Three decades before he was first elected president, Donald Trump had big plans for a 26-acre building site near the South Street Seaport in Manhattan. "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 on July 30, 1984. He imagined a 150-story structure, including offices, apartments, and a hotel, that would be 1,940 feet high, surpassing Chicago's Sears Tower, then the world's tallest building, by nearly 500 feet.
Paul Gapp, the Chicago Tribune's architecture critic, did not think much of that plan. "The only remotely appealing aspect of Donald Trump's proposed 150-story Manhattan skyscraper, announced several days ago, is that it would not be done in the Fence Post Style of the 1970s," Gapp wrote. "The world's tallest tower would be one of the silliest things anyone could inflict on New York or any other city." Trump was indulging in "Guinness Book of World Records architecture," Gapp said.