The Trump Files: Donald Wanted to Build an Insane Castle on Madison Avenue

It was supposed to have a moat.

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.

If Donald Trump had gotten his way in 1984, a New Yorker wouldn’t have had to travel to Atlantic City to visit the Trump Castle. The real estate mogul wanted to build a castle-like skyscraper right in Manhattan—complete with a moat and drawbridge.

The New York Times described the planned luxury condo building as “a 60-story castle, Trump Castle, six cylinders of varying heights with gold-leafed, coned and crenelated tops to be built at 60th Street and Madison Avenue.” A Miami Herald story from 1986 even claimed that the bridge was to be guarded, like an urban Riverrun. Architect Philip Johnson, who proposed the building’s moat and drawbridge, told the Times that the medieval defenses were “very Trumpish.” He added, “Trump is mad and wonderful.”

Sadly, the fortress on the Upper East Side was abandoned when Prudential, which owned the site, decided not to proceed with the project. “We didn’t want to do a deal that depended on selling apartments for $1.5 million each to break even,” a Prudential executive told the Los Angeles Times. And when the Trump’s Castle casino opened in Atlantic City in 1985, it was a boring old rectangle with not even a single coned top.

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