Trump’s latest move against Harvard comes as the president continues to lean on lawsuits and threats as tools in disputes with critics and institutions, an approach that dates back decades, according to an Associated Press review of cases and statements.
In the new matter, the U.S. Department of Justice is suing Harvard University, shortly after Trump took issue with a New York Times story about his fight with the school. Trump also recently threatened comedian Trevor Noah on Truth Social after Noah connected Trump to Jeffrey Epstein during the Grammy Awards show. “Get ready Noah, I’m going to have some fun with you!” Trump said in the post.
Middlebrooks, the Florida-based judge who handled Trump’s earlier case against Hillary Clinton, criticized Trump’s use of litigation in an order related to that dispute. Middlebrooks described Trump as “the mastermind of strategic abuse of the judicial process,” and wrote that Trump was a “sophisticated litigant … repeatedly using the courts to seek revenge,” according to the AP account of the judge’s language.
The pattern the review outlines includes disputes over discrimination allegations in Trump’s real estate business and conflicts that reached court even as Trump attempted to preserve public support. In the early 1970s, the Trump organization came under attention from state and federal authorities after prospective Black tenants complained of being denied apartments. The U.S. Department of Housing and Urban Development accused the Trumps of violating the 1968 Fair Housing Act, and AP said investigators at one point counted seven Black families across 3,700 apartments in Trump Village, citing Trump biographer Maggie Haberman, and that a Trump employee later testified that documents had a special code to flag Black applicants.
Trump responded by countersuing the federal government for $100 million in 1973, AP said, describing that effort as aided by Trump’s lawyer and mentor Roy Cohn. The two sides ultimately settled, but AP said the settlement took until 1975 after about 18 months of headline-generating coverage in New York media. The AP review said the consent decree included no admission by Trump that he had broken the law.
AP also said Trump later framed his approach to disputes in his own words in the 1987 book “Art of the Deal,” writing: “I’d rather fight than fold, because as soon as you fold once, you get the reputation of being a folder.” The review describes that line as reflecting a recurring stance toward legal conflict and public messaging.
Another example in the AP review traces back to Trump’s attempt in the early 1980s to redevelop 100 Central Park South by seeking to evict rent-controlled tenants. Tenants fought the effort, and Trump sued tenants’ lawyers in 1985 for $105 million, AP said. The suit was thrown out, and AP reported that Trump paid the defendants’ legal fees.
The AP review also described historical conflicts around claims about development plans and business worth, including a dispute over a proposed 150-story development off the tip of Manhattan. During that period, Trump sued Pulitzer Prize-winning critic Paul Gapp and the Tribune Co. for $500 million after Gapp mocked the proposal, AP said. A federal court dismissed Trump’s suit, according to the review.
Looking forward from Trump’s earlier business era, AP said Trump’s litigation strategy has followed him into politics, including using lawsuits in response to political investigations and media coverage. The AP review said his 2022 lawsuit tied to a probe into Russia’s role in the 2016 campaign was dismissed by Middlebrooks, who wrote that the case should “never have been brought” and identified it as part of “a continuing pattern of misuse of the courts by Mr. Trump and his lawyers.” AP said the judge’s order required Trump to pay defendants’ legal fees.
The AP review further said Trump has pursued settlements against major television news networks related to statements about him. In 2024, ABC News agreed to pay $15 million for Trump’s future presidential library and $1 million in legal fees tied to anchor George Stephanopoulos’ on-air legally inaccurate assertion about Trump being civilly liable for raping E. Jean Carroll. In 2025, AP said Paramount, which owns CBS, settled with Trump after he sued over how “60 Minutes” edited a Kamala Harris interview during the 2024 campaign, with Paramount agreeing to pay $16 million toward Trump’s future presidential library.
AP said Trump cited those cases in support of his threat to sue Noah, then followed with the threat to demand $1 billion from Harvard. The review also says Trump previously pressed for $500 million from the school for other educational programs.
The AP review added that Trump’s most consequential litigation demand framed by the president’s opponents concerns taxes. It said Trump has not released his tax returns, that The New York Times and ProPublica published stories detailing how Trump paid little or no federal income taxes in years after claiming substantial losses, and that an IRS contractor Charles Edward Littlejohn in 2024 was sentenced to five years in prison after pleading guilty to leaking Trump’s tax information to news outlets between 2018 and 2020. AP said Trump has not sued the media outlets in response, but is suing the IRS for $10 billion, which AP characterized as the largest demand by Trump as a plaintiff.