Former President Donald Trump sued CNN for defamation on Monday, seeking $475 million in punitive damages, escalating his feud with US news organizations that have criticized his career.

The 29-page lawsuit, filed in the United States District Court for the Southern District of Florida, claims CNN participated in a “campaign of dissuasion in the form of libel and slander” that “escalated in recent months” because the network feared Trump would run for president again. CNN’s use of the words “racist” and “insurrectionist,” as well as associations made between the former president and Adolf Hitler, were challenged in the lawsuit.

Trump has a history of being highly litigious against media critics, though these legal challenges have largely failed. In 2020, his campaign sued The Washington Post and The New York Times separately for libel over opinion pieces linking the campaign to Russian election meddling. (The lawsuit against the Times was dismissed, but the lawsuit against The Post is still pending.) Trump’s campaign also sued CNN in 2020 for libel over an op-ed, which was later dismissed.

Jessica Levinson, a Loyola Marymount University law professor who reviewed the latest suit, believes Trump has “no legal path forward.”

“I see no false statements of fact that were made with actual malice,” she said, adding that an “enormous amount” of the CNN comments described as defamatory in the lawsuit appeared to be opinions.

Trump’s lawyers cite numerous CNN clips and articles in the lawsuit, including a 2019 interview with singer Linda Ronstadt, who compared aspects of Trump’s presidency to Nazi rule in Germany. According to the attorneys, Ronstadt “is a singer, not a historian,” and the interview was a “pretext to repeat CNN’s message under the guise of real ‘reporting.'”

Trump, as a public figure, must meet a higher standard to demonstrate that CNN defamed him. His lawyers must demonstrate that CNN made false statements about Trump that were presented as fact, and that the network had knowledge of the false statements or a reckless disregard for the truth, a standard that has historically been difficult to meet, according to Levinson.

CNN labeled Trump in ways that were “neither hyperbolic nor opinion,” according to Trump’s lawyers, and the channel acted with “real animosity” to cause him “true harm.”

Attorneys for the former president did not immediately respond to requests for comment Monday evening. CNN’s representative declined to comment on the suit.

According to Levinson, the most likely outcome of Trump’s legal challenge is that it will be dismissed once CNN files a motion to dismiss the suit. If the case goes to trial, both sides will be able to request evidence from each other in order to debate the veracity of CNN’s statements. That could be detrimental to Trump in the long run, she said, especially if the statements are found to be true.

“I think it’s really about trying to chill speech against the former president,” she said. “It’s a warning shot to media outlets that he intends to make good on threats of suing for defamation. And for some outlets, that could ultimately put them out of business.”