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Experts say Trump prosecution far from sure thing

Donald Trump departed Manhattan Criminal Court on Tuesday.ANDREW CABALLERO-REYNOLDS/AFP via Getty Images

The juxtaposition could hardly be starker. In one of the most consequential prosecutions in the country’s history, the alleged criminal acts are based on routine business actions: writing checks, receiving invoices, making entries in a ledger.

As legal observers pored over the 34-count indictment against Donald Trump on Tuesday, some wondered whether alleged conduct, and the legal theories the Manhattan district attorney is relying on to argue that the acts are felonies, will be enough to overcome the considerable challenges of prosecuting the former president.

“As a defense lawyer, there’s a lot to push back against,” said Brad Bailey, a former New York state prosecutor and Republican office-seeker who is now a Boston criminal defense attorney.


Writing on social media, anti-Trump legal pundit Ken White — also a former prosecutor turned defense attorney — wrote, “I’m unimpressed with the indictment and statement of facts.”

Trump pleaded not guilty to all counts of falsifying business records, and his lawyers said they would fight the charges.

Critics pointed to a number of possible weak spots that could complicate the prosecution.

The 34 counts amount to repetitions of small acts designed to conceal reimbursements Trump paid to his fixer Michael Cohen for a hush money payment Cohen made to the former porn star Stormy Daniels, who alleged she’d had a sexual encounter with Trump. (Trump has repeatedly denied having a liaison with Daniels.)

Every month, from February to December 2017, the indictment alleges that Trump or his employees received an invoice from Cohen for fabricated legal services, wrote checks to Cohen for the fake services, and made false entries in an accounting ledger about the payments. Those acts, repeated each month, are the 34 alleged felonies.

Bailey said the indictment’s repetition could show that “this wasn’t just a one-off mistake. It was deliberate, regular, and repeated conduct.”


But he said it also created an opening for a defense to argue that the prosecution is overstating the case. Trump’s attorneys could “tear down” parts of the indictment, arguing that prosecutors were trying to “come up with as many offenses as you possibly can when really there’s no substance to a lot of the alleged offenses,” he said.

Another challenge is the apparent need for Manhattan District Attorney Alvin Bragg’s office to rely on Cohen as a witness. Cohen has already served jail time for his role in the payment to Daniels. He has also been convicted of lying to Congress. But prosecutors likely would not have a case without his testimony, so they will have to persuade jurors to believe him.

“It’s a familiar problem for prosecutors to have to rely on witnesses with credibility problems,” said Ronald Sullivan, director of the Criminal Justice Institute at Harvard Law School, who previously served as special prosecutor in the criminal proceedings against former Missouri governor Eric Greitens stemming from allegations of sexual assault and campaign finance violations.

“You tell jurors, ‘We can’t go pick the perfect witnesses off the witness tree. But we have corroborated what they said and you can rely on it,‘ ” he added.

“But the defense, of course, will have a field day with cross-examination” of Cohen, Sullivan said. “At the end of the day, it will be a credibility contest and the jury will have to decide who to believe.”

Before the case reaches a jury, prosecutors will have to clear other hurdles.


In New York state, falsification of business records is a misdemeanor. But it can be elevated to a felony if the falsification is carried out to commit or conceal “another crime.”

The indictment charges Trump only with the felony version of the records falsification crime. But the document does not specify which other crime elevates the alleged falsifications to that level.

Asked about that apparent omission at a Tuesday press conference, Bragg said, “The indictment doesn’t specify it because the law doesn’t so require.”

But Bragg offered two possibilities.

Since the $130,000 payment to Daniels was made on the eve of the 2016 presidential election and was designed to protect Trump’s candidacy, as the statement of facts alleged, the payment amounted to a contribution to Trump’s presidential campaign. And $130,000 exceeds the cap on contributions by an individual to a political campaign, according to federal election law.

The other legal theory, Bragg said, was that Trump and Cohen had violated New York state law that prohibits “conspir[ing] to promote a candidacy by unlawful means.” The “unlawful means,” Bragg said, included Trump’s and Cohen’s plans to make false statement in business records and to tax authorities about the reimbursement payments to Cohen.

Both theories could present legal challenges. It is unclear if Bragg, a state prosecutor, can rely on federal election law for his case. A former prosecutor in his office, Mark Pomerantz, described that issue as a “gnarly legal question” that had never been tested in New York courts. There was a “substantial risk that felony charges would be dismissed,” he wrote in a new book about his work on the case. (Pomerantz resigned last year over what he described as Bragg’s reluctance to prosecute the Trump case.)


The theory involving New York law would essentially require Bragg to convince a jury that Trump had committed two crimes to secure a conviction in this case: the falsification of business records crime that is actually charged in the indictment, as well as the state election violation described at the press conference.

Bragg said at the Tuesday press conference that his office frequently prosecutes business falsification crimes as both felonies and misdemeanors. Daniel Medwed, a law professor at Northeastern University and a former Legal Aid Society appellate attorney in New York City, said that in the past 15 years, there have been more than two dozen prosecutions of that kind in the judicial jurisdiction that covers Manhattan and the Bronx.

“It is also not unprecedented to tie this type of charge to an alleged campaign finance crime,” he said.

Political risks loom, as well.

“Certainly this case has a heightened potential for a hung jury even in Manhattan, which is heavily anti-Trump,” Martin G. Weinberg, a prominent Boston defense attorney, said following the arraignment. “Because there is the likelihood that at least one juror will viscerally believe that only Donald Trump would be charged with these offenses” for political reasons, Weinberg said.


Sullivan said that Bragg would have weighed all of those issues before choosing to move forward with such high-profile and high-stakes prosecutions.

“If New York were to lose, it would be one of the biggest embarrassments, if not the biggest embarrassment, that office has ever suffered,” he said. “The prosecution will be wise to have a lot of evidence at the ready.”

Mike Damiano can be reached at Travis Andersen can be reached at