On a brisk Monday morning in early May, journalists from around the world gathered in a shabby Manhattan courtroom to find out whether Donald Trump would be sent to jail.

For Justice Juan Merchan, the choice was stark: either impose a paltry four-figure fine for what prosecutors alleged were repeated violations of a gag order, or order the incarceration of the man who was once president, and could be again in a few months’ time. Any other criminal defendant would likely be facing some time behind bars after calling witnesses in the case “sleazebags” and suggesting jurors were corrupt.

But Trump is no ordinary defendant. Jailing him would present numerous practical problems — no holding cells in New York were designed to house a secret service detail — and raise potential constitutional issues. And so, the punishment was handed down: $4,000, the maximum financial penalty allowed by law, for a man probably worth billions of dollars.

It was a moment that encapsulated the ways the US justice system has struggled to bring Trump to heel in this, the first-ever criminal trial of a former US president. The hush money case, as it is known, has lasted more than a month, and a verdict could come as soon as next week.

It has not seemed to have had much effect on his support in the polls. Still, the Manhattan district attorney’s case could be the only one against Trump to reach a verdict by the time November’s election comes around.

As a series of colourful characters from the 77-year-old’s past made their way to the 15th floor of the Manhattan courthouse this month to recount his alleged infidelities and improprieties, a Trump-appointed federal judge in Miami kicked the case in which the former president is accused of illegally retaining classified documents into the long grass, setting dates for legal procedures that pushed a trial well beyond polling day.

A day later, a Georgia appeals court agreed to take up Trump’s appeal for the disqualification of Fulton county district attorney Fani Willis, who had a romantic relationship with the lead prosecutor she hired to run the state’s election interference case. The move all but ruled out a trial this year.

Meanwhile, the federal election interference case against Trump has been stalled while the US Supreme Court decides on a monumental question on the scope of presidential immunity. A decision could come anytime between now and when its term ends, typically late June.

These setbacks have pushed the national focus more forcefully on the dilapidated New York County criminal courthouse where Trump was facing 34 felony counts over the bookkeeping of $130,000 paid to buy the silence of Stormy Daniels, who threatened to come forward with allegations of a sexual encounter in the run-up to the 2016 election.

Those hoping for new details about the former president’s conduct were, mostly, disappointed. Even Daniels’ recollection of swatting the real-estate mogul’s backside with a rolled-up magazine before their alleged 2006 tryst had been extensively covered in books, articles and a documentary series before she repeated it on the witness stand.

But for those curious about how the judicial system would hold up in such an unprecedented situation — with such a singular figure as Trump — it has offered some useful lessons.

Trump has a keen understanding of how to navigate the legal system

Although his Truth Social rants may suggest otherwise, Trump turned out to have a canny sense of just how far he could challenge the boundaries of the judicial system. Once Merchan threatened to jail him for further violations of the gag order, the former president largely stuck to more generalised attacks against the substance of the case, and only began assailing an individual prosecutor once it was clear no further witnesses would be called, making it difficult for Merchan to claim he was imperilling the trial.

A courtroom sketch of Justice Juan Merchan
A courtroom sketch of Justice Juan Merchan © Reuters

He managed to attract a stream of political surrogates, including several prominent House Republicans, who travelled to New York and said things about the witnesses that he could not.

“Trump has always been very good at figuring out those workarounds and coming just up to the line,” said Cheryl Bader, an associate professor of law at Fordham University, of his use of elected officials to fill the airwaves with attacks on the case. The defendant seized on the fact that “people have a First Amendment right to criticise the system”, she added.

Astutely, Trump also chose to follow his counsel’s advice and reneged on a promise to take the stand himself — a move that may be personally satisfying but rarely bolsters the case for the defence.

Trump can turn any arena into his campaign HQ

Being forced to sit in an often cold courtroom for eight hours a day and out of the public glare presented a challenge for Trump, who kept complaining he was being prevented from campaigning across the country. But he soon found a way of using the venue to his own advantage.

Donald Trump speaks to the press after a court session, accompanies by lawyer Todd Blanche.
Donald Trump, left, speaks to the press after a court session, accompanied by lawyer Todd Blanche © Getty Images

While there were precious few supporters gathered outside the court, Trump spoke to the nation twice a day via TV cameras set up in the hallway, his comments broadcast live. His aides even brought a portable printer to the courthouse so he could read favourable press and triumphantly present it as evidence of what he calls a “witch hunt” by Democratic prosecutors.

Trump also used his time in New York to campaign more locally, holding rallies or events in New Jersey and the New York City boroughs of Manhattan and the Bronx. He even set up a perfect photo-op for the tabloid press by buying pizzas for fire fighters on his way home one evening.

While he was unable to tour TV studios, some of the US’s biggest on-screen stars came to the courtroom known as ‘Part 59’ to witness events for themselves, including Rachel Maddow, Jeanine Pirro, Anderson Cooper and Jake Tapper. Cooper delighted Trump’s camp by declaring he thought jurors would find star prosecution witness Michael Cohen to not be credible.

The trial did nothing to alienate Trump’s most loyal supporters

The recitation into the record of Trump’s notorious “grab ‘em by the pussy” brag did not stop a coterie of “family values” House Republicans and potential vice-president picks from flocking to Trump’s side in Manhattan, including Speaker Mike Johnson, a devout Christian.

While Trump was early on joined in court by just a handful of aides and his son Eric, the benches reserved for his team were overflowing as the trial entered its latter stages. US senators JD Vance and Tommy Tuberville, and House Republicans Lauren Boebert and Matt Gaetz were among the dozens who filed in to show their support.

Byron Donalds; Doug Burgum; Mike Johnson, Vivek Ramaswamy and Cory Mills outside the court
Republicans flocked to the trial to show their support for Donald Trump. From left: House Republican Byron Donalds; North Dakota governor Doug Burgum; House Speaker Mike Johnson, former presidential candidate Vivek Ramaswamy and Representative Cory Mills © Pool/AFP via Getty Images

The surrogates postured to the press and posted furiously on social media about what they claimed was a miscarriage of justice. At one point, so many Republicans made their way to Manhattan that the party was in danger of temporarily losing its majority on the floor of the House.

Other allies who made the trip included Chuck Zito, the former head of a New York Hell’s Angels chapter turned movie star and stuntman, and law professor Alan Dershowitz.


A jury could decide Trump’s fate as soon as Wednesday. Polls suggest the historic verdict will probably have little influence on who wins the White House, and even a conviction will result in a lengthy appeal process.

George Grasso, a former judge in the same criminal court who has attended the trial, concedes a conviction “won’t necessarily be determinative [to the election]”. But he is in no doubt the facts of the case warranted them being heard by 12 ordinary New Yorkers, and the world.

“Regardless of how this case comes out, this was a justifiable and appropriate case to bring,” he said. “No one is above the law in the United States.”

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