SWFL.io - Local NewsATLANTA (AP) — Donald Trump has played many roles. Real estate developer. Marketing extraordinaire. Reality TV host. Candidate. President — twice.
Another part has been constant through all of them: plaintiff.
Trump both threatens lawsuits and files them with aplomb — against individuals, institutions, even the people who elected him. Sometimes the threats are just that, and no lawsuit materializes. And, certainly, Trump has found himself on the receiving end of many lawsuits and legal challenges. But his own litigious bent goes back decades, and it has continued during his time in the White House.
U.S. District Judge Donald Middlebrooks once described Trump as “the mastermind of strategic abuse of the judicial process.” Trump, Middlebrooks declared in a short-lived 2022-23 Trump case against Hillary Clinton, is a “sophisticated litigant … repeatedly using the courts to seek revenge.”
The president named his latest potential targets this week: Harvard University, after he didn’t like a New York Times story about his fight with the school, and comedian Trevor Noah, who connected Trump to Jeffrey Epstein during the Grammy Awards show.
“Get ready Noah, I’m going to have some fun with you!” Trump blasted on Truth Social.
Here are some highlights of Trump's torts and threats.
Trump started in his father's Queens-based real estate business. They attracted attention from state and federal government authorities in the early 1970s after prospective Black tenants complained of being denied apartments.
Eventually, the U.S. Department of Housing and Urban Development accused the Trumps of violating the 1968 Fair Housing Act. At one point, investigators counted seven Black families across 3,700 apartments in Trump Village, according to Trump biographer Maggie Haberman, and a Trump employee later testified that documents had a special code to flag Black applicants.
Trump dug in. Aided by his lawyer and mentor Roy Cohn, he countersued the federal government for $100 million in 1973 — equivalent to about $700 million today.
They ultimately settled the dispute, but not until 1975, after spending 18 months generating headlines in New York media to counter the government's case. Trump promised not to discriminate against prospective renters in the future, but the consent decree he signed included no admission that he'd broken the law in the first place.
Trump recounted in “Art of the Deal,” his 1987 ghost-written book: “I’d rather fight than fold, because as soon as you fold once, you get the reputation of being a folder.”
Trump wanted to evict rent-controlled tenants from 100 Central Park South so he could raze the building in the early 1980s. They fought him and in 1985 he sued the tenants’ lawyers for $105 million ($300 million-plus today). The suit got thrown out and Trump paid defendants’ legal fees.
Attorney Martin London represented one of the defendant lawyers, Rick Fischbein, and wrote in his memoir that Fischbein framed his check from Trump after it was deposited. Fischbein later became one of Trump’s attorneys.
Trump eventually dropped his eviction suit, redeveloped the building and allowed tenants to remain there under rent-control agreements.
During the same period, Trump proposed a 150-story development off the tip of Manhattan. A Chicago Tribune critic, Paul Gapp, mocked it as “Guinness Book of World Record architecture” and “one of the silliest things anyone could inflict on New York or any other city.”
Trump sued the Pulitzer Prize winner and the Tribune Co. for $500 million (about $1.5 billion today), saying Gapp's assessment killed the project.
A federal court dismissed the suit.
In 2005, a decade before Trump launched his presidential bid and as his TV career blossomed with NBC'S “The Apprentice,” author Timothy O'Brien wrote “TrumpNation: The Art of Being the Donald.”
The book alleged that Trump was not a billionaire at all and worth between $150 million and $250 million. Trump sued and asked for $5 billion (now $8 billion-plus), saying O'Brien harmed his ability to make business deals. A New Jersey court threw out the lawsuit, and an appeals court agreed.
Trump defeated Hillary Clinton for president in 2016. That did not stop him from making her the lead client, along with a litany of others, in a 2022 lawsuit that alleged a vast conspiracy to cost him the election.
It was part of Trump's push back against a Justice Department investigation of Russia's role in the campaign. The inquiry concluded that Russia interfered in U.S. political discourse in “sweeping and systematic fashion” to help Trump and harm Clinton. But the Justice Department stopped short of saying whether Trump was involved. Trump was explicitly not exonerated in the final report, but he still used it to assert that “the Russia hoax” was a deliberate plot against him.
Middlebrooks, the Florida-based judge who got the Trump v. Clinton case, disagreed, tossed Trump's lawsuit and made Trump pay defendants' legal fees — which combined with his reached into the millions.
“This case should never have been brought,” Middlebrooks wrote in a scathing January 2023 order. “A continuing pattern of misuse of the courts by Mr. Trump and his lawyers undermines the rule of law.”
Since becoming president, Trump has scored two settlements for his presidential library after suing major television news networks.
ABC News agreed in 2024 to pay $15 million to Trump's future library and $1 million in legal fees after anchor George Stephanopoulos’ legally inaccurate assertion on air that Trump had been found civilly liable for raping writer E. Jean Carroll. In fact, a New York jury found Trump had sexually assaulted Carroll in the mid-1990s but concluded she did not prove Trump raped her “within the narrow, technical meaning of a particular section of the New York Penal Law.”
Paramount, which owns CBS, settled with Trump in 2025 after he sued over the way “60 Minutes” edited a Kamala Harris interview during the 2024 campaign. Paramount agree to pay $16 million toward Trump's future presidential library.
Trump cited those cases in his threat to sue Noah. He followed that a day later with his threat to command $1 billion from Harvard. He's pushed previously to get $500 million from the school for other educational programs.
Trump has bucked presidential tradition by never releasing his tax returns. But after he became president, The New York Times and ProPublica published stories detailing how Trump went years paying no or little in federal income taxes after claiming substantial losses.
In 2024, former Internal Revenue Service contractor Charles Edward Littlejohn, of Washington, D.C. — who worked for Booz Allen Hamilton, a defense and national security tech firm — was sentenced to five years in prison after pleading guilty to leaking Trump's tax information to news outlets between 2018 and 2020.
Trump has not sued the media outlets in response. Instead, he is suing the IRS for $10 billion.
It's the largest demand ever made by plaintiff Trump, and if he were successful, it would be U.S. taxpayers paying the damages.