Trump beat some of the investigations and lawsuits against him and some proved unfounded, but the sheer volume is remarkable. Any one of those scandals by itself would typically have been enough to derail another politician. Joe Biden’s first bid for the presidency collapsed when he lifted some words from another politician’s speech. George W. Bush came close to losing after the last-minute revelation of a long-ago drink-driving arrest. Hillary Clinton fell short at least in part because of an FBI investigation into emails that led to no charges.

Not Trump. He has moved from one furore to the next without any of them sinking into the body politic enough to end his career. The unrelenting pace of scandals may in its own way help him by keeping any single one of them from dominating the national conversation and eroding his standing with his base of supporters.

He even turned that mugshot into a marketing tool, selling T-shirts, posters, bumper stickers, coffee mugs and even beverage coolers with the image and the slogan, “NEVER SURRENDER”. And victory next month may yet help him to escape the biggest threat of all – potentially prison.

Nonetheless, the full record stands out.

Making and losing money

Trump got an early start learning how to cut corners. As a high school student at New York Military Academy, he knowingly borrowed a friend’s dress jacket with a dozen medals attached to wear for his yearbook photo, in effect appropriating medals that he did not win himself, according to a new book, Lucky Loser, by Russ Buettner and Susanne Craig of The New York Times.

He likewise cheated to get into college, according to his estranged niece, Mary L. Trump. The future president paid a friend to take the SAT for him, Mary Trump asserted in her book, earning a score that later helped him transfer to Wharton business school at the University of Pennsylvania, a credential he has boasted about ever since. (A spokesperson for Donald Trump has denied this, and the widow of a man with the name cited by Mary Trump as the test-taking friend said that she was confident the assertion was false.)

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After graduating from Pennsylvania in 1968, however, the former military academy cadet had no interest in serving in the real military and risked being sent to fight in Vietnam. He managed to avoid the draft with a diagnosis of bone spurs in his heels – a diagnosis that evidently was obtained as a favour from a podiatrist in New York City who rented his office from Trump’s father, Fred C. Trump. Two daughters of the podiatrist, who died in 2007, have said that he often told them about saving the younger Trump from Vietnam as a courtesy to his landlord.

Freed from military obligations, Trump went into the family business, helping run his father’s empire of rental apartment buildings in the outer boroughs. Even in those early days, he came under suspicion of misconduct. In 1973, the Justice Department sued the Trump family company for racial discrimination in renting apartments. Applications from black applicants were marked C for “coloured”. Trump fought the matter in court but ultimately agreed to a settlement that the Justice Department at the time called “one of the most far-reaching ever negotiated”.

His business career vaulted him to fame, and he had notable successes, perhaps most prominently the rehabilitation of the Commodore Hotel and the construction of Trump Tower. But he often reached further than he was able to deliver. His record in business was pockmarked with plenty of failures.

The Trump Shuttle airline? Failure. His dreams of building a Television City in Manhattan? Failure. A United States Football League franchise? Failure. The Trump Plaza Hotel and Casino, Trump Taj Mahal, Trump’s Castle Casino Resort, Trump Mortgage, Trump Vodka, Trump University, Trump Steaks, GoTrump.com? All failures.

His most spectacular flameouts came in the gambling mecca of Atlantic City, New Jersey, where he overextended himself building or buying three casinos that ultimately cannibalised each other’s clientele as he failed to keep up with enormous debt payments. He filed for bankruptcy for the Taj Mahal in 1991 and then for the other two casinos in 1992. He also filed for bankruptcy in 1992 for the Plaza Hotel.

Even after recovering from that debacle, Trump failed again. His casino company filed for bankruptcy in 2004 and then again in 2009, for his sixth trip into that process. In his various bankruptcies, he was compelled to sell assets, and creditors were forced to write off some of his debt. But Trump has boasted that he still made money in Atlantic City, even after leaving a trail of losses for nearly everyone else involved, including workers who lost jobs.

‘When you’re a star’

For years, Trump’s personal life was full of scandal, too, enough to make him a frequent topic of the gossip columns of the era. He did not mind. There was almost no headline too scandalous for him. “There’s no bad press unless you’re a paedophile,” he said in front of his campaign manager later in life.

After marrying Czech model Ivana Zelnickova in 1977 and fathering three children, Trump began carrying on an affair with a younger model, Marla Maples. He and Ivana fought out their divorce battle in the news media, at one point making the tabloid front pages 11 days running. He even manoeuvred The New York Post into running a banner headline, “Best Sex I’ve Ever Had”, supposedly describing Maples’ assessment of their bedroom life.

