The defendant looked uncomfortable as he stood to testify in the shabby courtroom. Dressed in a dark suit and somber tie, he seemed aged, dimmed, his posture noticeably stooped. The past year had been a massive comedown for the 76-year-old former world leader. For decades, the bombastic onetime showman had danced his way past scores of lawsuits and blustered through a sprawl of scandals. Then he left office and was indicted for tax fraud. As a packed courtroom looked on, he read from a curled sheaf of papers. It seemed as though the once inconceivable was on the verge of coming to pass: The country’s former leader would be convicted and sent to a concrete cell.
The date was October 19, 2012. The man was Silvio Berlusconi, the longtime prime minister of Italy.
Here in the United States, we have never yet witnessed such an event. No commander-in-chief has been charged with a criminal offense, let alone faced prison time. But if Donald Trump loses the election in November, he will forfeit not only a sitting president’s presumptive immunity from prosecution but also the levers of power he has aggressively co-opted for his own protection. Considering the number of crimes he has committed, the time span over which he has committed them, and the range of jurisdictions in which his crimes have taken place, his potential legal exposure is breathtaking. More than a dozen investigations are already under way against him and his associates. Even if only one or two of them result in criminal charges, the proceedings that follow will make the O. J. Simpson trial look like an afternoon in traffic court.
It may seem unlikely that Trump will ever wind up in a criminal court. His entire life, after all, is one long testament to the power of getting away with things, a master class in criminality without consequences, even before he added presidentiality and all its privileges to his arsenal of defenses. As he himself once said, “When you’re a star, they let you do it.” But for all his advantages and all his enablers, including loyalists in the Justice Department and the federal judiciary, Trump now faces a level of legal risk unlike anything in his notoriously checkered past — and well beyond anything faced by any previous president leaving office. To assess the odds that he will end up on trial, and how the proceedings would unfold, I spoke with some of the country’s top prosecutors, defense attorneys, and legal scholars. For the past four years, they have been weighing the case against Trump: the evidence already gathered, the witnesses prepared to testify, the political and constitutional issues involved in prosecuting an ex-president. Once he leaves office, they agree, there is good reason to think Trump will face criminal charges. “It’s going to head toward prosecution, and the litigation is going to be fierce,” says Bennett Gershman, a professor of constitutional law at Pace Law School who served for a decade as a New York State prosecutor.
Here, according to the legal experts, is how Trump could become the first former president in American history to find himself on trial — and perhaps even behind bars.
You might think, given all the crimes Trump has bragged about committing during his time in office, that the primary path to prosecuting him would involve the U.S. Justice Department. If Joe Biden is sworn in as president in January, his attorney general will inherit a mountain of criminal evidence against Trump accumulated by Robert Mueller and a host of inspectors general and congressional oversight committees. If the DOJ’s incoming leadership green-lights an investigation of Trump after being briefed on any sensitive matters contained in the evidence, federal prosecutors will move forward“at the fastest pace they can,” says Mary McCord, the former acting assistant attorney general for national security.
They’ll have plenty of potential charges to choose from. Both Mueller and the Senate Intelligence Committee — a Republican-led panel — have extensively documented how Trump committed obstruction of justice (18 U.S. Code § 73), lied to investigators (18 U.S. Code § 1001), and conspired with Russian intelligence to commit an offense against the United States (18 U.S. Code § 371). All three crimes carry a maximum sentence of five years in prison — per charge. According to legal experts, federal prosecutors could be ready to indict Trump on one or more of these felonies as early as the first quarter of 2021.
But prosecuting Trump for any crimes he committed as president would face two significant and perhaps fatal hurdles. First, on his way out of office, Trump could decide to preemptively pardon himself. “I wouldn’t be surprised if he issues a broad, sweeping pardon for any U.S. citizen who was a subject, a target, or a person of interest of the Mueller investigation,” says Norm Eisen, who served as counsel to House Democrats during Trump’s impeachment. Since scholars are divided on whether a self-pardon would be constitutional, what happens next would depend almost entirely on which judge ruled on the issue. “One judge might say, ‘Sorry, presidential pardons is something the Constitution grants exclusively to the president, so I’m going to dismiss this,’ ” says Gershman. “Another judge might say, ‘No, the president can’t pardon himself.’ ” Either way, the case would almost certainly wind up getting litigated all the way to the Supreme Court, perhaps more than once, causing a long delay.
