‘He could go to jail’: for Donald Trump, election day is also judgment day

Losing an election for the highest office is a crushing blow that no candidate forgets. But when the American electorate delivers its verdict next week, the personal stakes for Donald Trump will be uniquely high. His fate will hover between the presidency and the threat of prison.

If he claims victory, Trump will be the first convicted criminal to win the White House and gain access to the nuclear codes. If he falls short, the 78-year-old faces more humiliating courtroom trials and potentially even time behind bars. It would be the end of a charmed life in which he has somehow always managed to outrun the law and duck accountability.

For Trump, Tuesday is judgment day.

“He branded himself as the guy who gets away with it,” said Gwenda Blair, a Trump biographer, adding that, should he lose, “he is facing a lot of moments of reckoning. He could go to jail. He could end up considerably less wealthy than he is. No matter what happens, and no matter whether he wins or loses, there will be a reckoning over his health. Death, ill health, dementia – those are things even he can’t escape.”

The property developer and reality TV star has spent his career pushing ethical and legal boundaries to the limit, facing countless investigations, court battles and hefty fines. Worthy of a novel, his has been a life of scandal on a gargantuan scale.

In the 1970s Trump and his father were sued by the justice department for racial discrimination after refusing to rent apartments to Black people in predominantly white buildings. His property and casino businesses, including the Taj Mahal and Trump Plaza, filed for bankruptcy several times in the 1990s and early 2000s.

Trump University, a business offering property training courses, faced multiple lawsuits for fraud, misleading marketing and false claims about the quality of its programmes. In 2016 Trump settled for $25m without admitting wrongdoing.

Donald Trump sits in the courtroom during his civil fraud trial in New York City in November 2023. Photograph: Getty Images

The Donald J Trump Foundation, a charitable organisation, was investigated and sued for allegedly using charitable funds for personal and business expenses. Trump eventually agreed to dissolve the foundation with remaining funds going to charity.

Trump and his company were ordered to pay more than $350m in a New York civil fraud trial for artificially inflating his net worth to secure favourable loan terms. He is also known to have paid little to no federal income taxes in specific years which, although technically legal, was seen by some as bordering on unethical.

But Trump became a fixture of the New York tabloids and hosted his own reality TV show, The Apprentice. Blair added: “His early realisation was that if you get famous, if you get large, people will get out of the way. He spent the first part of his career as a real estate developer, making himself seem the embodiment of enormous tycoon-level success even though, in fact, many things he did weren’t successful and his father kept bailing him out.

“But he put across that impression and he rode that fame express that he had created for himself over a remarkable number of obstacles all the way to The Apprentice, which set him up permanently as the image of this unstoppable always-on-top tycoon and people are in awe of that. All of which could be described as branding.”

Trump’s private life is no more savoury. Trump has reportedly cheated on all three of his wives. More than two dozen women have come forward with accusations of sexual misconduct against him, most recently the former model Stacey Williams, who told the Guardian that Trump groped her in 1993 as Jeffrey Epstein watched in what felt like a “twisted game” between the two men.

During the 2016 election campaign, an Access Hollywood tape emerged in which Trump could be heard bragging about grabbing women by their private parts. “When you’re a star, they let you do it,” he said. “Grab ’em by the pussy. You can do anything.” Then last year a jury found Trump liable for sexually abusing the columnist E Jean Carroll in 1996, awarding her $5m.

Trump’s presidency and its aftermath were no less morally compromised. He made more than 30,000 false or misleading claims over four years, according to a count by the Washington Post newspaper, spanning everything from the crowd size at his inauguration to the result of the 2020 election.

Donald Trump attending board meetings in New York City in 1987. Photograph: Joe McNally/Getty Images

He became the first president to be impeached twice, first for withholding military aid to pressure Ukraine’s government to investigate his political opponents, then for instigating a coup on 6 January 2021 following his defeat. He also became the subject of not one but four criminal cases, any one of which would have been enough to scuttle the chances of any other White House hopeful.

In May Trump was found guilty of 34 counts of falsifying business records relating to a hush-money payment to the adult film performer Stormy Daniels, making him the first former president to be convicted of felony crimes. Sentencing is scheduled for 26 November (the judge delayed it from 18 September after the Republican nominee asked that it wait until after the election).

What was billed as the trial of the century has already begun to fade from public consciousness and played a relatively modest role in the election campaign. Jonathan Alter, a presidential biographer who was in court for every day of the trial, recalled: “I’ve covered some big stories over the years but there was nothing like the drama of watching the jury foreperson say, ‘Guilty, guilty, guilty’ 34 times and Donald Trump looking like he was punched in the gut.”

Alter, who describes the experience in his new book, American Reckoning, reflects on how Trump has been able to act with impunity for so long. “It’s a combination of luck, galvanised defiance and the credulousness of a large chunk of the American people,” he said. “Demagoguery works. Playing on people’s fears works. It doesn’t work all the time but we can look throughout human history to political figures and how demagoguery and scapegoating ‘the other’ works.”

Alter, who covered the trial for Washington Monthly magazine, added: “We’ve had plenty of demagogues, scoundrels and conmen in politics below the level of president. Trump has been lucky to escape accountability but the United States has been lucky that we haven’t had something like this before. The founders were very worried about it. They felt we would face something like this for sure.”