While living with Maples, he boasted of infidelity to a reporter during a call when, bizarrely, he impersonated a spokesman for himself and insisted that Trump had “three other girlfriends” in addition to the woman sharing his home. He and Maples later married anyway and had a daughter before divorcing, too.

He met Melania Knauss, a Slovenian model, and married her in 2005. But he was not always faithful to her either, according to other women. Stephanie Clifford, a porn film actor who goes by the name Stormy Daniels, claimed to have had a tryst with Trump in 2006, four months after Melania Trump gave birth to his fifth child.

Karen McDougal, a former Playboy Playmate of the Year, said she had a 10-month fling with Trump around the same time. Michael Cohen, then Trump’s lawyer and self-described fixer, arranged for six-figure payments to be made to both Clifford and McDougal in 2016 to ensure their silence before the presidential election, hush-money that would later come back to haunt Trump.

His view of women and his belief in his right to pursue them with impunity ultimately was put on display before that election anyway. The now-famous “Access Hollywood” tape posted by The Washington Post weeks before the final balloting revealed his belief that he could “do anything” with women because he was famous. “When you’re a star, they let you do it,” he said. “Grab ’em by the pussy. You can do anything.”

While he later dismissed that as mere “locker room banter”, Trump has been a one-man #MeToo magnet, accused by two dozen or so women of sexual misconduct that goes well beyond banter. One said he grabbed her breasts and tried to run his hand up her skirt on a plane. Another said he kissed her while she worked for him, and at least two others said he groped them at the US Open. Perhaps most famously, E. Jean Carroll, a writer, said he raped her in the dressing room of the Bergdorf Goodman department store in Manhattan in the 1990s.

He has consistently denied all charges, suggesting that all of these women, one after the other, simply made it up. “Every woman lied,” he said in 2016. In a couple of instances, he has dismissed the allegations, not by saying that he would never do such a thing but by saying that he would never do such a thing with those particular accusers because of their looks. “She would not have been the chosen one,” he said last month about one of them.

In the only time one of these allegations made it to a verdict in court, a New York jury last year did not establish that he raped Carroll but did unanimously find that he sexually abused and defamed her and ordered him to pay her $US5 million ($7.5 million). Another jury earlier this year found that he continued to defame her and ordered Trump to pay Carroll $US83.3 million. He is appealing against both judgments.

Avoiding taxes

No president in American history has been wealthier than Trump. And no president in the modern era, at least, paid less in federal income taxes in their first year living in the White House.

Tax documents obtained by the Times in 2020 showed that Trump paid only $US750 in federal income taxes in 2016, the year he originally ran for president, and only $US750 again in 2017, the first year of his presidency. In fact, in 11 of the 18 years examined by the Times, Trump paid no income taxes to the federal government whatsoever.

Trump and his accountants have proved to be master manipulators of the tax code, bending it to benefit him in ways that would usually be damaging to a politician. The self-proclaimed billionaire, currently estimated to be worth $US5.5 billion by Forbes magazine, managed year after year to pay less in income taxes than at least half of American taxpayers through creative bookkeeping if not more questionable tactics.

According to a Times investigation in 2018, Trump and his siblings took a real estate empire from his father that banks a few years later would value at nearly $US900 million and, through favourable appraisals, paid taxes on it as if it were worth just $US57 million. Buildings given by Fred Trump to his children were valued low by the Trump family for tax purposes and high for other purposes, turning a potential $US10 million tax bill into a charge of just over $US700,000, the Times reported.

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Unlike every other modern president, Trump refused to voluntarily release his tax forms, going all the way to the Supreme Court in an ultimately futile effort to shield them from public view. But he has made no apology for avoiding taxes where he can. “That makes me smart,” he famously said in 2016.

The tax forms that did eventually become public highlighted the disparity between his public claims of business conquests and his private claims of business setbacks. In the same year that he published The Art of the Deal, his iconic bestseller promoting himself as a masterful business mogul, his core businesses reported $US45 million in losses on his tax returns.

Trump relied heavily on his father’s fortune to assemble his own. While he likes to say that he parlayed a $US1 million loan from his father into his own empire, the Times investigation in 2018 found that his father had begun giving him $US200,000 a year in inflation-adjusted dollars starting at age three, and that over the course of his career, he received $US413 million in today’s dollars from his father’s real estate business. (Trump disputes this.)

The future president was not content to exploit his own inheritance. He got into a legal battle with his own niece and nephew, who accused him of cheating them out of their share of Fred Trump’s estate. Mary Trump and her brother, Fred Trump III, the children of Donald’s late brother, Fred Trump jnr, argued that they were originally supposed to split a 20 per cent share of their grandfather’s estate, worth millions, upon his death. Instead, under a revised will, the two were each offered a one-time payment of $US200,000.

