Assembling a group of House Republicans at the White House to talk trade last month, President Trump suddenly launched into a tirade about the congressman leading an extensive investigation into his presidency: his New York antagonist, Rep. Jerrold Nadler.
“I’ve been battling Nadler for years,” Trump told the GOP lawmakers, who were embarrassed by the outburst, according to several individuals in the room who spoke on the condition of anonymity to freely discuss the remarks.
Trump and Nadler are currently the main foes in a constitutional clash over executive power, as Nadler aggressively moves to investigate the president’s conduct and weighs whether to hold impeachment proceedings. But Trump’s jabs at Nadler were a fresh reminder that the animosity between the two native New Yorkers is personal as well as political — rooted in a decades-old fight over a tract of New York City real estate.
The feud between Trump, 72, and Nadler, 71, began in the 1980s when Nadler, a New York state assemblyman and later congressman, proved to be a major obstacle to a vast development project that Trump envisioned for Manhattan’s West Side, Nadler’s turf.
“Jerry was on him from Day One,” said Linda Rosenthal, a former Nadler aide who later won his state Assembly seat. “He keenly understood that this was a man who would try to get the government to pay for all his mostly bollixed attempts at development . . . His casinos failed. He lost money on deals. He left the banks on the hook for his bad financial plans. . . . He was just such a braggart and such an insincere person, but Jerry saw through that.”
Trump never forgave Nadler, and privately he has simmered about the chairman and his investigation, calling him an irritant who has long been out to get him and recounting their New York run-ins to aides. He was alarmed by the chairman’s early March demands to 81 of Trump’s close associates and business partners for a range of documents, including material on Russia’s election interference and the president’s finances.
Trump has told White House aides to block the requests as much as possible, according to a senior administration official who spoke on the condition of anonymity to discuss strategy.
The White House declined to comment. Nadler declined to be interviewed for this article.
The feud began in 1985, when Trump purchased a dilapidated former railroad yard in Nadler’s assembly district and proposed turning it into a mega-community: 7,600 apartments in six 75-story towers surrounded by television stations, a shopping mall, a massive 7,600-car parking garage and the world’s tallest building — a 150-story skyscraper.
Already considered a real estate go-getter in his late 30s, Trump wanted to call his development along the Hudson River between 59th and 72nd streets “Television City,” and he predicted that it would be “the greatest piece of land in urban America.”
But the proposal generated fierce community opposition from locals who feared that the area would become too commercialized and congested. Standing with them was Nadler, who wanted the city to buy the land and upgrade the rail system to preserve middle-class transportation jobs.
Opposition to the project helped Nadler burnish his liberal reputation as he fought the Queens-born real estate developer, whom many in Manhattan considered an interloper.
The two men came from widely different backgrounds. Trump was a developer, a son of wealth who reportedly flattered politicians to win tax breaks and financial assistance that could help his business.
Nadler was a son of a New Jersey chicken farmer who moved to New York when the farm went belly-up. Suspicious of big developers, he built his career siding with the working class and preferred scholarly justifications for his actions rather than impassioned rhetoric.
Trump was undeterred by the resistance. He invited Nadler to see models of his towers that would rise above the city. When Nadler inquired about the purpose of the soaring skyscraper, Trump said he wasn’t sure but knew he wanted to live in the penthouse, so high in the sky that he would have to call the concierge to find out what the weather was below.
Nadler told associates that he found the display “grotesque,” and it cemented in his mind an image of Trump as a greedy man trying to take advantage of the system. Nadler teamed with community groups to wage legal and procedural fights to scuttle the project.
“Trump only wanted to build what he wanted to build. . . . It was like a joke,” said Ruth Messinger, a Nadler ally who was on the New York City Council at the time and also strongly opposed Trump’s 150-story building. “Nadler was just representing his constituency, saying why they didn’t want it.”
As the project stalled, Trump offered a compromise, dropping his prized skyscraper, scaling back the heights of his proposed towers and agreeing to build a 22-acre park by the Hudson — the linchpin of the deal that included plans to tear down and relocate part of a highway obstructing waterfront views.
Nadler would have none of it. When he won the nomination to succeed the late U.S. representative Ted Weiss in a special election in the fall of 1992, Nadler talked openly about using his new power at the federal level to ensure that Trump didn’t receive a dime for his bid to move the highway.
Once in Washington, Nadler panned Trump’s plea for federal assistance as “Trump pork” and worked behind the scenes to write into law a prohibition on any money for relocating a stretch of the highway, a cost he put at $350 million.
“It is outrageous, at a time of deep budget cuts, that Mr. Trump would seek a down payment from working Americans for his luxury high-rise development in Manhattan,” Nadler said in July 1995. “Why should taxpayers be asked to chip in for this massive and wasteful boondoggle?”
Trump called Nadler’s estimates “garbage,” labeled the congressman “dumb” and accused him of playing “to his small group of constituents while ignoring the needs of the rest of the city.” He piled on the insults.
“If Nadler spent more time in a gymnasium losing weight, he would do the voters a bigger service,” Trump said. “He needs to lose about 200 pounds.”
Nadler, who had weight-loss surgery in 2002, has worked for decades to change his lifestyle and has reduced his size considerably.
After the congressman blocked the public funds, Trump tried to claim victory anyway, arguing that “Fat Jerry Nadler is doing me a favor” because he’d have to spend less money if the highway stayed put.
“He’s too stupid to realize it,” Trump said. “He’s making me a lot of money.”
Nadler’s office countered that the lawmaker “never went bankrupt and had to spend his father’s fortune to keep his family’s business afloat.”
When Trump pushed for a loan guarantee with the Federal Housing Administration, Nadler worked to deny Trump mortgage insurance, which would allow him to borrow money at a lower interest rate. He personally lobbied then-Housing and Urban Development Secretary Andrew M. Cuomo, pointing out that Trump’s apartments included only a small percentage of affordable housing units, so they did not qualify for assistance.
Trump later leaned on GOP allies to whom he had donated to secure an earmark for his project. It created an unusual dynamic, in which Trump-allied lawmakers lobbied for money that wouldn’t even go to their districts while Nadler worked to cut funds for development in his own neighborhood.
In the end, Trump never got the highway moved, but Nadler never got Trump to abandon the project entirely. Trump ensured the construction of 20 residential buildings, but in 2005, with parts of the 1.8 million-square-foot complex still under construction from years of delays and opposition, Trump sold the property for $1.8 billion.
After Trump’s election, residents of the apartment complex voted to have his name removed from the property, a repudiation of the man who fought for its very existence.
This year, with Democrats in the majority in the House, Nadler has built a massive legal team to scrutinize Trump’s moves, hiring high-profile lawyers who have criticized the president in the past.
Trump’s lawyer Rudolph W. Giuliani — who said he worked closely with and always got along with Nadler when he was New York mayor in the late 1990s — is encouraging Trump to resist the Judiciary Committee investigation because “they have already announced he’s guilty.”
Nadler, according to associates, is not intimidated by Trump. After Trump won the election, the congressman wrote about how the country could not normalize Trump’s conduct. The lawmaker’s allies have been surprised that Trump has not given him a public nickname, although Nadler often tells with pride the story of Trump calling him a political hack.
Rosenthal said that Nadler’s “tangles with Trump in the past make him perfectly suited” to investigate the president. “Trump knows what Jerry’s like. He knows how smart he is. He knows that he’s relentless. And Trump’s obviously upset that he can’t control him.”
Alice Crites contributed to this report.