dealings,” wrote Professor Timothy Zick, author of “The First Amendment in The Trump Era.” “Indeed, even if a claim has no or little legal merit, it can be useful in terms of exhausting, intimidating, and silencing opponents.”

The July 2025 settlement between CBS owner Paramount and Trump, in which the studio agreed to pay Trump $16 million, came months after ABC News and anchor George Stephanopoulos settled for $15 million after falsely reporting that Trump was “found liable for rape.” Trump was found liable for sexual assault in a civil trial.

But a judge recently dismissed Trump’s $50 million suit against journalist Bob Woodward and his publisher, Simon & Schuster, for publishing audio from Woodward’s interviews conducted while writing a 2020 book on Trump’s first term as president.

“We cannot afford to have news organizations intimidated into silence, or citizens intimidated into silence, and still retain our democratic nature,” Robbins said. “But there is a serious risk that this may be revisited by the Supreme Court.”

Will Trump win?

Trump’s most recent defamation suit against The Wall Street Journal could serve as a bellwether for whether Sullivan could someday be overturned.

Trump has said Teddy Roosevelt is one of his favorite presidents. Perhaps there will be a future where Trump will, like Roosevelt, win a defamation case against the media. One thing is certain: the burden of proof still falls on Trump. At least, for now.