When they sued, the future president retaliated by cutting his niece and nephew out of the family’s medical insurance fund at a time when the younger Fred Trump was using it to pay for care for his severely ill infant son. “I was angry because they sued,” Donald Trump later explained to the Times. Fred and Mary eventually settled but were embittered that their uncle would betray them in what seemed like a bid to find cash to pay his debts.

“He was willing to squeeze his own niece and nephew and manipulate his father’s wishes, all to try and stop his own creditors from collecting the money he legally owed them,” Fred Trump wrote in All in the Family, a memoir published in July. “If that meant screwing his late brother – well, so be it. If it meant raiding the inheritance of his brother’s two children – well, OK.”

Pursuit and punishment

Scandal followed him to the White House, so much so that he called it “the cloud” and complained that it was getting in the way of governing.

The most consuming scandal of his time in office stemmed from the investigation into Russia’s interference in the 2016 election. While US intelligence agencies determined that Russia sought to tip the contest to Trump, the newly sworn-in president refused to believe that and took any inquiry into the matter as an attack on his legitimacy.

Along the way, he escalated the matter by firing James B. Comey, the FBI director leading the investigation into whether his campaign had any ties with the Russians, and then told visiting Russian officials the very next day that doing so had “taken off” what he called “great pressure”. Actually, it did not. Instead, it led to the appointment of Robert Mueller as special counsel.

After nearly two years of investigating, Mueller concluded that the Russians did interfere on Trump’s behalf, and he uncovered a stunning array of contacts between people in the president’s orbit and Russian figures. But Mueller reported that he did not establish any illegal co-ordination between Russia and the campaign and that “the evidence was not sufficient to charge” anyone with criminal conspiracy.

At the same time, he outlined more than 10 instances in which Trump might have committed obstruction of justice by trying to thwart the investigation – including the dismissal of Comey. Mueller said he did not decide if charges were warranted because Justice Department policy precluded prosecution of a sitting president. Trump insisted this amounted to “total exoneration”, although Mueller explicitly said he was not exonerating the president.

The investigation and media attention on what he called “the Russia hoax” embittered Trump, and during his four years in the White House he expanded the use of government power to target perceived enemies in ways not seen since Watergate. While other presidents shied away from giving the impression that they were wielding the authority of their office for political vengeance, Trump was open about going after his adversaries.

Time and again, he publicly pressed his attorneys general – first Jeff Sessions and then William P. Barr – to prosecute Democrats or government officials who angered him. At various times, he called for the prosecution of Biden, Clinton and former president Barack Obama and lashed out when advisers resisted.

He grew particularly obsessed with prosecuting certain people, like former secretary of state John Kerry. Trump was fixated on the former top diplomat for talking with the Iranians with whom Kerry had negotiated a nuclear agreement from which Trump withdrew the United States. In meeting after meeting, Trump repeatedly badgered Barr to charge Kerry, according to a memoir by John R. Bolton, his former national security adviser.

He also sought to use his power to help specific companies he favoured and penalise those that angered him. He told aides to instruct the Justice Department to block the merger of Time Warner with AT&T, which would include the CNN network, one of the biggest thorns in his side. The Justice Department unsuccessfully sought to stop the merger in court, although officials insisted they acted on their own initiative, not at the behest of the White House.

Trump also tried to penalise Amazon, whose founder Jeff Bezos owns The Washington Post, another media irritant, by pressing for increases in US postal rates for the company and by blocking a $US10 billion Pentagon cloud computing contract.

But he monetised the presidency for himself, as his Trump International Hotel in Washington and other properties became magnets for money from people and institutions currying favour, including the governments of Saudi Arabia, Turkey, Kuwait, the United Arab Emirates and the Philippines. Critics took him to court charging him with violating the emoluments clause of the Constitution barring the acceptance of gifts from “any king, prince, or foreign state”, although the Supreme Court threw out legal challenges.

Most notably, Trump sought to use his office to strong-arm another country to deliver dirt on Biden, a political rival. The president suspended military aid to Ukraine and leaned on its president, Volodymyr Zelensky, to “do us a favour” by announcing an investigation into supposed corruption involving Biden and other Democrats.

For that, the House ultimately impeached Trump for abuse of power on a largely party-line vote, making him only the third president ever to be charged with high crimes, although the Senate failed to reach the two-thirds vote necessary for conviction.

Trump made prolific use of his presidential pardon power to help friends and political allies – and particularly figures who he might have had reason to fear would turn against him by talking with prosecutors if faced with prison time. Critics argued that dangling pardons amounted to an attempt to obstruct investigators.