Even if the courts ultimately ruled a self-pardon unconstitutional, another big hurdle would remain: Trump’s claims that “executive privilege” bars prosecutors from obtaining evidence of presidential misconduct. The provision has traditionally been limited to shielding discussions between presidents and their advisers from external scrutiny. But Trump has attempted to expand the protection to include pretty much anything that he or anyone in the executive branch has ever done. William Consovoy, one of Trump’s lawyers, famously argued in federal court that even if Trump gunned someone down in the street while he was president, he could not be prosecuted for it while in office. Although the courts have repeatedly ruled against such sweeping arguments, Trump will continue to claim immunity from the judicial process after he leaves office — a surefire delaying tactic. “If federal charges were ever brought, it is unlikely that a trial would be scheduled or start anytime in the foreseeable future,” says Timothy W. Hoover, president of the New York State Association of Criminal Defense Lawyers. By the time any federal charges come to trial, Trump is likely to be either senile or dead. Even if he broke the law as president, the experts agree, he may well get away with it.
But federal charges aren’t the likeliest way that The People v. Donald J. Trump will play out. State laws aren’t subject to presidential pardons, and they cover a host of crimes beyond those committed in the White House. When it comes to charging a former president, state attorneys general and county prosecutors can go places a U.S. Attorney can’t.
According to legal experts, the man most likely to drag Trump into court is the district attorney for Manhattan, Cyrus Vance Jr. It’s a surprising scenario, given Vance’s well-deserved reputation as someone who has gone easy on the rich and famous. After taking office in 2010, he sought to reduce Jeffrey Epstein’s status as a sex offender, dropped an investigation into whether Ivanka Trump and Donald Trump Jr. had committed fraud in the marketing of the Trump Soho, and initially decided not to prosecute Harvey Weinstein despite solid evidence of his sex crimes. “He has a reputation for being particularly cautious when it comes to going after rich people, because he knows that those are the ones who can afford the really formidable law firms,” says Victoria Bassetti, a fellow at the Brennan Center for Justice who served on the team of lawyers that oversaw the Senate impeachment trial of Bill Clinton. “And like most prosecutors, Vance is exceptionally protective of his win-loss rate.”
But it was Vance who stepped up when the federal case against Trump faltered. “He’s a politician,” observes Martin Sheil, a former IRS criminal investigator. “He’s got his finger up. He knows which way the wind’s blowing, and he knows the wind in New York is blowing against Trump. It’s in his political interest to join that bandwagon.”
Last year, after U.S. Attorneys in the Southern District dropped their investigation into the hush money that Trump had paid Stormy Daniels, Vance took up the case. Suspecting that l’affaire Stormy might prove to be part of a larger pattern of shady dealings, his office started digging into Trump’s finances. What Vance is investigating, according to court filings, is evidence of “extensive and protracted criminal conduct at the Trump Organization,” potentially involving bank fraud, tax fraud, and insurance fraud. The New York Times has detailed how Trump and his family have long falsified records to avoid taxes, and during testimony before Congress in 2019, Trump’s longtime fixer Michael Cohen stated that Trump had inflated the value of his assets to obtain a bank loan.
Crucially, all of these alleged crimes occurred before Trump took office. That means no claims of executive privilege would apply to any charges Vance might bring, and no presidential pardon could make them go away. A whole slew of potential objections and delays would be ruled out right off the bat. What’s more, the alleged offenses took place less than six years ago, within the statute of limitation for fraud in New York. Vance, in other words, is free to go after Trump not as a crooked president but as a common crook who happened to get elected president. And the fact that he has been pursuing these cases while Trump is president is a sign that he won’t be intimidated by the stature of the office after Trump leaves it.
In writing up an indictment against Trump, Vance’s team could try to string together a laundry list of offenses in hopes of presenting an overwhelming wall of guilt. But that approach, experts warn, can become confusing. “A two- or three-count indictment is easier to explain to a jury,” says Ilene Jaroslaw, a former assistant U.S. Attorney. “If they think the person had criminal intent, it doesn’t matter if it’s two counts or 20 counts, in most cases, because the sentence will be the same.”
