Judge Engoron’s $355 Million Penalty Makes One Thing Clear

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By the time New York Justice Arthur Engoron ordered Donald Trump on Friday to pay a staggering $355 million fine and barred him from conducting business in the state for three years, the former president’s imprint on the city that built him had already been vastly diminished. But the ruling, if upheld, may be the nail in the coffin.

The penalty levied against the Trump Organization—for overvaluing its assets in a scheme to enrich itself while defrauding banks—will require the former president to fork over a colossal amount, even for a self-proclaimed billionaire. Accounting for prejudgment interest charges, he will have to pay some $450 million in total, a sum that will likely require him to sell off assets. He might even have to offload his trademark property and longtime New York City residence, Trump Tower—if the state doesn’t seize it first. If that happens, the mythos of Trump, once synonymous with the gaudy glamour of New York City, will be all but erased from it, in an almost decadelong saga that now appears to be entering its final act.

Much of the rise and fall of Trump’s New York happened on the Upper West Side. In the 1980s, he laid out a grand vision to build “Trump City” along the Hudson River, on what he called “the greatest piece of land in urban America.” He promised to house up to 20,000 people and create a combined 5-million-plus square feet dedicated to retail space and entertainment studios. At the time, the New York Times editorial board wrote that it was clear Trump longed “to be a builder like the hero of Ayn Rand’s novel, so large that the skyline is his profile.” Trump City, the paper said, was Trump’s “bid for immortality.” The editorial also included the line “Time alone can distinguish between great dreams and vain illusions.”

Indeed, no such great dream came to pass. The project failed after a few decades of legal challenges and local opposition. (There have always been New Yorkers who have viewed Trump as the enemy.) So Trump settled for a smaller plan—six luxury buildings on Riverside Boulevard owned by others but branded as “Trump Place.”

Those buildings were emblazoned with Trump’s name from the 2000s until 2016. But that year, before he had even become president, the residents revolted. “For me, watching Trump talk about groping women and then seeing his name above my home was the breaking point,” a resident named Linda Gottlieb told the New York Times in 2016. “It was time to declare that we don’t want to live in a building bearing his name, or a country suffering his presidency.”

Gottlieb, who was paying almost $10,000 a month in rent at Trump Place, started a petition to ditch Trump’s name, an effort welcomed by the neighboring buildings. The Trump Organization unsuccessfully sued, and by 2019 the bold, gold letters spelling Trump were entirely scraped. The buildings became known solely by their street numbers.

Trump Place wasn’t the only outpost of the Trump brand to crumble. In December 2017, the Trump Soho, a hotel operated by the Trump Organization in downtown Manhattan, changed its name to the Dominick. While Trump’s D.C. hotel thrived during his presidency, visitors to New York in those years proved to be a different crowd. The hotel restaurant at the Trump Soho, Koi, was forced to close in 2017, citing declining business following the election. It became even clearer that the hotel’s association with Trump was cancerous when, in February 2019, the Dominick reported a significant spike in revenue and bookings after dropping the Trump name.

That fall, as Central Park’s Wollman skating rink was set to reopen for the winter, the Trump Organization quietly wiped the then president’s name from its branding—a major symbolic blow to Trump’s personal mythology about his success and a sign that even the Trump Organization knew that its branding was toxic in the city. On the campaign trail and in interviews before the 2016 election, Trump often cited the Wollman Rink as evidence of his qualifications to lead the country. He rescued the rink in the 1980s after the government couldn’t finish construction on it. As president, he promised, he would do the same for the entire country. “Wait’ll you see what I do,” he told supporters in Iowa ahead of the 2016 caucuses. “Remember the Wollman Rink in Central Park? You know, they couldn’t—years and years, they couldn’t do it. I knocked it up in four months.” The Central Park carousel, officially known as the Michael Friedsam Memorial Carousel, was also operated by the Trump Organization; the name “Trump Carousel” also disappeared from that attraction in 2019.

Scorned, Trump changed his official residence to Palm Beach, Florida. “I have been treated very badly by the political leaders of both the city and state,” he tweeted about New York in 2019. “Few have been treated worse.”

And then, after the Jan. 6 insurrection, the city escalated its fight. Then-Mayor Bill de Blasio announced he was canceling all city contracts with Trump, including Trump Links, the city-owned Bronx golf course, and the Wollman Rink. A judge declared the move illegal in 2022, but by then the skating rink had found a new operator, and the Trump Organization seemed to understand that it was unwanted. In 2023 it sold the rights to the golf course to Bally’s Corporation. On the final day of the civil fraud trial in January that ultimately took away Trump’s ability to do business in New York for the next three years, Mayor Eric Adams held a ribbon-cutting ceremony for the new “Bally Links.”

After Engoron’s ruling, it appears the Trump Organization is in an even more liminal state in New York. Though Trump and his children would surely love to move their business out of the state (perhaps to Palm Beach, as well), they are virtually prohibited from selling, transferring, or otherwise disposing of most “non-cash” assets without notifying the attorney general, court, or a court-appointed independent monitor. They also must give the monitor at least 30 days’ notice of “any planned or anticipated restructuring.”

It’s not totally over. Perhaps the Trump brand could bounce back after its time in purgatory. And Trump still has a few city landmarks emblazoned with his name: the Trump World Tower, the Trump International Hotel, Trump Parc, and Trump Palace—none of which he fully owns. Trump Tower remains the most recognizable, and perhaps his most cherished property. Being forced to relinquish it would be the ultimate defeat. The buyer, though, would likely be getting a good deal. In November, a three-bedroom property at Trump Tower sold for $6.125 million. Ten years earlier, when The Apprentice was still airing new episodes and you could ice-skate and golf at Trump-branded spots across the five boroughs, the same unit was purchased for $16.5 million.