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Trump's shambolic empire faces long odds for one more comeback

Caleb Melby, Tom Maloney and Max Abelson, Bloomberg News on

Published in News & Features

On the day Donald Trump was getting impeached in Washington, the lobby of his New York tower at 40 Wall St. was almost silent. Few footsteps smudged the shiny marble.

But up the dark and golden elevators, trouble was stirring in one of the billionaire’s most valuable properties. Inside one law office, two partners had clashed over whether to keep paying rent to a landlord who encouraged the Capitol’s deadly riot. On the 24th floor, a nonprofit that fights tuberculosis was exploring options for leaving. On the seventh, the Girl Scouts were figuring out how to break their lease.

And in the basement, vintage bank-vault doors that weigh more than 10 tons stood wide open. There, in a club room that Trump renovated, the news was playing on a jumbo television to an audience of empty armchairs just as Congress voted against him.

So it goes in Trump’s empire as his presidency slouches toward the end.

The Trump Organization, run by sons Eric and Don Jr., was struggling with the devastating consequences of the COVID-19 pandemic even before their father incited a raid on Congress. Efforts to sell his Washington hotel were shelved, his office buildings were losing value amid a glut of space in Manhattan, and his golf courses were facing the reality that younger generations aren’t so interested.

Trump entered office worth $3 billion. Despite soaring stock prices and his own tax cuts, he will leave about $500 million poorer, according to the Bloomberg Billionaires Index.


His buildings are saddled with more than $1 billion in debt, most of it coming due in the next three years and more than a third of it personally guaranteed. Refinancing would mean finding lenders and corporations willing to work with history’s only twice-impeached ex-president.

“Nothing like this has ever happened to him,” said Barbara Res, who was an executive in Trump’s company for years. “Will he come back? My gut tells me yes, because he always comes back. But he won’t come back the same.”

Trump already has survived corporate bankruptcies, rough times in Atlantic City, a school that ended with probes and dead-end brand journeys for Trump Steaks, Trump Vodka and even an airline. The man who made “America First” his catchphrase could now hunt overseas for partnerships and licensing deals.

Even so, Deutsche Bank AG, his longtime financier, won’t touch him anymore. Signature Bank, where his daughter Ivanka once served on the board, is closing his accounts. Cushman & Wakefield Plc, a broker for 40 Wall St., is cutting ties, and PGA of America is steering clear.


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