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Today Is the Day That 50 Years of Grifting Finally Comes to an End

Unless Donald Trump comes up with $454 million, he’s in deep doo-doo. But will his backers ever wake up to reality?

Mary Altafeer/Pool/Getty Images

Have you ever seen a millionaire begging for $5? Me neither. Yet I just watched Donald Trump in an internet video pleading for $5, or $10, or “even $25” from his supporters. That’s a pitch aimed at the people Trump says he loves, “the poorly educated,” who, after all, don’t have much money.

The supposed business genius with the Midas touch looked desperate—a better-dressed version of one of those troubled souls hanging out near traffic intersections hoping to cadge a dollar or two from people waiting for the light to turn green.

After more than 50 years of grifting, Trump has reached the end of his faux-gold brick road. Today, unless Trump somehow produces the cash to cover his bond, Letitia James, the elected New York State attorney general, is going to start grabbing up Trump properties like she landed on his Monopoly squares. That will constitute a kind of end, although Trump’s journey is never finished. He still enjoys solid support from malefactors of power who openly declare their intent to rend our Constitution and end our freedoms. Incredible as it seems, he still could move back into the White House. 

Letitia James as Dorothy 

Think of James as Dorothy, whose little dog Toto pulls back the curtain on the Wizard of Oz. There’s another cinema analogy that’s even more on point, which we’ll get to shortly. But with respect to Oz, the script from that delightful 1939 classic perfectly describes the con job Trump has pulled off for a half-century—until now. Millions of Americans—like the naïvely happy-go-lucky residents of the mythical Emerald City—believe he has godlike powers, so we should fear him and submit to his whims. “Do not arouse the arouse the wrath of the great Oz,” the magical image proclaims to Dorothy and her three friends amid smoke, lights, and loud noises.

Eventually, of course, Toto pulls back the curtain and reveals the traveling snake oil salesman from Kansas, who continues dissembling even when the fraud is uncovered. “Pay no attention to that man behind the curtain,” he says, trying to cover his naked lies before admitting, yes, it’s true. “I’m a humbug,” he acknowledges, a pure fraud through and through. 

Trump will never admit he’s a fraud. His mentor, the notorious lawyer Roy Cohn, taught him never to give an inch. When challenged by law enforcement or anyone else, Cohn taught Trump, attack them as corrupt, dishonest, and jealous enemies of an honest and successful man.

For nearly a month, Trump has been trying everywhere to get someone with deep enough pockets to cover the roughly half-billion dollars he needs to post to prevent the seizure of his bank accounts, real estate, and other assets to pay the judgment against him for persistent fraud.

By his own account, since 2022, he has anticipated that there would be a significant award against him for persistent fraud. He says it’s all a witch hunt, a fact-free assault, ignoring the mountain of evidence from his own files and the fact that every witness he put forth—save one who the judge noted carefully limited his testimony to verifiable facts—lied, dissembled, or posed as an expert despite having no expertise.

Yet, despite knowing what was coming, Trump didn’t prepare or arrange financing to protect his assets. As I’ve written many times, Trump lives a nightmare version of Groundhog Day, trapped in his junior high school years. This case shows how, instead of planning, Trump is like a student who stays up late partying and realizes at dawn that he has only until noon to turn in his semester essay. 

If Trump somehow pulls a half-billion dollars out of someone’s vaults, we face a national security nightmare, whether the source is American or a foreign national or entity. If you doubt that, just remember how Trump says he likes people who put money in his pockets—Russians, Saudis, etc. And remember, he gave away sensitive secrets in a secret meeting in May 2017 with the Russian foreign minister and ambassador, stole a massive trove of national security documents, lied and denied regarding the whereabouts of those documents, and shared secrets with a group of unauthorized Americans and with an equally unauthorized Australian billionaire. 

The Framers of our Constitution anticipated a corruptible president. That’s why they inserted the emoluments clauses, which ban the nation’s chief executive from receiving money from foreign interests or even state governments. Trump flouted those constitutional mandates. But the Framers in 1787 gave no thought to a president in hock, over whom a creditor had leverage. 

Last Thursday, Judge Arthur Engoron expanded the powers of the Trump Organization monitor, Barbara S. Jones, the retired federal judge he appointed last fall to oversee the company. Trump & Co. now must show her all financial records and accounts; must cooperate in tracing money movements. He also said that if Jones needs to, she can spend Trump’s money to do her job right. Engoron advised her to return for even more expansive powers if needed.

