Why New York’s hush money case against Donald Trump is viewed as risky

By Tierney Sneed

The case that Manhattan prosecutors have brought against former President Donald Trump for allegedly falsifying business records to disguise hush money payments related to the 2016 campaign presents novel legal questions that make the prosecution risky — but not impossible — legal experts say.

How Manhattan District Attorney Alvin Bragg has laid out his allegations against Trump has attracted skepticism among election law scholars and white-collar defense attorneys. But other experts stress that Bragg has a case that plausibly could end in a guilty verdict and that his legal theories are on solid, albeit untested, ground.

“There are some risks and complications, but I also think there’s a path to conviction,” said Cheryl Bader, a former federal prosecutor who now teaches criminal law and procedure at Fordham University School of Law.

Trump has been charged with 34 counts of falsification of business records, which on its face is a fairly clear-cut allegation. But Bragg has brought the charges — which by themselves, are misdemeanors — as felonies. That will require his team to show that the records were falsified with the intent to conceal or further another crime, yet Tuesday’s court papers provided only a little clarity on how Bragg intends to establish an underlying crime.

Prosecutors are not obligated to show their hand at this stage of the proceedings and there are minimal requirements for what an indictment must say. But given the monumental stakes of the case and how it seems to rest on a novel theory for bringing felony charges, critics say the public would have been better served with more detail.

“I’m not saying there isn’t a hint of what the other crime is,” said Robert Kelner, a defense attorney who specializes in political and election law. “But when you have this weird local statute — in which to prove one crime, you have to show he intended to commit another — you think you’d be very specific.”

The Manhattan hush money prosecution is not the only source of legal jeopardy for the former president and leading 2024 Republican White House candidate. In the coming weeks or months, Trump could be facing criminal charges in Georgia, stemming from a special grand jury investigation into his attempts to undermine the 2020 election. Two federal grand jury investigations being led by special counsel Jack Smith — one focused on the 2020 election subversion allegations and the other concerning White House documents that were taken to Mar-a-Lago — also present significant legal peril for Trump.

“I think the Bragg case is the water pistol unnecessarily preceding the missile-launching F-35 attack piloted by Jack Smith with Merrick Garland as his wingman,” said Ty Cobb, a defense attorney who represented the Trump White House in special counsel Robert Mueller’s Russia investigation.

A simple record-keeping case made more complicated by charging as a felony

The first part of the prosecutors’ case is proving that a series of Trump business records — invoices, checks and general ledger entries — were false, and here the case is straightforward, experts told CNN.

Prosecutors will have physical evidence showing that the checks cut to Michael Cohen were wrongly documented as being for legal fees, when in fact he was allegedly being reimbursed for paying off adult film star Stormy Daniels.

If Bragg was bringing the charge solely as a misdemeanor, he’d need to just show that the records were falsified with the intent to defraud — another fairly easy hurdle to overcome.

But Bragg has brought the 34 counts all as felonies and convincing courts, and ultimately a jury, that this is justified will be the “trickiest part” of the case, according to Paul S. Ryan, an elections law expert who is deputy executive director of the Funders’ Committee for Civic Participation.

To make it a felony, prosecutors will have to point to another potential crime that Trump was trying to further or concealed when he allegedly falsified how the Cohen payments were recorded.

Exactly what this underlying crime was is not specified in the indictment itself, but rather teased in an accompanying statement of facts and in prosecutors’ remarks Tuesday. They describe an “unlawful” scheme to influence the 2016 election by keeping damaging information about Trump from reaching the public.

The district attorney’s theory, as well as the lack of transparency around how Bragg intends to lay it out, is raising concern about whether the case will stand up in court.

Election law expert Rick Hasen told CNN it was “far from a slam dunk.”

“It raises some political questions whether this is the case to bring,” said Hasen, a professor at UCLA School of Law.

The complexity makes it possible that years of litigation lie ahead before the case is fully resolved.

“I see this case as probably ultimately going to the [US] Supreme Court,” said John Coffee, Jr., a white-collar crime professor at Columbia Law School. “You don’t convict an ex-president on a novel legal theory without the Supreme Court looking at it.”

Three routes to a felony, each with their own obstacles

Manhattan prosecutors have teased three different potential underlying crimes that could support the felony charges, but each present their own assortment of novel legal questions.

The first apparent argument is that the business records were falsified to conceal the federal campaign finance crimes committed with the 2016 hush money payments to women alleging extramarital affairs with Trump — crimes to which Cohen pleaded guilty in 2018.

Hasen said he was “skeptical” that a federal campaign finance prosecution could be used to back charges in a state court. Braggs’ defenders have noted that the New York false records statute seems to contemplate the commission or concealment of any crime, and therefore, they argue, it covers federal law violations. Either way, the question could be litigated in the pre-trial phase.

The second potential underlying crime is a state election law Bragg referenced in his press conference: a New York misdemeanor prohibiting two or more people from conspiring to promote a candidacy by unlawful means.

Election law experts are divided on whether that state crime allegation could work as the foundation for the felony. The debate centers on a legal concept known as preemption, which comes into play when the federal law appears to supersede a state law, and whether state prosecutors can go after conduct that is tied to a federal election, i.e. the 2016 presidential campaign.

“Federal election law, generally speaking, preempts state election law when it comes to a governing of federal elections, except there are exceptions whereby certain state election laws can come into play,” said Jerry H. Goldfeder, a veteran election and campaign-finance lawyer at Stroock & Stroock & Lavan. “Apparently [prosecutors] have looked at this seriously enough to conclude they were within their bounds.”

Finally, the charging papers seem to hint that there was an intent to violate New York tax law, suggesting that rationale could be used as the backing for the felony. Under the theory, the way the Cohen reimbursements were structured in the Trump business records would give them different tax treatment than what they would have gotten had they been documented accurately.

“That is state tax crimes,” Ryan Goodman, a New York University Law professor, told CNN’s Erin Burnett Tuesday night. “That is a stronger case because it is insulated from a bunch of the legal challenges, of which there are strong legal challenges to be made to election law crimes.”

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CNN’s Katelyn Polantz, Devan Cole and Fredreka Schouten contributed to this report.