Among others, Trump gave pardons or commutations to Paul Manafort, his onetime campaign chair; Steve Bannon, his former chief strategist; Roger Stone, his friend and political adviser, all of whom had been in the crosshairs of prosecutors looking at Trump. In the final weeks of his presidency, he also used his clemency power to help felons who paid people close to him to lobby for them.

Trump’s presidency ended in violence as a result of his concerted effort to overturn the 2020 election that he lost so that he could hold onto power despite the will of the voters. He filed dozens of lawsuits and pressured state officials, members of Congress, the Justice Department and his own vice president to help reverse his defeat, something no president has ever done before. And when the crowd of supporters he told to march on Congress stormed the Capitol on January 6, 2021, to try to stop the finalisation of Trump’s defeat, he sat in the White House watching on television without trying to stop it for 187 minutes.

The House impeached him again as a result, accusing him of inciting the riot, with 10 Republicans joining Democrats. Never before had a president been impeached a second time. The Senate ultimately acquitted him again, but this time seven Republicans voted for conviction, and several others said they voted no only because he was already out of office by the time of the trial.

‘The real verdict’

The explosive finale of the Trump presidency did not bring an end to the Trump scandals. On the contrary, it opened a new and unprecedented chapter in the epic and still-unresolved struggles between the 45th president and the US law enforcement system.

In the months after he departed the White House, authorities in Washington, New York, Georgia, Florida and Michigan opened investigations that ultimately led them to Trump. Lawsuits also mounted. Trump became a target or defendant in so many courthouses that his post-presidency has become a full-employment act for defence attorneys.

One after another, judges and juries found against Trump, branding him a fraudster, a sexual abuser and, through his real estate firm, a tax cheat. The two verdicts on behalf of E. Jean Carroll have left him on the hook for nearly $US100 million including interest. The tax fraud conviction of the Trump Organisation made him the first president to head a criminal company.

A separate lawsuit brought by the New York state attorney general, Letitia James, went to the heart of Trump’s self-image as a tycoon of Olympian proportions. Trump’s practice of valuing properties according to his needs came back to bite him when a judge found him liable for sweeping business fraud, ruling that he illegally inflated his net worth in securing loans. The judge not only hit him with penalties that could top $US450 million, but he also barred Trump from leading any business in his original home state for three years. Trump is appealing.

While that judgment in itself was a first in presidential history, it barely seemed to register compared with the criminal cases brought against Trump. In what was then a stunning move, the FBI conducted a search of his Mar-a-Lago estate in Florida to find classified documents that Trump took with him when he left the White House and then refused to give back even when subpoenaed.

And then came what might have once been unthinkable – criminal charges against a former president. Trump was indicted not once, not twice, not three times but four times. While other presidents like Ulysses S. Grant, Warren G. Harding, Richard M. Nixon and Bill Clinton were not without their own scandals, none of them were ever charged with felonies.

The first indictment centred on those hush-money payments to Stormy Daniels. Alvin L. Bragg, the district attorney for Manhattan, charged Trump with falsifying business records to cover up the affair and the payments. The second indictment came in a federal court in Florida, where special counsel Jack Smith charged Trump with mishandling classified documents and obstructing authorities trying to retrieve them.

The third and fourth indictments both stemmed from Trump’s efforts to overturn the 2020 election that he lost. Smith brought an election interference case against him in a federal court in Washington, while Fani T. Willis, district attorney of Fulton County, Georgia, brought a racketeering case against Trump for trying to switch Georgia’s electoral votes. The Michigan attorney general, for her part, named Trump an unindicted co-conspirator in her own election case. He has pleaded not guilty to all charges and blamed Democrats for coming after him for partisan reasons.

The drumbeat of hearings and appeals and procedural fights that have followed may have numbed the shock value, but these cases will stand out in those future history books. He has gone to trial on only one of the four indictments so far, Bragg’s hush-money case, and the jury unanimously found him guilty of 34 felony counts. Sentencing has been pushed off until after the election.

The other three cases are in various states of limbo in part because of aggressive and successful defence moves by Trump’s lawyers aimed at delaying or undercutting the charges against him.

The federal election case was thrown off track for months by Trump’s assertion that he had immunity as president. The Supreme Court largely accepted the argument, ruling for the first time in history that presidents have substantial immunity for crimes related to official acts. Now Judge Tanya S. Chutkan must determine whether Trump’s actions in trying to overturn the election to hold onto power constituted official acts, a process that could stretch out for months.

In the end, she may not get a chance. If Trump is elected next month, he could pull the plug on the federal prosecutions, and even the state cases in New York and Georgia may be frozen while he is in office again. He knows that, and he is counting on it.

As he said earlier this year: “The real verdict is going to be November 5, by the people.”

This article originally appeared in The New York Times.

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