At the same time, James has her sights fixed on Seven Springs, the Trump estate in Westchester County that he has claimed was worth as much as $229 million, about 10 times the reasonable number arrived at in one professional appraisal. She’s also planning to put a lien on Trump’s Westchester golf course with its acre-size clubhouse, 18 holes, and a 102-foot artificial waterfall. Trump has claimed that property is worth just $1.3 million, at least for property tax purposes.

Posing as a Multibillionaire 

While Trump desperately tries to find someone foolish or Machiavellian enough to lend him a half-billion dollars or so, he also digs even deeper into the shallow pockets of the poor and working-class people who adore him because they see the myth, not the man. 

At five bucks a pop, Trump would need almost 111 million donations to cover the judgment in his persistent business fraud loss in Manhattan. “The small-dollar donor will be an  initial play, and he will generate some real money from that,” former Republican National Committee Chair Michael Steele told Katy Tur of MSNBC, characterizing Trump’s appeal as “begging.” 

But it’ll be nowhere near what Trump needs to keep running the con that he is a multibillionaire, not a mere centi-millionaire. And even if he gets a last-minute financial lifeline from Jeffrey Yass, the libertarian multibillionaire who owns 7 percent of TikTok owner ByteDance, it doesn’t change the truth that Trump doesn’t have the money to pay New York State. 

The involvement of Yass, just as Congress is debating banning TikTok as a national security threat, shows how flexible Trump’s views are when money is involved. In 2020, he called TikTok a “threat” and banned it, and a second Chinese app, by executive order. A federal court threw out Trump’s order. Then, earlier this month after meeting Yass briefly, Trump adopted the polar opposite position and now opposes banning TikTok.

Trump is already in hock for $92 million to the Chubb Group. This Swiss insurance company put up the bond to delay enforcement of the $83.3 million plus interest that he owes to advice columnist E. Jean Carroll after her second defamation trial. In the first trial, where Carroll won $5 million, Trump became a judicially determined rapist, with the nature of his sexual abuse, the federal judge hearing the case carefully noted, meeting the definition of rape under New York State law.

Where Did the Fortune Go?

When he announced his second run for president nine years ago (he ran briefly in 2000), Trump told us over and over he was worth more than $10 billion. He said he was so rich that he could spend $600 million of his own money on the 2016 campaign. And he said he wouldn’t need to solicit donations. That, he said, assured the American people that he was not the servant of donors slurping up tax dollars from the federal trough.

Now he’s a beggar. And while the small donors won’t have any power over him, anyone who comes up with nine figures of cash certainly will.

As I told CNN last week, Trump has always been desperate for cash because he is not a wealth builder but a cash extractor. For decades, he would get control of an enterprise or create a fictitious business like his fraudulent Trump University and pull cash from it until all that remained was a hollowed-out carcass beside a pile of unpaid bills.

The only time Trump ran a company with publicly traded stock, it went through four rounds of corporate bankruptcy on his watch, even as he extracted at least $83 million for himself in salary, perks, and self-dealing—that is, using company money for his commercial benefit through a different business he controlled. Trump stiffed many casino vendors even though his casino company paid a fortune for his expensive, unremarkable Trump-branded water. 

In some ways, Trump is like the seemingly fabulously wealthy King of Qarth in Game of Thrones. When the Mother of Dragons opens his vault and finds nothing, she orders the King and his spouse locked inside to die. “It’s all a lie,” Jorah Mormont says. 

The money side of Trump’s story isn’t all a lie. He has conned, tricked, and borrowed his way through billions of dollars that slipped through his fingers like water. He is a wealth extractor, not a wealth builder, who made others suffer for his vanity.

He lavishes money on himself with abandon. The money he paid porn star Stormy Daniels, if we believe her account of their less-than-a-minute coupling, works out to spending more than $8 million an hour for sex—and confidentiality. 

Trump ruthlessly cheated everyone else—his niece Mary, investors, governments, vendors, partners, and workers, including lawyers.

Letitia James has now pulled back the curtain on the ungreat and not powerful Trump, who has fooled so many for so long. However, unlike L. Frank Baum’s fictional story, this one doesn’t end with joy but something closer, financially at least, to the awful end of the faux-rich King of Qarth.