At first blush, the historic criminal indictment of Donald Trump seems relatively straightforward: The former president faces fraud-related charges stemming from paying hush money to a porn actress at the height of the 2016 election to prevent her from going public about their alleged sexual encounter.
However, making the case in court, legal experts told the Miami Herald, will be anything but simple.
“There has never been a case with this set of facts,” said former federal and Watergate prosecutor Jon Sale, a prominent white-collar defense attorney based in South Florida. “Nobody is saying it won’t stand up, they’re just saying it’s untested.”
The basic facts of the case read like a salacious tabloid-like narrative. But the Manhattan District Attorney’s Office appears to face a host of complicated legal challenges in the novel way it has shaped the case around a $130,000 payoff to adult film actress Stormy Daniels.
Trump, 76, who is running for reelection in 2024 and has previously denied in public having an affair with Daniels, pleaded not guilty to the indictment on Tuesday in Manhattan’s criminal court, while a throng of news media and others gathered outside.
The indictment charges Trump with 34 felony counts of falsifying business records in the first degree. The records at the core of the case consist of invoices submitted by his former personal lawyer, Michael Cohen, to the Trump Organization for “legal services” that were actually bills for reimbursement to Cohen for paying off Daniels on Trump’s behalf. Cohen, who is cooperating with the Manhattan DA’s office, submitted the 34 invoices in 2017 to a Trump trust that held his business assets when he was in the White House.
“The payment records, kept and maintained by the Trump Organization, were false New York business records,” according to the Manhattan DA’s statement of facts filed separately from the indictment. The statement says Trump “orchestrated a scheme with others to influence the 2016 presidential election by identifying and purchasing negative information about him to suppress its publication and benefit (his) electoral prospects.
“In order to execute the unlawful scheme, the participants violated election laws and made and caused false entries in business records of various entities in New York,” the statement says. “The participants also took steps that mischaracterized, for tax purposes, the true nature of the payments made in furtherance of the scheme.”
What will jurors think?
Still, Sale and other legal experts told the Herald, that state prosecutors in Manhattan will have to persuade jurors the case is more than just muzzling an embarrassing personal story about an affair with Daniels in 2006 — and make it convincing enough to convict someone who happens to be the former president of the United States.
“The jury will have to find whether it was an attempt to influence the outcome of the election,” Sale told the Herald.
To be clear, the Manhattan DA’s criminal case targeting the twice-impeached Trump has nothing to do with potentially more serious allegations in a trio of other ongoing federal and state investigations revolving around keeping top secret classified documents at his Palm Beach estate, and his roles in inciting the Jan. 6, 2021, insurrection at Capitol Hill and meddling in Georgia’s presidential election results.
For starters, the criminal elements in the new indictment returned by the grand jury in Manhattan’s criminal court are more than five years old and likely to face statute of limitations challenges. Also, federal authorities in New York City had previously declined to pursue the same hush-money charges against Trump when he was a sitting president and even after he left the White House.
Perhaps most significantly, Trump’s lawyers will be able to mount a compelling defense that charging the former president in New York state court with breaking campaign finance laws in a federal election is the wrong place to make a case. Moreover, they will argue that he was a victim of what amounted to extortion in the alleged series of payoffs to Daniels — that he was trying to spare himself, wife Melania and his family personal embarrassment rather than prevent a political scandal that might have derailed his presidential showdown with Democratic challenger Hillary Clinton.
But prosecutors can argue that both the personal and political might well have been at play. In the weeks before the 2016 election, the Trump campaign was deeply concerned about the female vote because he had been caught on tape saying to the host of Access Hollywood that “when you’re a star, they (women) let you do it. You can do anything. … Grab ‘em by the (genitals). You can do anything.”
According to the Manhattan DA’s statement of facts, the Trump campaign was also worried about his alleged affair with a former Playboy model, Karen McDougal, who sold her story rights to the National Enquirer for $150,000 in 2016. The tabloid’s publisher, David Pecker, a Trump ally, bought her story but then didn’t publish it — a dubious journalism practice known as “catch and kill.” That case, however, is unmentioned in the indictment.
As a central part of its strategy, experts say, Trump’s defense team will attack the integrity of Manhattan DA Alvin Bragg’s star witness in the hush-money case: Cohen, a now-disbarred lawyer who had worked for the Trump Organization from 2006 to 2017 and served as his “fixer.” Cohen, in both his own federal criminal case and on cable TV news shows, has admitted that he arranged the payment to Daniels, set up a shell corporation to pass the money to her, and was then reimbursed by Trump, who allegedly logged the checks and related bonuses as “legal expenses” — a bit of business record-keeping that is at the core of the Manhattan DA’s case.
