Once again, Donald Trump was down and out. This time, he faced dozens of felony charges, a civil conviction for sexual abuse and 34 criminal convictions in a New York business fraud case – not to mention the ongoing political wreckage from his failed attempt to hold onto power after losing to Joe Biden.
In the years after Trump slinked away from Washington in January 2021, he often appeared more likely to call a federal prison home than to live in the White House again.
But now, Trump has again defied the stacked odds. On Wednesday, he won the presidency back, a stunning reversal of fortune in a short time frame – not only returning him to power but perhaps easing his legal troubles and strengthening his financial outlook.
“Look what happened. Is this crazy?” Trump said early Wednesday morning as he addressed supporters in West Palm Beach, Fla. “It’s a political victory that our country has never seen before.”
In many ways, Trump’s comeback is unparalleled in American history; he’ll be the first convicted criminal to win America’s highest office and the first twice-impeached president to return to the White House, as well as the oldest president to take office.
But his triumphant return follows a long pattern in his career and life – a series of seemingly insurmountable, self-inflicted catastrophes followed by shocking rebounds. There were the six corporate bankruptcies, the exposés on faking and flaunting his way through college, the spectacularly failed casinos, and the allegations of sexual misconduct.
Trump overcame bankruptcies that left others with great losses but sometimes resulted in even more riches for him. After surviving multiple low points, he rocketed to stardom on a reality television show that portrayed him as a wildly successful businessman. He eventually took on democracy itself, convincing millions that even when he lost the presidency, he won it.
Now, he’s campaigned his way back into power, earning the votes of millions of Americans.
For Trump, the many failures and comebacks all became part of his brand, making him one of the world’s most famous people, yet perhaps obscuring just how near to ruin he has repeatedly come.
“He’s failing, he’s going bankrupt, but everybody knows who he is, and they think that he is a wheeler and dealer in business,” said Grant Reeher, a professor of political science at Syracuse University’s Maxwell School of Citizenship and Public Affairs. “How many people, before he ran for president, really understood the failures he had as a business person? And now everybody in the world knows who he is. And I think [being elected again] gives him a certain kind of validation.”
Trump’s story is a spectacular roller-coaster of failures and comebacks, built on an overriding principle: a relentless pursuit of power by whatever means he deems necessary.
Trump once explained his ability to overcome any obstacle by citing a book called “The Natural History of the Rich,” quoting the author in his own book, “Trump: Think Like a Billionaire,” as writing, “Almost all successful alpha personalities display a single-minded determination to impose their vision on the world, an irrational belief in unreasonable goals, bordering at times on lunacy.”
Although Trump doesn’t mention it, author Richard Conniff on the same page noted that Trump’s father, Fred Trump Sr., would tell his son “at every conceivable opportunity, ‘You are a killer … You are a king.’”
Grand success, epic failure
Trump was never supposed to be the leader of the family company.
That job was supposed to go to his older brother, Fred Trump Jr. But Fred wanted a career as a TWA pilot instead of running the real estate business. Fred Jr. died of alcoholism-related illnesses, and Trump’s father made Donald president of Trump Management – putting him on a collision course with the federal government, which sued him and his father over allegations that the Trump company discriminated against Blacks and other minorities. When the case was made public, media coverage focused extensively on Trump.
In one swoop, Trump’s resentment against the federal government and the media took hold – as did his emerging playbook for turning a crisis into an opportunity.
He consulted lawyer Roy Cohn, who said Trump should tell the government to “go to hell,” according to Trump’s account, and to fight back with a $100 million countersuit. Trump followed the advice. He eventually signed a settlement that did not admit guilt but prohibited the Trumps from discriminating against minorities, and he always insisted that he beat the feds.
Instead of focusing on his father’s profitable business of providing drab housing to working-class New Yorkers, he began developing projects in Manhattan and casino properties in New Jersey.
So began a cycle of grand successes and epic failures. He trumpeted his developments but lost millions time and again, filing six corporate bankruptcies and allegedly shortchanging some people who worked for him.
Trump once said he was so deeply in debt that an impoverished blind man who sold pencils on Fifth Avenue was worth $900 million more than him – the amount of Trump’s debts.
By 1990, when Trump faced the prospect of personal bankruptcy, along with what he said in a deposition was a demand from his first wife, Ivana, for “a billion dollars” in a divorce settlement, he sought to take control of his elderly father’s estate. While that effort failed amid family infighting, including accusations that Trump was trying to take advantage of his father’s dementia, Trump did benefit time and again from his father’s largesse.
