Trump's legal team took issue with a book by Times journalists Susanne Craig and Russ Buettner titled Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success. They also said they were demanding damages over "false and defamatory statements" in the October 20 article "For Trump, a Lifetime of Scandals Heads Toward a Moment of Judgment" by Peter Baker and the October 22 piece "As Election Nears, Kelly Warns Trump Would Rule Like a Dictator" by Michael Schmidt.

The former article covered numerous wrongdoings by the president-elect and accusations against him, pointing out that he "is the only president in American history impeached twice for high crimes and misdemeanors, the only president ever indicted on criminal charges, and the only president to be convicted of a felony (34, in fact)," and that he has also boasted about sexually assaulting women and spearheaded numerous businesses that went bankrupt.

The latter article detailed comments by Trump's former chief of staff, John Kelly, who told the Times that the definition of fascism accurately describes Trump.

The president-elect himself said while campaigning that he planned to govern as a dictator only on "Day One" of his term in office.

"Governments and powerful figures threatening journalists and media outlets with costly legal battles and bankruptcy is a common tactic against press freedom in repressive countries."

Paltzik told the newspaper that the articles demonstrate the Times' "intention of defaming and disparaging the world-renowned Trump brand that consumers have long associated with excellence, luxury, and success in entertainment, hospitality, and real estate, among many other industries, as well as falsely and maliciously defaming and disparaging him as a candidate for the highest office in the United States."

The CJR reported that the Times responded to Paltzik's letter, telling him the newspaper stood by its reporting on Trump.

As Barry Malone, deputy editor-in-chief of the Thomson Reuters Foundation, said on social media on Friday, Trump's legal threats may be designed not to actually win billions of dollars in damages but "to tie the media up with time-consuming and often prohibitively expensive cases."

The Times and Penguin Random House threats were reported two weeks after Trump suedCBS News for another $10 billion, claiming an interview with Democratic Vice President Kamala Harris, who lost the November 5 election, was unfairly edited to present her in a positive light and qualified as "election interference."

CBS said it would "vigorously defend" its journalistic practices and called the lawsuit "completely without merit"—a similar response to the one by The Washington Post, which was accused by Trump on the same day of making an illegal in-kind donation to Harris.

Anne Champion, an attorney who has represented several journalists and CNN in legal cases initiated by Trump, told the CJR that the legal threats will likely have "a mental chilling effect" on reporters and news outlets in the United States as Trump prepares to take office.

"It is both conscious and unconscious," said Champion. "Journalists at smaller outlets know very well that the costs for their organization to defend themselves could mean bankruptcy. Even journalists at larger outlets don't want to burden themselves or their employees with lawsuits. It puts another layer of influence into the journalistic process."

Trump has a longstanding disdain for the media, saying numerous times during his first term that journalists were the "enemy of the people." During one campaign rally just before the election he said he wouldn't "mind" if reporters at the event were shot, and he called the media the "enemy camp" during his victory speech last week.

During his first term he also threatened to "take a strong look at our country's libel laws"—which are actually controlled by states, not the federal government—and ensure that "when somebody says something that is false and defamatory about someone, that person will have meaningful recourse in our courts."

The American Civil Liberties Union pointed out at the time that the First Amendment and the lack of federal libel laws would stand in Trump's way, but on Thursday Lachlan Cartwright wrote at CJR that "the drumbeat of legal threats signals a potentially ominous trend for journalists during Trump's second term in office."

As Washington Post columnist Karen Attiah noted on the social media platform Bluesky, "governments and powerful figures threatening journalists and media outlets with costly legal battles and bankruptcy is a common tactic against press freedom in repressive countries."