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Why Alvin Bragg’s Hush-Money Case Against Trump Will Be Tricky to Win

The Manhattan district attorney laid out 34 charges of falsifying documents against the former president, but if the past is any guide, there are pitfalls ahead.

Kena Betancur/Getty Images

Donald Trump pleaded not guilty to 34 counts of falsifying business records on Tuesday during an arraignment hearing in Manhattan. The former president, who is now the first in the nation’s history to be indicted for a felony, did not speak during the hearing.

There was much fulminating in the political/media hot-take foundries about the validity of Manhattan District Attorney Alvin Bragg’s prosecution in the weeks leading up to today’s hearing. Despite this, the charging documents are both unsurprising and fairly straightforward in what they describe. Bragg’s office alleged that Trump took part in a two-year scheme to influence the 2016 presidential election by suppressing negative stories about him.

“In order to execute the unlawful scheme, the participants violated election laws and made and caused false entries in the business records of various entities in New York,” Bragg’s office alleged in its statement of facts. “The participants also took steps that mischaracterized, for tax purposes, the true nature of the payments made in furtherance of the scheme.”

The charges stem from Trump’s extramarital affairs with two women—most famously the adult-film actress Stormy Daniels—and his efforts to hide them during the 2016 presidential election. Daniels sold the rights to publish her stories to the National Enquirer tabloid, whose publisher, David Pecker, was a longtime Trump associate and ally. Michael Cohen, Trump’s former legal fixer, arranged the payments and ultimately disbursed $130,000 to Daniels through a shell company. Cohen then sought reimbursement from Trump via the Trump Organization.

“[Trump] directed [Cohen] to delay making a payment to [Daniels] as long as possible,” prosecutors said in the statement of facts. “He instructed [Cohen] that if they could delay the payment until after the election, they could avoid paying altogether, because at that point it would not matter if the story became public. As reflected in emails and text messages between and among [Cohen], [Daniels’s lawyer], and the AMI Editor-in-Chief, [Cohen] attempted to delay making payment as long as possible.”

Cohen’s payments were part of a broader effort to “catch and kill” stories that could harm Trump’s electoral chances during the 2016 campaign. Packer purchased the stories of Daniels and former Playboy Playmate Karen McDougal, who also alleged that she had an affair with Trump. McDougal received $150,000 from the Trump campaign as part of its efforts to suppress her story. Neither woman went public with her account until after the 2016 election. The Enquirer was ultimately sold to a rival tabloid chain in February 2023.

Cohen pleaded guilty to federal campaign-finance violations in 2018 as part of the broader investigation led by special counsel Robert Mueller. At a hearing where he made his plea allocution, Cohen told a federal judge that he had acted “in coordination with and at the direction of a candidate for federal office,” effectively identifying Trump as an unindicted co-conspirator in the scheme. Mueller ultimately declined to bring further charges against the then-sitting president.

The 34 counts of falsifying business records stem from efforts to hide the reimbursements by Cohen, Trump, and Allen Weisselberg, the Trump Organization’s chief financial officer at the time and a longtime Trump confidant. According to prosecutors, Weisselberg and Cohen folded compensation for Cohen’s $130,000 payment to Daniels into other business-related reimbursements. The two men then agreed to double the various payments to a total of $420,000 and categorize them as income. That would allow Cohen to still effectively receive the $130,000 reimbursement after paying taxes on the overall sum.

“[Trump, Weisselberg, and Cohen] then agreed that [Cohen] would be paid the $420,000 through twelve monthly payments of $35,000 over the course of 2017,” prosecutors claimed in the statement of facts. “Each month, [Cohen] was to send an invoice to [Trump] through Trump Organization employees, falsely requesting payment of $35,000 for legal services rendered in a given month of 2017 pursuant to a retainer agreement. At no point did [Cohen] have a retainer agreement with [Trump] or the Trump Organization.”

New York state law treats the crime of falsifying business records differently depending on the circumstances in which it occurred. Falsifying business records in the second degree occurs when a defendant makes a false entry, omits true information, or prevents someone else from making a true entry. This is only considered a class A misdemeanor under the state’s criminal code.

Falsifying business records in the first degree is a more serious crime—and more difficult to establish. To wit, prosecutors must prove the same elements as in the second-degree offense but also show that the defendant’s “intent to defraud includes an intent to commit another crime or to aid or conceal the commission thereof.” In other words, a prosecutor can’t prove a first-degree charge of falsifying business records unless it was done to further another crime. In this case, the district attorney’s office alleges that Trump, Cohen, and Weisselberg fabricated business records to evade both state election laws and state tax laws.

Cohen and Packer reportedly testified before the grand jury in Manhattan in recent months as Bragg sought to build a case against the former president. One person in Trump’s orbit who apparently refused to cooperate with prosecutors was Allen Weisselberg, the former chief financial officer of the Trump Organization and Trump’s longtime financial confidant. Weisselberg pleaded guilty last year to state tax-evasion and fraud-related charges and is currently serving a three-month prison sentence on Rikers Island. He received a lower sentence after testifying against the Trump Organization last year but apparently declined to cooperate against Trump himself.

Charging a presidential candidate for illicit payments related to infidelity isn’t without precedent. In 2011, John Edwards, the Democrats’ 2004 vice presidential nominee and a 2008 presidential candidate, was indicted by a federal grand jury for illegally soliciting roughly $1 million from his campaign donors to cover up an extramarital affair and an illegitimate child who resulted from it. The Justice Department alleged that the money amounted to an in-kind donation to his 2008 presidential campaign and therefore exceeded federal limits on campaign contributions by individuals.

That case also offers a warning of sorts for Bragg and his office. After failing to reach a plea bargain with Edwards, prosecutors lost the case at trial. Jurors found Edwards not guilty on one count, which involved a $200,000 check from one donor the month he dropped out of the 2008 race, and could not reach a verdict on the other charges. The presiding judge declared a mistrial on those counts, and federal prosecutors ultimately declined to retry Edwards on the charges.

Trump was spared some of the usual indignities of the criminal justice process during Tuesday’s arraignment. A 2019 state law declared that mug shots are no longer considered to be public records and banned their distribution in most circumstances. Since mug shots are taken before a conviction, reformers hoped to lessen the stigma surrounding them. Some reports suggested that Trump hoped to use his mug shot for fundraising purposes, but those hopes were dashed when prosecutors chose to forgo it altogether. The former president was also spared the usual “perp walk” in handcuffs in front of the courthouse in Manhattan. Per reports, Trump’s next mandatory in-person appearance related to these charges will be on December 4.

As his motorcade drove toward the courthouse in Manhattan on Tuesday afternoon, Trump expressed his surprise on Truth Social, his personal social media network. “Seems so SURREAL—WOW, they are going to ARREST ME,” he wrote. “Can’t believe this is happening in America. MAGA!” After pleading not guilty, he returned to his Mar-a-Lago residence in Florida, where he will give a speech about the indictment on Tuesday evening. Somewhere in Manhattan, the 12 men and women who one day may serve on his jury could be watching.