The Trump Files: Witness Donald’s Epic Insult Fight With the Mayor of New York

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This post was originally published as part of “The Trump Files”—a collection of telling episodes, strange but true stories, and curious scenes from the life of our current president—on August 11, 2016.

Donald Trump is no stranger to high-profile feuds, but his long-running battle with New York City Mayor Ed Koch was epic even by Trumpian standards. Trump’s rise to fame and fortune overlapped almost perfectly with Koch’s three terms as mayor from 1978 to 1990, and Koch, who died in 2013, tangled with Trump over building plans, tax breaks, and even Trump’s demand for the city to evict street peddlers on Fifth Avenue near Trump Tower.

The feud reached its high (or low) point in 1987. Trump held the rights to a large chunk of land on the Upper West Side where he was hoping to build “Television City,” a huge development that included new studios for NBC and a 150-story skyscraper that would have been the tallest building in the world. But he also wanted tax breaks and zoning concessions from the city, and Koch wasn’t having any of it.

Koch rejected the tax break in May and then released a nasty series of letters the two men had sent each other about the decision. Koch said Trump’s project was too risky to justify giving away so much tax revenue, while Trump called Koch’s refusal “ludicrous and disgraceful.”

After the letters were released, Trump said the “moron” mayor should quit his job. “The city under Ed Koch is a disaster,” he told the New York Times. “If Donald Trump is squealing like a stuck pig, I must have done something right,” Koch fired back.

Days later, Trump was saying that Koch’s New York was “a cesspool of corruption and of incompetence,” while Koch was calling the developer “greedy, greedy, greedy” and “piggy, piggy, piggy“—before unironically declaring that he had “no intention of allowing this important matter to degenerate into a barnyard kind of contest.”

The fight then flared up again in August when Trump was interviewed for story by PBS’ MacNeil/Lehrer NewsHour. “Ed Koch could do everybody a huge favor if he got out of office and if they started all over again, because what Ed Koch has is nothing,” Trump said. “I would say he’s got no talent and only moderate intelligence,” he added later in the piece.

The insults even continued after Koch suffered a stroke (his doctors called it “trivial”) that same month. Koch called Trump a “flop” at a September press conference, and Trump responded by asking, “How can our idiot mayor go to Nicaragua when he can’t even run New York City properly?” after Koch announced he’d visit the Central American country as part of a peace delegation.

Eventually the name-calling died down, and the two men even shared a tense handshake in October 1987, but there was no love lost between them. In 1988, as Koch geared up to run for a fourth term, Trump threatened to dump $2 million into an anti-Koch ad blitz. That money never materialized, but, according to Newsday, Trump did donate a small amount to Koch’s primary opponent, David Dinkins—who defeated Koch and replaced him at City Hall.

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