In the spring of 1990, Trump met with a group of bankers whom he collectively owed $3.2 billion. If he defaulted on one loan, many of the banks could demand payment. But instead of it being one of the darkest days in his career, Trump benefited because the bankers decided it would be disastrous for all of them if he failed. Trump was “worth more alive than dead,” an attorney for one of the banks later told The Washington Post, and the group negotiated a deal providing Trump with $65 million to survive.
Meanwhile, an epiphany for Trump that later proved politically valuable came when his associates advised him to rethink the type of casino customers he needed. Instead of relying on big spenders, he was told to cater to working-class people who would board buses and pump quarters into slot machines.
“He walked through the casino, and the low-rollers would stop everything and flocked around him,” said John O’Donnell, the president of Trump Plaza Hotel and Casino from 1987 to 1990. Trump realized “just how much they loved his persona,” even though the casino was there to take their money, said O’Donnell, who wrote a memoir, “Trumped!” that was critical of his former boss.
Still, the businesses continued floundering. The Taj Mahal casino went into bankruptcy in 1991. The next year, the Trump Plaza Hotel and the Castle Casino also went bankrupt.
As Trump navigated those failures, a parade of bankers, contractors and stockholders over the years have said he made millions at their expense. He made clear that what mattered was whether he benefited. “I wasn’t representing the Fifth Avenue banker. . . . I was representing Donald Trump,” he told The Post in a 2016 interview for the biography “Trump Revealed.” “So for myself, they were all good deals.”
By 1995, Trump had recovered enough that he came up with an audacious plan. He created a publicly traded company with the ticker symbol DJT that raised $140 million at $14 a share, and the stock price rose to $35 the following year.
It was a bonanza for Trump but a bust for many investors. The company paid top dollar for two of Trump’s troubled casinos, leaving shareholders with $1.7 billion of his debt, The Post reported. This new company paid Trump millions, but the share price eventually tanked to 17 cents. Shareholders sued Trump, who eventually reached a modest settlement with them.
He analyzed this outlook in a stark passage in his 2004 book, “Trump: Think Like a Billionaire,” in which he applauded narcissists – and made clear that he approvingly saw himself as one.
“Narcissism can be a useful quality if you’re trying to start a business. A narcissist does not hear the naysayers,” he wrote, citing a book titled “The Productive Narcissist.” That book’s author, psychoanalyst Michael Maccoby, told The Post in 2016 that Trump showed a narcissistic pattern of resenting and not listening to others. “History shows this kind of personality, when they are given power and they are puffed up, can become totally abusive and dangerous,” said Maccoby, who died in 2022.
Trump offset his failures with his mastery of showmanship. The portrayal of him as a super-wealthy and successful real estate titan in his starring role on “The Apprentice” provided massive ratings and a financial windfall. More than 215,000 people signed up for the first 16 contestant slots – a grand echo of those busloads of people who had lined up to play slots at Trump’s casinos – and 20 million people watched the first episode. He has said that he made $213 million directly from the show (the New York Times reported that tax returns showed it was actually $197 million) and millions more indirectly.
Trump built upon that success by selling his name to projects around the world, many of which were no-lose propositions in which he put up little or no money and was guaranteed a profit. Meanwhile, he paid little or no federal taxes for years, according to documents he provided to regulatory officials and reported by The Post, reporting by the New York Times, and a congressional inquiry.
Luck or circumstance
Trump had suggested as long ago as 1987 that he might run for president.
He was a political chameleon, changing his party registration seven times. When he finally did run for president in 2015 as a conservative, antiabortion nationalist, he built a campaign around economic anxiety and his charge that Mexico was sending criminals and rapists to the United States. Gone was his support for abortion rights, a wealth tax and other issues that had once led commentators to describe him as liberal or moderate.
Trump overcame many outrageous statements, such as his disparaging Republican Sen. John McCain’s five years as a prisoner of war in Vietnam, and later, The Post’s publishing the “Hollywood Access” recording in which he said that he could do whatever he wanted with women because he was famous. “Grab them by the p—y. You can do anything,” Trump said.
While some Republicans called for him to drop out of the race, Trump stayed in – and stunningly beat Hillary Clinton in November. During that campaign, Trump foreshadowed his narcissistic and authoritarian tone, saying of the nation, “I alone can fix it.”
Trump’s presidency divided the country, as did his often-erratic behavior and claims, such as that covid-19 could be treated by injecting bleach. His repeated false statements or outright lies were well-documented; The Post’s Fact Checker column found that Trump had 30,573 untruths during his presidency, an average of about 21 per day. Many of Trump’s aides resigned or were fired (often via a tweet).
Some wags said that Trump was “Teflon Don,” with controversies failing to stick. But another metaphor might be even more apt: Trump came with controversies baked in, and often it seemed that no new revelation could alter the positive view that many supporters had of him. They liked what was on the Trump menu no matter the list of ingredients.
