Trump and/or his companies have been involved in 4,095 lawsuits over a span of 30 years according to a USA Today study. Several of those have involved media companies and journalists. Trump also regularly threatens lawsuits as a means of intimidating his critics.
|1984||Trump files his first lawsuit against an architect who criticized his plan to build "the world's tallest tower." chicagomag.com (See also Lawsuits)|
|1999||Trump withholds $1.5 million alimony payment from Marla Maples when she threatens to "tell the people what he is really like" if he runs for President. buzzfeed.com (See also Marla Maples, Women)|
|2005.10||A New York Times business reporter publishes a book about Trump, who later sues author for $5 billion for using low estimates for Trump's net worth. (Trump lost badly.) nationalreview.com|
|2007||Over the past ten years Trump as called Dallas Mavericks owner and reality TV competitor Mark Cuban a "loser," "Neanderthal," "dummy," and more. money.cnn.com|
|2013.02.06||Trump sues comedian Bill Maher for implying he's the son of an orangutan. forbes.com|
|2015.06.25||Univision cuts ties with Donald Trump's Miss USA pageant over racist remarks. latimes.com (See also 2016 Campaign, Mexican Americans, Mexico, Trump Business)|
|2015.06.26||Trump says Univision employees are now banned from his golf club. politico.com (See also 2016 Campaign, Trump Business)|
|2015.06.30||Donald Trump Sues Univision For $500 Million claiming they are, "suppressing his freedom of speech" by cutting ties with him after he made racist comments. npr.org (See also 2016 Campaign, Lawsuits, Trump Business)|
|2015.07.01||Macy's pulls Trump clothing line from stores. cnn.com (See also 2016 Campaign, Trump Business)|
|2015.07.01||Serta announces they will stop selling Trump brand mattresses due to Trump's racist comments. bloomberg.com (See also 2016 Campaign, Mexican Americans, Trump Business)|
|2015.07.07||PVH Corp. discontinues Trump menswear line in response to Trump making racist anti-Mexican comments. forbes.com (See also 2016 Campaign, Mexican Americans, Trump Business)|
|2015.07.14||Trump sends letter to LPGA head daring him to move the Women's British Open to another location besides Trump's golf course. businessinsider.com (See also 2016 Campaign)|
|2016||Trump threatens libel suits to intimidate (and always loses). medialaw.org|
|2016.02.11||Trump and Univision come to confidential settlement over Trump's $500 million lawsuit, which he filed after Univision canceled its plans to broadcast Trump's Miss USA pageant in retaliation for derogatory comments Trump made about Mexican immigrants. fortune.com (See also Mexican Americans, Immigrants)|
|2016.02.26||Trump: We're going to "open up" libel laws to make it easier to sue journalists. politico.com (See also Attempts to Discredit Media, Assaults on Civil Liberties)|
|2016.06.02||PGA announces they will move Tour from Trump golf course to Mexico. cnn.com (See also 2016 Campaign, Trump Business)|
|2017.01.11||Trump tweets, "Intelligence agencies should never have allowed this fake news to 'leak' into the public. One last shot at me. Are we living in Nazi Germany?" twitter.com (See also Attempts to Discredit Media)|
|2017.01.14||Trump starts MLK weekend by attacking civil rights activist John Lewis, who challenged the legitimacy of Trump's election win. theguardian.com (See also Unpresidential Behavior, Black Americans)|
|2017.01.21||Trump and his press secretary falsely accuse press of underestimating the size of inauguration crowds and inventing a rift between him and intelligence agencies over Russian election meddling. nytimes.com (See also False Statements, Russian Meddling in Election)|
|2017.01.21||Trump falsely accuses journalists of inventing a rift between him and spy agencies, and of deliberately understating the size of his inauguration crowd. nytimes.com (See also Attempts to Discredit Media, Assaults on Facts)|
Trump: "I have a running war with the media... They are among the most dishonest human beings on earth."
|2017.01.21||Trump says media are "among the most dishonest human beings on Earth" during speech at CIA headquarters. money.cnn.com (See also False Statements, Attempts to Discredit Media)|
|2017.01.21||Trump’s press secretary lashes out at press for accurately reporting inauguration attendance. washingtonpost.com (See also False Statements, Attempts to Discredit Media)|
|2017.02.09||Trump is added as a defendant in landmark 2015 lawsuit that claims U.S. government failed to protect citizens from dangers of global warming. scientificamerican.com (See also Climate Change, Environment)|
|2017.06.07||Fired FBI Director James B. Comey said Trump told him at the White House “I need loyalty, I expect loyalty” during their private dinner conversation in January, according to written remarks from Comey offering a vivid preview of his testimony Thursday before the Senate Intelligence Committee. washingtonpost.com (See also Corruption, Unpresidential Behavior, Legal Activity, Russian Meddling in Election, Michael Flynn)|
|2017.06.07||In his 9 one-on-one conversations with Trump, former FBI chief, James B. Comey said Trump pressured him for loyalty, sought forbearance for Michael Flynn and asked him to lift the “cloud” of a Russia investigation hanging over the administration. bloomberg.com (See also Legal Activity, Unpresidential Behavior, Michael Flynn, Russian Meddling in Election, Corruption)|
|2017.11.19||Donald Trump tweeted that he should have left three American citizens in jail after they were arrested for shoplifting in China. nytimes.com (See also Racism, China, Unpresidential Behavior)|
|2017.11.20||Randall Stephenson told antitrust enforcers that AT&T Inc. would see them in court after the Justice Department sued to block the company’s $85.4 billion bid to buy Time Warner Inc. saying, the lawsuit “stretches the very idea of antitrust law beyond the breaking point.” bloomberg.com (See also Censorship, Department of Justice)|
He reiterated that he wouldn't sell CNN to appease Washington.
|2017.11.21||Donald Trump took to Twitter to criticize Oakland Raiders running back Marshawn Lynch. cnn.com (See also Racism, Unpresidential Behavior)|
|Trump threatens to cut federal funds to UC Berkeley. sfchronicle.com (See also Unprecedented Actions, Assaults on Civil Liberties)|
Trump has a poor record when it comes to filing libel suits. Of the seven he has filed, four were dismissed, two were withdrawn, and one was won in arbitration.
The First Amendment makes it difficult for public figures to successfully sue for libel. A plaintiff who is a public official must prove the defendant acted with "actual malice." Truth is also almost always the ultimate defense and has been for even longer than the existence of the United States, when Andrew Hamilton successfully argued the point in a 1733 case called "Crown v. Zenger."
A USA Today analysis said of Trump's frequent lawsuit threats: "The threats can be effective. Even the possibility of a lawsuit by a rich, powerful opponent raises the specter of years of expensive and time-consuming litigation."