Donald Trump opposes the present strong freedom of the press in America by making it easier for the rich and powerful to sue reporters and news outlets for libel. Making
libel suits easy has been a traditional way to weaken freedom of the press in America. Many supporters of freedom of the press at the time of the First Amendment had in mind the case of
John Peter Zenger, a New York publisher jailed for "criminal libel," that is, for spreading the word that the acts of the government were bad. Zenger was acquitted. This case demonstrated the principle that truth is a defense to libel.
The other great attack on freedom of the press in America was settled by the Supreme Court of the United States in
New York Times v. Sullivan, 376 U.S. 254 (1964) Opponents of Jim Crow laws and practices ran an ad in the Times which had some errors in them.
E.g., Dr. Martin Luther King, Jr., had only been arrested four times in Montgomery protests instead of seven. Sullivan-- one of the three Montgomery Alabama city commissioners, the municipal elected officials-- Sullivan won a $500,000 judgment that was affirmed by the Alabama Supreme Court (
$3,827,265.37 in 2016 dollars). Had Sullivan won, it is likely that this defamation tactic would have broken King and the civil rights movement. The rule that
Sullivan established was that public figures could only win libel damages if they could prove that the defendants were wrong and had an intent to hurt them.