The Trump Files: The Time Donald Sued Someone Who Made Fun of Him for $500 Million

He wanted to build the world’s tallest building. He didn’t like the way people responded.

Ivylise Simones


Until the election, we’re bringing you “The Trump Files,” a daily dose of telling episodes, strange but true stories, or curious scenes from the life of presumptive GOP nominee Donald Trump.

Donald Trump being Donald Trump, he more than once aspired to build the world’s tallest skyscraper. In 1984, it looked like he might get his chance.

That July, Trump told the media he was eyeing a soon-to-be-constructed section of landfill on the East River in Lower Manhattan as the site for a 150-story tower. “New York City deserves to have the tallest and greatest building in the world, and I would be very interested in doing it,” he told the New York Times. Trump’s proposed 1,940-foot combination office, apartment, and hotel building would smash the height record then held by the Sears Tower in Chicago by nearly 500 feet.

Reactions were skeptical. The Associated Press reported that Paul Goldstein, the manager of the community board for the area where the tower would stand, literally giggled as he considered the idea. “We’ve had some bizarre development proposals down here, but this takes the cake,” he said. In Chicago, architecture critic Paul Gapp ridiculed Trump’s plan in an article for the Chicago Tribune. “The world’s tallest tower would be one of the silliest things anyone could inflict on New York or any other city,” he said. Trump hadn’t produced any drawings of the tower, so the story was accompanied by a conceptual sketch of the building as dreamed up by the Tribune, with Gapp explaining why the likely end product would be pointless and inefficient.

Trump decided the best course of action was to sue Gapp and the Tribune for libel—and $500 million in damages. He claimed Gapp’s review had “virtually torpedoed” the project and subjected him “to public ridicule and contempt, all of which have caused him to suffer embarrassment and financial harm.” The Tribune’s drawing was deemed “an atrocious, ugly monstrosity” by Trump’s lawyers.

The case was dismissed about a year later, but it cost the Tribune $60,000 in legal fees to get the angry billionaire off its back, according to the Washington Post.

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