In 2018, federal prosecutors in Manhattan charged Cohen with evading taxes related to his investments in the taxi industry, with lying to Congress and with campaign finance violations related to the hush-money payments. Cohen, who has long since publicly turned on Trump, pleaded guilty and served about a year in prison.
One of Trump’s defense attorneys, Joe Tacopina, has gone on the offensive on TV news shows in the run-up to the Manhattan DA’s indictment, questioning his investigation and motives while attacking Cohen’s credibility as a key witness and claiming Trump was extorted.
At a news conference after Tuesday’s arraignment, Tacopina took a shot at the indictment, saying: “I was surprised there were no facts in there.”
But five years ago, long before Tacopina started representing Trump, he told CNN that the payment to Daniels appeared to be “illegal” and a “potential campaign finance issue.” He told the network that claiming Trump wasn’t aware of the payment “doesn’t pass the straight-face test.”
“Anytime you have a snitch or cooperator, they always have baggage,” Sale said about Cohen. “I’ve never seen a cooperator go on television like he has. He’s on a crusade against Trump, though he’s supposed to be a ‘fact’ witness for the state without an agenda. The defense is going to use his words against him.”
‘Intent to defraud’ a key argument
The Manhattan DA’s case is not only unprecedented because it is charging a former U.S. president for the first time. The case is built upon a New York state law that makes it a crime to falsify business records with an intent to defraud. The statute prohibits “a false entry in the business records of an enterprise.” State prosecutors allege Trump personally signed checks to Cohen as reimbursement for the hush money payment to Daniels and listed them as legal expenses. The law, a misdemeanor, is commonly used in New York state court but has never been applied in a federal election campaign case.
To establish a felony case in this instance, the Manhattan DA’s office also alleges Trump’s “intent to defraud” included intentions to commit a second crime. Although the indictment does not spell out the second crime, legal experts said it boils down to Trump’s concealing a federal election donation to his presidential campaign in the form of hush money to Daniels. The hush money payoff far exceeds the limits on corporate contributions to individual candidates. Moreover, Cohen has said he made the donation on Trump’s behalf through a corporation and then Trump reimbursed him through a series of checks from his business.
“Prosecutors don’t have to show the second crime was committed, only that Trump intended to do it,” said veteran Miami defense attorney Mark Schnapp, a former federal prosecutor in South Florida. He added that state prosecutors also don’t have to prove that Daniels took the hush money or her motives for doing so.
Nonetheless, Schnapp and other legal experts said the Manhattan DA’s case poses risks for state prosecutors because they must grapple with a “labyrinth of interlocking laws” in a novel approach to prosecuting alleged federal campaign violations.
The New York Times recently reported on this Catch-22: If the DA uses a federal election law violation as the second crime, Trump’s lawyers could say that federal law has no place in a state court. And if the DA uses a New York election law violation, the defense could claim that a violation of state law does not apply to a federal election, the 2016 presidential campaign.
Case ‘not going to be a cakewalk’
“Either way, it may make the case more legally difficult to prosecute,” Schnapp said. “This is not going to be a cakewalk.”
Schnapp pointed out that the Manhattan DA, Bragg, said after Trump’s arraignment that he was trying to avoid the Catch-22 trap by deploying a New York law that applies to any election — state or federal. In effect, his office is using state law to make a federal campaign case against Trump, Schnapp said.
Miami attorney Juan-Carlos Planas, a former Republican legislator who opposed Trump in the 2020 presidential election, said that as an ex-state prosecutor himself the Manhattan DA’s office has the “discretion” to file criminal charges against the former president.
Planas, who specializes in election law, said Trump may be a former president but “no one is above the law.”
“Theoretically, if I give anyone $150,000 (in a campaign donation) and it’s undeclared, it’s a crime right there,” Planas told the Herald. “Do I think he has worse things coming to him? Yes, I do, but that doesn’t mean you just let this lie.”
Planas said that the Manhattan DA’s case has inherent challenges, but he argued that all corruption and fraud cases built on paper trails and cooperating witnesses present risks.
“Any indictment of a politician presents challenges,” Planas said. “You don’t have to look any further than certain politicians in Miami-Dade County.”
Trump, of course, is not just any politician.
Sale, who as a young lawyer served on the Watergate special prosecutor’s team when then-President Richard Nixon resigned, said that while the nation is bitterly divided over Trump, it is no time to gloat.
“It’s a very sad and solemn day that a former president is indicted,” Sale said. “It’s not a day to celebrate. When Nixon resigned, our office was reminded not to celebrate.”
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