Trump’s Harvard move reflects one of his go-to tactics: Lawsuits

Donald Trump’s decades-long legal offensive has been a defining characteristic of his career as he frequently turns to the courts to settle scores and fight opponents, a strategy that continues through his presidency.

From his earliest days in his father’s real estate business to his time in the White House, Trump has demonstrated a consistent willingness to threaten lawsuits and initiate legal action against individuals, organizations, and even government entities.

U.S. District Judge Donald Middlebrooks once characterized Trump as “the mastermind of strategic abuse of the judicial process” and “a sophisticated litigant repeatedly using the courts to seek revenge,” highlighting a pattern that spans Trump’s public life.

Recently, Trump has set his sights on new targets. His Justice Department is pursuing legal action against Harvard University, shortly after Trump expressed displeasure with a New York Times article about his conflicts with the institution. He has also threatened comedian Trevor Noah following comments Noah made during the Grammy Awards connecting Trump to Jeffrey Epstein.

“Get ready Noah, I’m going to have some fun with you!” Trump warned on his Truth Social platform, signaling another potential lawsuit.

Trump’s litigious history began in earnest in 1973 when the federal government accused the Trump family real estate business of violating the Fair Housing Act by discriminating against Black applicants. Investigators reportedly found just seven Black families across 3,700 Trump apartments, and a Trump employee later testified that the company used special coding to flag Black applicants.

Rather than address these allegations, Trump, guided by his mentor and attorney Roy Cohn, countersued the federal government for $100 million (approximately $700 million in today’s dollars). After generating headlines for 18 months, Trump eventually settled in 1975, agreeing not to discriminate while avoiding any admission of wrongdoing.

Trump explained his philosophy in his 1987 book “The Art of the Deal”: “I’d rather fight than fold, because as soon as you fold once, you get the reputation of being a folder.”

This approach continued in the 1980s when Trump attempted to evict rent-controlled tenants from 100 Central Park South to demolish the building. When tenants fought back, Trump sued their attorneys for $105 million. The court not only dismissed the suit but ordered Trump to pay the defendants’ legal fees. Attorney Martin London later wrote that one of those attorneys, Rick Fischbein, framed Trump’s check after depositing it – and ironically, Fischbein later became one of Trump’s own lawyers.

During the same period, Trump proposed a 150-story development near Manhattan. When Chicago Tribune architecture critic Paul Gapp criticized the project as “one of the silliest things anyone could inflict on New York,” Trump sued the Pulitzer Prize winner and the Tribune Company for $500 million, claiming the criticism had killed the project. A federal court dismissed the case.

Trump’s sensitivity about his finances became apparent in 2005 when he sued author Timothy O’Brien for $5 billion after O’Brien’s book “TrumpNation” suggested Trump’s net worth was between $150-250 million rather than the billions he claimed. Courts in New Jersey rejected Trump’s lawsuit.

After becoming president, Trump continued this pattern. In 2022, he filed a lawsuit against Hillary Clinton and others, alleging a conspiracy to cost him the 2016 election, despite having won. Judge Middlebrooks dismissed the case, ordering Trump to pay defendants’ legal fees and writing, “This case should never have been brought. A continuing pattern of misuse of the courts by Mr. Trump and his lawyers undermines the rule of law.”

Trump has recently scored two substantial settlements from media organizations. ABC News agreed to pay $15 million toward Trump’s future presidential library after anchor George Stephanopoulos incorrectly stated on air that Trump had been found civilly liable for raping E. Jean Carroll. Similarly, Paramount settled with Trump for $16 million after he sued over CBS’s editing of a Kamala Harris interview during the 2024 campaign.

Trump’s most ambitious lawsuit targets the U.S. government itself. After the New York Times and ProPublica published stories based on leaked tax returns showing he paid little or no federal income tax for years, Trump sued the IRS for $10 billion – his largest demand ever. If successful, this unprecedented claim would effectively have American taxpayers funding his windfall.

This decades-long pattern of litigation reveals how central lawsuits have been to Trump’s business and political strategy – using the courts not just as a venue for legitimate grievances but as a tool for intimidation, publicity, and settling personal scores.