Trump is fighting an uphill battle in his fraud trial. But it could be years before penalties kick in.

1 year ago

NEW YORK — Two months into Donald Trump's civil fraud trial, the case does not seem to be going well for him.

The judge has already ruled that he committed fraud, fined the former president twice for violating a gag order and declared him to be "not credible." Trump and his lawyers, meanwhile, have repeatedly antagonized the judge, attacking him in the press and even disparaging his law clerk.

And now, as Trump's lawyers roll out a defense that at times has looked more like a PR pitch, his New York real estate empire hangs in the balance, with a verdict expected in mid-December.

But even the most punitive verdict is unlikely to immediately devastate Trump's businesses. The case will be subject to lengthy appeals in the New York state courts — and Trump seems to be counting on that appeals process to avoid exorbitant fines and salvage his businesses.

Here are some of the most significant questions remaining as Trump’s trial heads into the home stretch:

What has the judge already decided, and what is the trial about?

The question at the heart of New York Attorney General Tish James’ lawsuit was resolved before the trial even started: Did Trump fraudulently inflate his net worth on financial documents to get favorable treatment from banks and insurers? Justice Arthur Engoron ruled yes.


Engoron also granted one of the most significant punishments sought by James: the cancellation of all of Trump’s business certificates.

An appeals court, however, put that action on hold while it considers Trump’s appeal of Engoron’s ruling.

In the meantime, the ongoing bench trial focuses on other punishments that Trump, his adult sons and the other defendants could face. James is seeking $250 million in penalties, and she wants the judge to permanently bar Trump, Donald Trump Jr. and Eric Trump from serving as officers or directors of any business in New York. She is also seeking to bar Trump and the Trump Organization from acquiring real estate in New York for five years.

What is Trump’s legal defense strategy?

Trump’s lawyers have been presenting his formal defense since mid-November, and so far they’ve relied heavily on expert witnesses, plus one day of testimony from Donald Trump Jr. about the magnificence of Trump properties. Gloating aside, the gist of the defense seems to be that the properties were, in fact, properly valued at the estimates recorded on Trump’s financial statements.

Beyond the testimony, however, Trump’s lawyers appear to be focused on appealing the verdict, just as they have already appealed the pretrial ruling on fraud. They — and Trump — have repeatedly claimed bias on the part of the judge and his principal law clerk, including in a recent request for a mistrial in which they complained about the clerk’s political donations and about the judge’s contributions to his high school alumni newsletter, in which he included links to articles referencing the case. Engoron quickly denied that request, but such arguments about political bias are likely to help form the basis for Trump’s appeal.


Last week, Trump got a sliver of a sign that the appeals courts may indeed be his best hope — or at least a more favorable venue than Engoron’s Manhattan courtroom. In a swift emergency ruling, a New York appellate judge temporarily lifted gag orders that Engoron had placed on Trump and his lawyers.

Is Donald Trump on the hook for the entire $250 million?

It’s up to the judge. Engoron could order that various defendants pay various financial penalties, so it is not necessarily the case that Trump himself will be responsible for paying the full amount. However, Trump is effectively the chief executive of the operation and — according to testimony by Michael Cohen, his former lawyer and fixer — Trump instructed those crafting the financial statements to inflate his net worth. So Engoron would likely deem Trump responsible for most, if not all, of any financial penalty he metes out.

Cohen said Trump didn’t explicitly order him to enter larger numbers on the statements, but he added: “Donald Trump speaks like a mob boss and what he does is he tells you what he wants without specifically telling you. So when he said to me, ‘I'm worth more than five million. I'm actually worth maybe six, maybe seven, could be eight,’ we understood what he wanted.”

Does Trump have enough cash on hand to pay such a penalty without selling assets?

A Trump spokesperson didn’t respond to a question about whether Trump has adequate cash to pay a potential $250 million fine. In a recent interview on MSNBC, Cohen said Trump couldn’t afford such a penalty without offloading some assets. “No, no,” Cohen said. “He’s going to have to sell.”


Would he have to pay right away?

Probably not. If Engoron orders Trump to pay immediately, he may need to pay an appeal bond, money that gets held until after the resolution of an appeal. But the more likely scenario is that when Trump’s lawyers appeal, they can also seek an emergency stay of the payment, thereby delaying the date by which he needs to turn over the money.

Catherine Christian, a former prosecutor with the Manhattan district attorney’s office, predicted the state’s intermediate appeals court would fast-track Trump’s appeal, estimating that it might take a year. Either side could then appeal that ruling to the state’s highest court, known as the New York Court of Appeals. Christian said the only way the matter could then reach the U.S. Supreme Court is if Trump argues that the penalties somehow violate his federal constitutional rights.

What about the cancellation of Trump’s business certificates?

The intermediate appeals court, known as the Appellate Division, has already paused Engoron’s order canceling Trump’s business certificates while it considers Trump’s appeal of Engoron’s pretrial ruling that found Trump had fraudulently inflated his net worth on financial documents.

If the appeals court eventually upholds Engoron’s ruling and lifts the pause on the order, however, that could deliver a significant blow to Trump’s company, potentially removing the certificates of Trump Tower, 40 Wall Street, the Trump International Hotel and the Trump Organization, among other New York entities “controlled or beneficially owned” by Trump. Diana Florence, a former prosecutor with the Manhattan district attorney’s office, compared stripping a company of its business certificate to issuing a death certificate to a person.

“It literally means the company is dead, and once a company is dead, they can’t take their stuff with them,” she said. An executor appointed by the court would dispose of the assets, and once the bills and receivables are sorted out, the rest goes to the owners of the company.

If most of those proceeds go to Trump, he may incur an additional penalty, said Florence. “He’s going to be hit with a whopper of a tax bill.”

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