Asking for $475 million in punitive damages, Donald Trump has sued the Cable News Network (CNN) for allegedly defaming him with slanderous and libelous content during their coverage of his political career.

Filed in the District Court of Southern Florida, the complaint alleged that “CNN has sought to use its massive influence — purportedly as a ‘trusted’ news source — to defame the Plaintiff in the minds of its viewers and readers for the purpose of defeating him politically.”

Trump further suggested that the media organization intentionally waged a “campaign of dissuasion in the form of libel and slander,” which “has only escalated in recent months as CNN fears the Plaintiff will run for president in 2024.”

Specifically, the complaint pointed to the defamatory labels of “racist,” “Russian lackey,” “insurrectionist,” and “Hitler.” Going further, Trump’s legal team offered that CNN met the legal definition for defamation due to the organization “acting with real animosity for the Plaintiff and seeking to cause him true harm.”

“It is the stuff of tabloids cloaked as ‘honored’ news,” the complaint alleged.

A significant portion of the filing focused on CNN’s that Trump is akin to Nazi leader Adolf Hitler, “CNN published these defamatory statements with actual malice” and “published the statements with reckless disregard for their truth or falsity.”

Summons were sent to CNN on October 3, giving them 21 days to respond to the complaint. If the organization fails to respond within that time frame, “judgment by default will be entered against you for the relief demanded.”

CNN has thus far declined to comment and has not yet filed an answer.

American judicial precedent established in cases like New York Times v. Sullivan (U.S. Supreme Court, 1964) has made it increasingly difficult for a famous person or someone in a position of power to win a defamation lawsuit.

In that case, Justice William Brennan wrote the unanimous opinion, explaining that “erroneous statement is inevitable in free debate, and that it must be protected if the freedoms of expression are to have the ‘breathing space’ that they ‘need … to survive.’”

To that end, public officials must present evidence “to show actual malice” with “the convincing clarity which the constitutional standard demands.”

This is a high bar, however, and in a concurring opinion, Justice Hugo Black noted that actual malice “is an elusive, abstract concept, hard to prove and hard to disprove.”

Trump has previously sued other media organizations for alleged defamation in the past. Many of those lawsuits were dismissed by the courts.

When the former president himself has been sued for defamation, he has succeeded in winning some noteworthy suits. A recent one was brought by Summer Zervos, a former reality television show contestant who accused “The Apprentice” star of sexual assault.