The Bankruptcy of Donald Trump

The so-called billionaire's inability to pay his tax fraud fines exposes his career of bombast and lies

A financially troubled man in his Florida club. (Photo by Alon Skuy via Getty Images)

He’s a very, very successful businessman, a multi-billionaire, an incredible winner, he told America, with a net worth of “well over $10 billion.” He’d been touting his winning ways for decades, well before publishing The Art of the Deal in 1987, not just when he pretended to be that capable guy on The Apprentice with the editorial trickery of TV producer Mark Burnett.

In a news interview in 2011, when he was ostensibly mulling a run for president, Donald Trump said that “part of the beauty of me is that I'm very rich. So if I need $600 million, I can put $600 million myself. That's a huge advantage. I must tell you, that's a huge advantage over the other candidates."

Four years later, on June 16, 2015, when he descended a golden escalator and declared himself a candidate for president, he is best remembered for telling America that Mexico was sending rapists and criminals, that they were using our country as “a dumping ground.”

But he also took plenty of time in his announcement to emphasize how rich and successful he was (even while relying on other peoples’ money). He told the story of a big bank that came to him and said, “Donald, you don't have enough borrowings. Could we loan you $4 billion”? I said, “I don't need it. I don't want it. And I've been there. I don't want it. But in two seconds, they give me whatever I wanted.”

To the applause of hired extras that day, he said he has “the greatest assets” worth billions, including Trump Tower (725 5th Avenue), the Neuberger Berman building (1290 Avenue of the Americas) and the Trump Building (40 Wall Street) in New York City and the Bank of America building (555 California Street) in San Francisco. “I'm not doing that to brag, because you know what? I don't have to brag. I don't have to, believe it or not,” Trump said. “I'm doing that to say that that's the kind of thinking our country needs. We need that thinking. We have the opposite thinking.”

And what is that opposite thinking? “We have losers. We have losers,” Trump said. “We have people that don't have it. We have people that are morally corrupt. We have people that are selling this country down the drain.”

Oh, the bombast, the scapegoating, the self-assurance from the nation’s top confidence man (con man, that is), who, to no surprise, refused to release his tax returns.

This Monday, New York Attorney General Letitia James may begin to seize some of those great assets in order to cover fines of $464 million and counting that he owes (and apparently is not rich enough to pay) after losing his tax fraud case. Some financial and legal experts suggest his best option to secure the necessary bond while he appeals—now that over 30 surety companies that could cover his bond refused—is to declare bankruptcy.

It’s a strategy Trump knows well with six previous bankruptcies, including three Atlantic City casinos buried in debt he couldn’t manage. Yet somehow those bankruptcies failed to register with enough voters when they were assessing the quality of this self-described success story.

But The Washington Post reported Wednesday that Trump is loath to declare bankruptcy this time since it might send the wrong message to voters assessing his business acumen and financial worth. “Even though bankruptcy could alleviate his immediate cash crunch,” the Post noted, “it also carries risks for a candidate who has marketed himself as a winning businessman—and whose greatest appeal to voters, some advisers say, is his financial success.”

In other words, declaring bankruptcy would not be simply a legal and financial strategy to buy him time, it would be a loud and clear message of the bankruptcy of the bill of goods he’s been dishing out all these years. A winner, a top businessman, a multi-billionaire can’t come up with half a billion to avoid financial disaster? Is his penthouse apartment—including the toilet—not really covered in gold? Might some of his followers comprehend, heaven forbid, that he’s been lying to them? Could a few even begin to wonder why they have to keep sending him money to pay his legal bills?

As one of those close to Trump told the Post, “He’d rather have Letitia James show up with the sheriff at 40 Wall and make a huge stink about it than say he’s bankrupt…Bankruptcy doesn’t play well for him, but having her try to take his properties might.”

In a 2017 Economist/Yougov poll, 55 percent of Americans said they believed Trump was a successful businessman, including a third of Democrats. By 2019, in a Politico/Morning Consult poll, that view had changed little, as 54 percent still said they thought he was successful in business, including 85 percent of Republicans.

But after respondents in that same 2019 poll learned that Trump reported more than $1 billion in losses from 1985 to 1994—thanks to an exhaustive investigation by The New York Times armed with Internal Revenue Service documents—the percentage who believed in his business success dropped 11 points to 43 percent.

Exit polls from the GOP primaries have found that roughy a third of Republican voters say they think Trump is not fit to be president if he’s convicted of a crime. For many of us who think a man with 91 felony charges should not be nominated for president, that has made the possibility of trial delays that extend beyond the November election that much more maddening.

But perhaps in the coming weeks, if AG James begins padlocking some buildings or otherwise demonstrating that the so-called billionaire is not such a winner after all, some of the pro-Trump crowd (albeit not the impenetrable cultists) might begin to reset their gaze. Maybe, just maybe, the cries of political persecution will strike a few Republicans and a growing number of independents as the sad whines of a bankrupt man. Because, in America, people like winners—and when the odor of loser grows thicker, the crowds turn away.

If you’re not already, please consider becoming a paid subscriber for just $5 a month or $50 a year. This helps sustain and expand the work of America, America, keep nearly all the content free for everyone and give you full access to the comments sections.