Trump hush money case: Legal experts break down our FAQs

Frequently asked questions, and answers from law experts, about what could be a complicated case against the former president.

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Manhattan District Attorney Alvin Bragg gets out of a shiny black vehicle, beside some barricades.
Manhattan District Attorney Alvin Bragg arrives at his office in New York City on Thursday. (Amanda Perobelli/Reuters)

New York prosecutors appear poised to indict former President Donald Trump as they wrap up their investigation of his role in the hush money payment to porn star Stormy Daniels on the eve of the 2016 election.

The grand jury weighing the evidence could reconvene as early as Monday, when it may hear from more witnesses before voting on an unprecedented indictment. If Trump were to be indicted, he would be the first former U.S. president ever to be charged with a crime.

Manhattan District Attorney Alvin Bragg's office is engaged in delicate negotiations with the Secret Service over how to handle the possible indictment and arrest of Trump, who has been railing against Bragg while urging his supporters to protest.

Yahoo News spoke with several legal experts for answers to some frequently asked questions surrounding the potential case.

When did this investigation begin, anyway?

It began nearly five years ago, when federal prosecutors started probing a $130,000 payment made by Trump’s former lawyer and fixer Michael Cohen to Daniels, who said she'd had an affair with Trump nearly 10 years earlier. Trump denies the allegation. The so-called hush money was given to Daniels, who was threatening to go public with her story.

Stormy Daniels speaks in front of a bank of microphones, with a glass-partitioned door behind her.
Stormy Daniels speaks outside federal court in New York in April 2018. (AP Photo/Mary Altaffer, File)

So what’s wrong with that, legally speaking?

Nothing, except that the hush money payment, arranged by Cohen after consulting with Trump, was listed internally within the Trump Organization as a legal expense — a description that Bragg’s prosecutors are expected to charge as illegal under a New York state law prohibiting falsifying business records.

OK, but isn’t that a misdemeanor?

Yes and no. Under New York law, falsifying business records can be considered a misdemeanor — or a felony if it is carried out in connection with a more serious crime.

And what would that be?

Bragg has not said what charges he may or may not be seeking. And grand jury investigations are conducted in secret. But based on public reporting, it appears that Bragg has been investigating whether the payment to Daniels amounted to an illegal campaign contribution, since it was paid out just days before voters headed to the polls to decide the 2016 presidential election. It is not clear, however, whether Bragg would cite it as a violation of federal or state election law.

A police officer with a dog strides through a flowerbed of daffodils.
A police officer with a dog performs a search outside Manhattan Criminal Court on Wednesday. (Amanda Perobelli/Reuters)

So it’s a novel legal theory, then?

Yes. Prosecutors in New York state have never before filed an election law case involving a federal campaign.

“It is relatively untested waters to bump up this crime to a felony on a federal campaign finance violation,” Duncan Levin, criminal defense attorney and former state prosecutor, wrote in an email to Yahoo News.

The waters are so untested that some observers believe, if Trump were to be indicted, the judge assigned to the case could decide to knock it back to a simple misdemeanor. That bump back would be a bit of an embarrassment for Bragg.

Wait, didn’t the feds drop their investigation against Trump?

Yes. The Southern District of New York successfully prosecuted Cohen for, among other things, making illegal federal campaign contributions. But it never pursued a case against Trump. Bragg’s predecessor, Cyrus Vance, twice looked into the payment and did not bring charges. But Bragg revived what was referred to in the DA's office as the "zombie case."

So how is it a felony charge again?

The misdemeanor — the falsification of business records — would be bumped up to a felony if its specific intent was to commit or conceal another crime, Levin explained. The misdemeanor is relatively easy to prove, he said. But the felony requires the extra step of showing that Trump “falsified these business records with the intent to commit another crime or intent to cover up another crime.”

A Trump supporter in a T-shirt marked America First demonstrates outside Mar-a-Lago in Palm Beach, Fla.
A Trump supporter demonstrates outside Mar-a-Lago in Palm Beach, Fla., after the former president said he expected to be arrested on Tuesday. (Ricardo Arduengo/Reuters)

Isn’t Michael Cohen a problematic witness?

