Politics

A 37-Year-Old Feud Might Explain Donald Trump’s Bizarre NYC Democratic Endorsements

Nadler speaks into a bullhorn being held by someone else, who is wearing a mask.
House Judiciary Committee Chairman Jerry Nadler speaks at a vigil to commemorate the first anniversary of the attack on the U.S. capitol by supporters of former president Donald Trump on January 06, 2022 in New York City. Spencer Platt/Getty Images

Donald Trump is taking the piss out of New York City politicians, as the British might put it, pretending to endorse two Democratic candidates in next week’s congressional primary, knowing that—in their overwhelmingly liberal districts—he can only hurt them by association.

On his social-media platform Wednesday, the former president—who is deeply unpopular in his former hometown—endorsed Daniel Goldman, one of several contenders in a newly created district that includes Lower Manhattan and the more fashionable parts of Brooklyn, and Rep. Carolyn Maloney, an incumbent who’s in a tight race against another incumbent in a court-ordered fusion of districts, one on the Upper East Side, the other on the Upper West.

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Trump clearly despises and possibly fears Goldman, who was the Democrats’ chief counsel—and lead interrogator—in the House impeachment hearings of 2019. So, in a low-brow retread of Mark Antony’s funeral oration, he comes to praise Goldman, not to bury him. “It is my great honor to Strongly Endorse him,” Trump posted, “I do this not because of the fact that he headed up the Impeachment Committee and lost, but because he was honorable, fair, and highly intelligent.” With a backhanded insult and “apparent sarcasm,” as the New York Post noted for those who didn’t read closely, Trump added, “While it was my honor to beat him, and beat him badly, Dan Goldman has a wonderful future ahead.”

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Some of Goldman’s primary foes leapt on Trump’s statement. New York State Assemblywoman Yuh-Line Niou said, “Donald Trump just endorsed my multi-millionaire opponent, in case you needed a reminder of what the stakes are… choose your fighter.”

Rep. Mondaire Jones, a congressman whose incumbent seat was eliminated in a redistricting and is now forced to run against Goldman, tweeted, “Trump says he’s backing Goldman because he wants progressives to lose and because Goldman failed to hold him accountable the first time. New York should not send this man to Congress.”

Goldman, an heir to the Levi Strauss & Co. fortune but also a former federal prosecutor with strong liberal bona fides, dismissed the endorsement and his opponents’ efforts to exploit it. “This is a pathetic attempt at fooling Democrats who are far smarter than Trump is,” he tweeted. “Buckle up Donald. Dan’s coming for you.”

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Few New York Democrats are likely to believe that Goldman and Trump are joined in any way, especially if they read the full text of Trump’s tweet. After saying he endorsed Goldman, Trump couldn’t resist a spree of pure self-indulgence: “He was not easy to beat,” Trump wrote, referring to the Senate’s subsequent vote to acquit him of the House impeachment, “but winning against him made me realize just how very talented I am!”

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Trump’s mock-support of Maloney is a bit more puzzling. He hates her opponent, Rep. Jerry Nadler, dating back to a bitter feud nearly four decades ago. So, by the logic that led him to wrap his toxic arm around Goldman, he should have endorsed Nadler. Is he indulging in reverse-reverse psychology?

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It’s worth reviewing the facts of  the Trump-Nadler feud to decipher what’s going on. It began in 1985, when Trump, then an up-and-coming real estate mogul, paid $115 million for an abandoned rail yard on Manhattan’s West Side and unveiled plans to turn it into the city’s largest development—six 75-story skyscrapers holding 8,000 apartments, 10,000 parking spaces, a massive shopping mall, TV studios, and, at the center of the complex, a 150-story tower, where he would live on the top floor, literally above the clouds.

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Opposing his plans was a group of neighborhood activists, led by Nadler, then a state assemblyman, who continued the role opposing the plans after he was elected to Congress in 1992. A crucial part of Trump’s plan—relocating a stretch of the West Side Highway—involved federal subsidies worth $300 million. Nadler blocked the funding. He also lobbied then-President Bill Clinton’s Secretary of Housing and Urban Development, a young Andrew Cuomo, to reject Trump’s request for federal mortgage insurance on the grounds that the project contained no low-income units.

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Trump fought back, railing at Nadler in the local tabloids, calling him “stupid,” “dumb,” and “Fat Jerry.” (Nadler weighed more than 300 pounds at the time; he later lost weight through gastric surgery.)

He negotiated with the City Council, and even with Nadler, to scale down the project—but not enough to secure a deal. Hemorrhaging money from other projects, he sold the rail yard, on which he’d started to construct 20 buildings (known as Trump Place), to a group of Hong Kong businessmen. It was quite a deal. The Hong Kong businessmen paid Trump $90 million, assumed his debts ($250 million) and back taxes ($6 million), and let him retain 30 percent ownership of the complex.

Ironically, Nadler saved Trump. The project was ill-fated from the get-go; had he gone through with it, he would have lost hundreds of millions of dollars more. The Hong Kong deal saved him from personal bankruptcy, gave him money to start new projects, and sealed his reputation as a great deal-maker, which led to The Apprentice and the myth that founded his campaign for the presidency.

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This whole story vanished into the esoteric annals of Manhattan real-estate lore, until 2019, when Nadler, as chairman of the House Judiciary Committee, opened hearings into Trump’s potentially impeachable wrongdoings. Eventually, the probe was passed to Rep. Adam Schiff and the House Intelligence Committee, but for a moment, the feud reignited. “Nadler has been fighting me for years and years in Manhattan—not successfully,” Trump complained.

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And now Trump is putting down Nadler again. But why didn’t he put him down harder by endorsing him? My guess is that he hates Nadler so much, he couldn’t bring himself to go quite that far, even in jest.

After endorsing Maloney, he did have some faux-nice words for his longtime nemesis:

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On the other hand, Jerry Nadler is likewise a hard-driving man of the people, whose energy and attention to detail is unlike anyone else in Congress. He is high energy, sharp, quick-witted, and bright. You can’t go wrong with either, but Carolyn Maloney is the better man… [S]he will never let our Conservative Movement down!

This is also bizarre, as Maloney is hardly a conservative. Then again Trump is nothing if not a bizarre presence on the political landscape, a scarred figure whose mission in life is to spread malice, menace, and mayhem, all in service of massaging his own ego and jockeying for power.

In these two New York Democratic congressional races, he may think he’s being clever—but his strategems won’t amount to squat.

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