Time and again, through luck or circumstance, Trump survived: An investigation by special counsel Robert S. Mueller III concluded that Russia sought to help elect him but did not find evidence that Trump conspired with Moscow. While the report did not exonerate Trump, the former president has often claimed it showed that the matter was a “hoax,” which Democrats and numerous analysts have disputed.
Then, after he was impeached in 2019 on charges that he abused his office and obstructed Congress in his effort to pressure Ukraine to dig up dirt on Joe Biden, he was acquitted in 2020 mostly along party lines, with only one Republican, Sen. Mitt Romney of Utah, joining Democrats to support conviction.
By the time Trump fomented the Jan. 6, 2021, insurrection, leading to his second impeachment, it again seemed his political career was over. To this day, he falsely claims he won the 2020 election. But as had happened so often, he was saved by Republicans who had once been critical of him.
Senate Republican Leader Mitch McConnell may have held the power in his hands to stop Trump from becoming president again. The vote to convict was 57-43, with seven Republicans supporting the measure – 10 short of the needed 67 votes, which would have barred Trump from holding public office. During the impeachment trial, McConnell said, “There’s no question, none, that President Trump is practically and morally responsible for provoking the events of the day.”
But in voting for acquittal on grounds that the Senate did not have the constitutional authority to convict a former president – in a trial that was delayed until after Biden’s inauguration – McConnell provided cover for wavering Republicans to do the same.
Trump had yet again survived, and as he had done so many times before, he focused on exerting power to make a comeback.
After he was blamed by many for his party’s worse-than-expected showing in the 2022 midterms, he faced primary challenges in the 2024 race, including from his own vice president, Mike Pence, and others, convinced the public was exhausted with Trump.
He beat them all, and the Never Trump movement mostly fizzled in the GOP. He exiled anyone he perceived as a threat to his power and installed his daughter-in-law Lara Trump as co-chair of the Republican National Committee. His survival after his ear was grazed by a bullet in an attempted assassination this summer underscored his supporters’ belief that he was invincible.
Even as he reestablished his power in the Republican Party, it seemed that legal cases would still doom him. A New York jury found him liable for sexual abuse and defamation in a case brought by E. Jean Carroll. A New York judge ordered Trump to pay $454 million for falsifying financial data to obtain loans at lower interest rates. Trump was convicted of falsifying business records in a hush money case that centered on a $130,000 payment to adult-film star Stormy Daniels; the judge delayed sentencing until after the election.
In addition, Trump has been indicted in federal cases of election interference and mishandling classified material, and in a Georgia racketeering case. All of the cases have been delayed until after the election, but one of them already has the potential to give Trump more power in his second presidency.
In that federal case, special counsel Jack Smith alleged that Trump sought to overturn the 2020 election. The case was weakened when the Supreme Court ruled 6-3, with all three Trump-appointed justices in favor, that a president is immune from prosecution for actions taken while exercising “core constitutional power.” Smith then revised his filing to try to show that Trump’s effort to overturn the election did not involve his official duties.
To Trump, however, the court ruling is a signal that he can do whatever he wants, including ousting Smith.
“We got immunity at the Supreme Court. It’s so easy. I would fire him within two seconds,” Trump said on Hugh Hewitt’s radio show. He is similarly expected to pressure the Justice Department to drop all federal cases against him.
Before Trump left the presidency, he pardoned a number of associates who remained loyal to him and helped try to return him to power, and he has lashed out at former aides who have called him authoritarian and fascist. His new set of aides is unlikely to provide the pushback Trump received during his first term, essentially removing guardrails from the man who holds vast powers, up to the use of nuclear weapons.
Trump has vowed revenge against foes including Rep. Adam Schiff, the California Democrat who led the prosecution in the first impeachment trial, asserting in interviews on Fox News that he and others could be handled by the National Guard or, “if really necessary, by the military,” and saying, “Shifty Schiff and some of the others, yeah, they are to me the enemy from within.”
He has said he sees his indictments as a “badge of honor” and has vowed to “totally obliterate the ‘deep state’” that he says wants to come after his supporters. “I am your retribution,” he said.
In succeeding at his latest comeback, Trump could feel emboldened to target his enemies, said Todd Belt, professor and director of the political management program at George Washington University. “The guardrails come off for a second Trump presidency,” Belt said.
To those who worry that Trump will consolidate his power and use it against his enemies, the Supreme Court’s immunity decision foretells a dangerous new era that may undo American democracy.
“The relationship between the President and the people he serves has shifted irrevocably,” Justice Sonia Sotomayor said in her dissent in the case. “In every use of official power, the President is now a king above the law.”