Yes. In 2018, Cohen was sentenced to three years in federal prison for orchestrating payments to Daniels and Karen McDougal — a former Playboy model who also said she'd had an affair with Trump — as well as for lying to Congress. He then wrote a memoir, “Disloyal,” about his transition from Trump fixer to foil, and then a follow-up, “Revenge.” In other words, he’s a convicted liar with a documented ax to grind.

“Anytime you're using someone, you know, who is a convicted felon, that's problematic for the government,” Richard Serafini, a former senior prosecutor with the Justice Department’s Criminal Division, told Yahoo News.

“The issue with him is credibility and honesty,” said Robert Sanders, a senior lecturer at the Henry C. Lee College of Criminal Justice at the University of New Haven and a former federal criminal prosecutor. “He's already been convicted of being a perjurer. He's lied in the past in legal proceedings, and he has a singular focus on Trump. That's something that the jury — any jury — is going to have to take into consideration.”

Michael Cohen gets out of a vehicle in Manhattan.
Michael Cohen arrives on March 15 to testify before the grand jury in Manhattan hearing evidence in the hush money case. (Eduardo Munoz/Reuters)

Can the prosecution overcome that?

Sure, if they can corroborate Cohen’s testimony.

“If the prosecution has prepped this individual properly, and they can be credible, juries have no difficulty in federal court saying, 'Yeah, the guy's been a liar for 20 years, but I believe him based on the other corroborating evidence about this other person's intent,'” New York criminal defense lawyer Andrew Bernstein told Yahoo News.

“It's going to be a battle to corroborate whatever he says if they don't have these smoking gun communications. Do I see a world where people find Michael Cohen credible? I absolutely do. Do I see a world in which they shred his credibility apart? Certainly. I think it's all going to come down to 'The guy said he lied for 20 years,'” said Bernstein. “'Has he told the truth every single day since he got arrested?'”

What are some of the other challenges to Bragg’s case?

Prosecutors will need to prove that Trump was intending to deceive someone by falsifying the business records, but it's less clear who that someone actually is, Levin said.

“It might be the taxation authorities, or auditors looking at the Trump Organization books,” he said.

There’s also the issue of intent, which can be difficult to prove, particularly in a white-collar case. “At the end of the day, you have to prove intent,” Bernstein said. “And how do you prove what's in someone's head?”

Former President Donald Trump looks warily at the photographer as he leaves the lobby of Trump Tower.
Trump leaves Trump Tower in New York City in August 2022. (David "Dee" Delgado/Reuters)

But what about Trump’s claim that he was the one being extorted by Daniels?

Mark Pomerantz, a former prosecutor in the DA's office, thought that might be the case. According to his book, “People vs. Donald Trump,” published last month, Pomerantz wrote that if Daniels had been extorting Trump, then the money could be considered criminal proceeds and efforts to conceal it could be the underlying crime. (Pomerantz declined to be interviewed for this piece.)

Others, though, don't see how it could be considered extortion.

“That is hard to believe, since Trump never reported anything to the police and structured the payments to hide them as though they were attorney's fees,” Levin said. “What was he hiding if he really was being extorted?”

OK, so what are the chances of a conviction?

If Bragg moves forward with an indictment, legal experts say it's an indication that the DA believes there’s a good chance of convicting Trump.

“If you're gonna drag somebody through this, you think there's a likelihood of conviction,” Serafini said. “I would tend to think that certainly applies in a case like this, with a former president. So my guess is that if they're going to indict, they have a feeling of relative confidence that they can sustain the indictment with a conviction.”

A demonstrator with red, white and blue face paint wearing a fur vest and a fur hat decorated with two antlers, raises his fists in the air and shouts in front of the entrance to Trump Tower.
A demonstrator identifying himself as a Trump supporter in front of Trump Tower on Tuesday. (David "Dee" Delgado/Reuters)

Other legal experts we spoke with are not so sure.

“I think this is going to be a very difficult case to prove,” Bernstein said. “I think anytime you have an intent crime going to trial, it can be very difficult. If Donald Trump doesn't take the stand, someone may be left with: 'We don't have much evidence, so I don't really know what was in his head.'”