The US’s system of checks and balances has been racing to keep up. Trump was charged by the special counsel Jack Smith with conspiring to overturn the results of his election loss to Joe Biden in the run-up to the January 6 riot at the US Capitol. The former president and 18 others were also charged by the Fulton county district attorney, Fani Willis, with taking part in a scheme to overturn his narrow loss in Georgia.

Trump was charged again by Smith with illegally retaining classified documents that included nuclear secrets, taken with him from the White House to his Mar-a-Lago estate in Florida after he left office in January 2021, and then obstructing government demands to give them back.

With a such a caseload, it was widely assumed that Trump would spend this election shuttling between rallies one day and trials the next. But the courtroom campaign never really happened since, true to past form, he found ways to throw sand in the gears of the legal system and put off his moment of reckoning.

Nancy Pelosi presides over the House of Representatives as they conclude the vote to impeach Donald Trump on 13 January 2021. Photograph: Saul Loeb/AFP/Getty Images

Or he simply got lucky. In Georgia, it emerged that Willis had a romantic relationship with the special prosecutor Nathan Wade, prompting demands that she be removed. Smith’s federal election case was thrown off track for months by a supreme court ruling that presidents have immunity for official actions taken in office. The classified documents case was thrown out by Judge Aileen Cannon, a Trump appointee, although Smith is appealing and the charges could be reinstated.

Such delays have made it easier to forget just how much of an outlier Trump is. Past presidential brushes with the law consisted of Ulysses S Grant being fined for speeding his horse-drawn carriage in Washington and Harry Truman receiving a ticket for driving his car too slowly on the Pennsylvania Turnpike in 1953. Richard Nixon resigned before he could be impeached over the Watergate scandal and was subsequently pardoned by his successor, Gerald Ford.

Meanwhile the standard for presidential aspirants has been high. Joe Biden’s first run for the White House fell apart amid allegations that he had plagiarised a speech by Britain’s Labour leader Neil Kinnock. During the 2000 campaign, a last-minute revelation that Republican candidate George W Bush had a drunk driving conviction that he concealed for 24 years generated huge headlines and was seen as a possible gamechanger. Hillary Clinton still blames her 2016 defeat on an FBI investigation into her email server that produced no charges.

Trump, by contrast, once memorably boasted that he could shoot someone on New York’s Fifth Avenue and not lose any votes. He has done everything but yet still finds himself within touching distance of a second presidency.

Indeed, he has repeatedly flipped the script, citing the cases against him as evidence that he is a martyr of sinister deep state forces. In this version it is Democrats, not Trump, who are the threat to democracy. Claiming solidarity with others who feel a sense a grievance, he often says: “They’re not coming after me, they’re coming after you, and I’m just standing in the way.”

The Georgia case produced the indelible image of Trump’s mugshot, with the former president staring defiantly at the camera. Within hours it had been transformed from a badge of shame into a literal badge for sale, along with posters, T-shirts and other merchandise that is still sported by his fans at rallies with slogans such as “Convicted felon” or “Never surrender”.

Donald Trump’s police mugshot. Photograph: Fulton County Sheriff's Office/AFP/Getty Images

John Bolton, a former national security adviser to Trump, said: “For reasons that I don’t understand, every time he gets indicted his poll numbers have gone up. The reason is people have very negative attitudes about Biden and they think he has weaponised the justice system – which I don’t think he’s done – but Trump has convinced people he’s a victim.

“Every time he gets indicted again, he just uses it as more proof that he’s oppressed. It’s ridiculous but he has turned it. Like a good conman, he’s taken a seemingly impossible argument and made it worth a lot to him.”

This judo move, turning the opponent’s weight against them, might explain why Democrats have not emphasised Trump’s criminal record to the degree that might once have been expected.

Early on, the Democratic nominee, Kamala Harris, did shine a light on Trump’s misdemeanours, drawing a contrast with her past as a courtroom prosecutor by stating: “I took on perpetrators of all kinds: predators who abused women, fraudsters who ripped off consumers, cheaters who broke the rules for their own gain. So hear me when I say I know Donald Trump’s type.”

The line drew cheers but was absent from her closing argument in Washington on Tuesday night, which focused instead on likening Trump to a “petty tyrant” who would sow chaos and division. Indeed, some have taken the view that even criminal convictions pale in significance compared with the threat of a would-be fascist.

But Moe Vela, a lawyer and a former senior adviser to Biden when he was vice-president, said he wishes that Trump’s criminal past had been given greater emphasis by the Harris campaign. “I am extremely surprised we have not heard about that more,” he said. “He is a convicted felon. I thought it should have been said more often in the litany of grievances about him because I thought it was like low-hanging fruit.”

Can Trump’s luck hold one more time? He has waged another White House campaign riven with extremism and racism, divisiveness and violent language, earning comparisons with fascists from the past. If elected, he is expected to use all the levers of power at his disposal to squash the outstanding cases against him; last week he boasted that he would fire his nemesis Smith “within two seconds” of becoming president. But if Trump is defeated by Harris, his legal perils will again gather like a dark cloud.

Vela added: “If he loses this election, I pray to God that she does not in any way pardon him. I hope that our judicial system functions effectively and properly in taking all of these cases through to fruition. Some of them may come out where he is not convicted, but if conviction is the result, he should be punished just like anybody else. No one in this country is above the law.”

That point was illustrated by the New York case, in which even a former president stood trial and was held to account. The system worked. Alter reflected: “That was very inspiring, the wisdom of the judge and jury, who took their responsibilities very seriously. It gave me a lump in my throat. It made me realise we’re not done.”