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Prosecuting Trump for Stormy Daniels money would include hurdles, experts say

Former Trump lawyer Michael Cohen is set to testify before a grand jury on Monday, another sign the long-running probe is nearly complete

Former Trump lawyer Michael Cohen arrived to testify before a grand jury on March 13 in the probe into Donald Trump’s 2016 payment to Stormy Daniels. (Video: Shayna Jacobs/The Washington Post)
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NEW YORK — Manhattan District Attorney Alvin Bragg’s investigation into Donald Trump’s payment to an alleged mistress in 2016 appears to be wrapping up, but legal experts say it remains unclear what a criminal case against the former president would look like.

The district attorney could seek charges in coming days or weeks from a grand jury that heard testimony Monday afternoon from Michael Cohen, a former Trump confidant, who spent about three hours there and is expected to resume on Wednesday.

Cohen paid $130,000 to adult-film actress Stormy Daniels in 2016 with the goal of keeping her from publicly claiming she had an affair with Trump years earlier. Bragg (D) is examining whether Trump broke campaign finance laws by using what appeared to be routine legal fees to reimburse Cohen the money he paid to Daniels. Trump denies the affair and maintains that Daniels was an opportunist shaking him down because of his stature and his vulnerability as a presidential candidate.

If Bragg seeks to charge the former president — a move that appears likely based on his recent invitation to Trump to appear before a grand jury — he will face several potential hurdles, legal analysts say. It would be unusual for a state prosecutor to use an alleged violation of a federal law, rather than of a state campaign finance law, as grounds to elevate a false-paperwork case from a misdemeanor to a felony. But it would also be unusual to prosecute a presidential candidate for violating state — as opposed to federal — campaign finance law.

“If there’s an indictment, I look forward to seeing how DA Bragg has crafted his allegations,” said Jerry H. Goldfeder, a veteran election lawyer based in New York. “What appears to be untested is a state prosecutor hanging his hat on a state-law crime to prosecute a federal candidate.”

Either way, Bragg probably would have to rely at least somewhat on testimony from Cohen, an avowed Trump critic who served time in prison for the Stormy Daniels payments, tax evasion and lying to Congress about plans to build a Trump property in Russia. Trump’s defense lawyers would be likely to use those facts to undermine Cohen’s credibility before a jury.

Outside the city building where Cohen testified Monday, he told reporters that his participation in the case was not about “revenge" for him. Rather, he said, Trump should be “held accountable for his dirty deeds.”

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No former president has ever been indicted for a crime, though many political candidates and other officeholders have been charged and convicted of crimes — and for some it has not derailed their political careers. Trump, who lost his bid for reelection in 2020, is seeking the White House again in 2024.

Bragg has given Trump until Thursday to say whether he wants to appear in front of the grand jury — an opportunity available to targets of an investigation in state court in New York if that person’s attorney knows about a grand jury and notifies the district attorney that they want to be invited.

Legal experts have said that extending the grand jury invitation to a potential defendant is typically the last thing that happens in a grand jury probe. It is considered very risky for any defendant to testify in a grand jury proceeding.

“Alvin Bragg, through his actions, is clearly signaling that he’s at the one-yard line to indict Trump,” said Karen Friedman-Agnifilo, who served as chief assistant district attorney under Bragg’s predecessor, Cyrus R. Vance Jr. (D).

Under Vance, the Daniels case was tabled and referenced internally by some as the “zombie case,” an apparent reference to its lifeless state. Prosecutors instead brought a tax-fraud case against the Trump Organization, the former president’s family business, which resulted in a conviction in December of the company. Longtime Trump Organization chief financial officer Allen Weisselberg was also indicted and pleaded guilty.

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After the tax indictment was filed, Vance’s team pivoted to investigate whether Trump and his company illegally misled lenders and insurance companies by inflating asset values to obtain better rates, while reducing his tax liability by deflating those values. Neither Vance nor Bragg sought a grand jury indictment on those allegations. But New York Attorney General Letitia James (D) filed a $250 million civil lawsuit last year against Trump, his family and the Trump Organization based on them.

Any charges that Bragg may seek in the Daniels matter would be relatively low-level. He could ask for an indictment on a felony charge of falsifying business records, which requires allegedly erroneous paperwork to have been created in the course of covering up or committing another crime.

Trump is separately under criminal investigation by the Justice Department for his handling of highly classified material at Mar-a-Lago, his Florida home and private club, after leaving the White House; and by the Justice Department and the district attorney in Fulton County, Ga., over his efforts to block President Biden’s 2020 election victory.

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In the New York investigation, Cohen’s attorney, Lanny Davis, said the investigation of his client’s payments to Daniels by Trump’s own Justice Department five years ago would lay the foundation for any case Bragg might choose to bring against the former president.

Documents filed by federal prosecutors in Cohen’s case referenced him paying Daniels at Trump’s direction. Trump was not charged in that case, but his alleged role was established in the court record. The Justice Department has a long-standing policy of not charging a sitting president, and the U.S. attorney’s office in Manhattan did not appear to revisit the case after Trump left office.

Although Cohen’s plea was based on an admission that campaign laws were violated, the issue of whether the payment to Daniels amounted to a donation was never litigated. Trump has said he was the victim of extortion and could argue at trial that the payment to her cannot be construed as a donation.

Prosecutors would also have the burden of proving Trump intended to violate election law, which would probably mean showing Trump was personally knowledgeable about the rules. Election laws are complex, and candidates generally rely on attorneys well-versed in campaign finance matters.

The former president could also use a newly published book by a former prosecutor in Bragg’s office to undercut any indictment related to Daniels. Mark Pomerantz, who quit the district attorney’s office last year in protest of Bragg’s decision not to seek a fraud indictment based on asset valuation, includes in the book internal deliberations about not pursuing charges against Trump related to Daniels.

Joe Tacopina, an attorney for Trump, cited the book in a letter sent to New York City’s Department of Investigation on Friday that accuses Bragg of prosecutorial misconduct and asks for his office to be investigated. The letter argues that the animus Pomerantz says he felt toward Trump, and his extensive criticism of the former president, prove that the district attorney’s investigation is nothing more than “a patently political prosecution, at the unwarranted expense of this city.”