There are two main charges that Vance is likely to pursue. The first is falsifying business records (N.Y. Penal Law § 175.10). During Cohen’s trial, federal prosecutors filed a sentencing memorandum that explained how the Trump Organization had mischaracterized hush-money payments as “legal expenses” in its bookkeeping. Under New York law, falsifying records by itself is only a misdemeanor, but if it results in the commission of another crime, it becomes a felony. And false business records frequently lead to another offense: tax fraud (N.Y. Tax Law § 1806).
If Trump cooked his books, observes Sheil, that false information would essentially “flow into the tax returns.” The first crime begets the second, making both the bookkeeper and the tax accountant liable. “Since you have several folks involved,” Sheil says, “you could either bring a conspiracy charge, maximum sentence five years, or you could charge each individual with aiding and abetting the preparation of a false tax return, with a max sentence of three years.”
To build a fraud case against Trump, Vance subpoenaed his financial records. But those records alone won’t be enough: To secure a conviction, Vance will need to convince a jury not only that Trump cheated on his taxes but that he intended to do so. “If you just have the documents, the defense will say that defendant didn’t have criminal intent,” Jaroslaw explains. “I call it the ‘I’m an idiot’ defense: ‘I made a mistake. I didn’t mean to do anything.’ ” Unfortunately for Trump, both Cohen and his longtime accountant, Allen Weisselberg, have already signaled their willingness to cooperate with prosecutors. “What’s great about having an accountant in the witness stand is that they can tell you about the conversation they had with the client,” Jaroslaw says.
Through appeals, Trump has managed to drag out the battle over his tax returns. The case has gone all the way to the Supreme Court, back down to the district court, and back up to the appeals court. But Trump has lost at every stage, and it appears that his appeals could be exhausted this fall. Once Vance gets the tax returns, Eisen estimates, he could be ready to indict Trump as early as the second quarter of 2021.
Sheil, for one, believes Vance may already have Trump’s financial records. It’s routine procedure, he notes, for criminal tax investigators working with the Manhattan DA to obtain personal and business tax returns that are material to their inquiry. But issuing a subpoena to Trump’s accountants may have been a way to signal to them that they could face criminal charges themselves unless they cooperate in the investigation.
Once indicted, Trump would be arraigned at New York Criminal Court, a towering Art Deco building at 100 Centre Street. Since a former president with a Secret Service detail can hardly slip away unnoticed, he would likely not be required to post bail or forfeit his passport while awaiting trial. His legal team, of course, would do everything it could to draw out the proceedings. Filing appeals has always been just another day at the office for Trump, who, by some estimates, has faced more than 4,000 lawsuits during the course of his career. But this time, his legal liability would extend to numerous other state and local jurisdictions, which will also be building cases against him. “There’s like 1,037 other things where, if anybody put what he did under a microscope, they would probably find an enormous amount of financial improprieties,” says Scott Shapiro, director of the Center for Law and Philosophy at Yale University.
Even accounting for legal delays, many experts predict that Trump would go to trial in Manhattan by 2023. The proceedings would take place at the New York State Supreme Court Building. Assuming that the judge was prepared for an endless barrage of motions and objections from Trump’s defense team, the trial might move quite quickly — no longer than a few months, according to some legal observers. And given the convictions that have been handed down against many of Trump’s top advisers, there’s reason to believe that even pro-Trump jurors can be persuaded to convict him. “The evidence was overwhelming,” concluded one MAGA supporter who served on the jury that convicted Paul Manafort, Trump’s former campaign chairman. “I did not want [him] to be guilty. But he was, and no one is above the law.”
Trump’s conviction would seal the greatest downfall in American politics since Richard Nixon. Unlike his associates who were sentenced to prison on federal charges, Trump would not be eligible for a presidential pardon or commutation, even from himself. And while his lawyers would file every appeal they can think of, none of it would spare Trump the indignity of imprisonment. Unlike the federal court system, which often allows prisoners to remain free during the appeals process, state courts tend to waste no time in carrying out punishment. After someone is sentenced in New York City, their next stop is Rikers Island. Once there, as Trump awaited transfer to a state prison, the man who’d treated the presidency like a piggy bank would receive yet another handout at the public expense: a toothbrush and toothpaste, bedding, a towel, and a green plastic cup.
*This article appears in the September 14, 2020, issue of New York Magazine. Subscribe Now!