Donald Trump

Based on Wikipedia: Donald Trump

The Art of the Comeback (And the Comeback, And the Comeback)

In 1995, Donald Trump owed more than three billion dollars to banks. They seized his hotels, his yacht, his airline. It was, by any measure, a spectacular failure—the kind that ends careers and becomes a cautionary tale in business school case studies.

Thirty years later, he won his second term as President of the United States.

Whatever else you might say about Donald John Trump, he is perhaps the most consequential American political figure of the twenty-first century—a man who has reshaped one of the country's two major political parties in his own image, survived two impeachments, become the first former president convicted of a felony, and somehow turned each catastrophe into fuel for the next chapter.

The Making of a Manhattan Deal-Maker

Trump was born on June 14, 1946, in Jamaica Hospital in the Queens borough of New York City. His father, Fred Trump, had built a real estate empire constructing middle-class apartment complexes in the outer boroughs—Brooklyn, Queens, Staten Island. The family lived in a twenty-three-room mansion in Jamaica Estates, and Fred paid each of his children roughly twenty thousand dollars a year, which in today's money would be about two hundred sixty-five thousand dollars. By the time Donald was eight years old, adjusted for inflation, he was already a millionaire.

He was, by most accounts, a difficult child.

His father eventually enrolled him in the New York Military Academy, a private boarding school that emphasized sports and, above all, winning. The experience shaped him. So did two mentors he later identified as formative: his father and Norman Vincent Peale, the family's pastor and author of "The Power of Positive Thinking"—a self-help classic that taught readers to visualize success and reject negative thoughts.

Trump attended Fordham University for two years before transferring to the Wharton School at the University of Pennsylvania, where he earned a bachelor's degree in economics in 1968. He later claimed to have been a top student, though he does not appear on the school's honors list. During the Vietnam War, he received an exemption from the draft due to bone spurs in his heels—a diagnosis that would later become a subject of considerable skepticism.

From Rent Collector to Manhattan Mogul

After graduating, Trump joined his father's company, Trump Management, where his primary job was collecting rent and making repairs on the family's outer-borough apartment buildings. He did this for about five years. But Trump was restless. He wanted Manhattan—its glamour, its wealth, its visibility.

His father was content in Brooklyn and Queens. Trump was not.

In 1971, he moved to Manhattan and convinced his father to make him president of the family business, even as Fred remained chairman. Trump began operating under a new umbrella name: the Trump Organization. He also acquired a new mentor—one who would prove at least as influential as his father.

Roy Cohn had been Senator Joseph McCarthy's chief counsel during the anti-communist hearings of the 1950s. By the 1970s, he was a New York fixer with connections to organized crime figures who controlled the construction unions. For thirteen years, Cohn served as Trump's lawyer, mentor, and philosophical guide. The core lesson Cohn taught was simple: life is transactional. Attack, never apologize, declare victory regardless of outcome.

In 1973, the federal government sued the Trumps, alleging their properties had discriminated against Black applicants and tenants. Cohn advised Trump to countersue for one hundred million dollars. The counterclaims were dismissed. The Trumps signed a consent decree agreeing to desegregate. Four years later, they were found in contempt of that decree. Trump, following Cohn's playbook, called it a victory anyway.

Building the Brand

Trump's first major Manhattan project was the renovation of the decrepit Commodore Hotel, next to Grand Central Terminal. The financing came with a four-hundred-million-dollar tax abatement from the city—arranged by his father—and a seventy-million-dollar bank loan guaranteed by his father and the Hyatt hotel chain. When it reopened in 1980 as the Grand Hyatt, Trump was thirty-four years old and had his first taste of the spotlight.

That same year, he secured the rights to build Trump Tower, a mixed-use skyscraper on Fifth Avenue in Midtown Manhattan. It would become his headquarters, his residence, and the physical embodiment of his brand—all gold and mirrors and his name in giant letters.

Through the 1980s, Trump expanded aggressively. He bought the Plaza Hotel. He acquired three casinos in Atlantic City. He purchased an airline, the Eastern Air Lines Shuttle, and renamed it Trump Shuttle. He bought a football team, the New Jersey Generals, in the upstart United States Football League.

He also developed a distinctive approach to business: use other people's money, put your name on everything, and if it fails, make sure the losses belong to someone else.

The Art of the Bankruptcy

By 1990, the whole edifice was wobbling.

Trump's Atlantic City casino, the Taj Mahal, had been financed with six hundred seventy-five million dollars in junk bonds—high-interest debt that proved impossible to service. It filed for bankruptcy protection in 1991. His other two casinos followed in 1992. So did the Plaza Hotel. The Trump Shuttle defaulted on its loans and passed to the banks.

In 1995, Trump defaulted on more than three billion dollars in bank loans. The lenders seized the Plaza and most of his other properties in what one newspaper called a "vast and humiliating restructuring." The lead bank's attorney later explained the banks' decision to let Trump keep operating rather than liquidate everything: "They all agreed that he'd be better alive than dead."

Between 1991 and 2009, Trump filed for Chapter 11 bankruptcy protection six times. Yet he emerged from each collapse with his name intact and his lifestyle largely undiminished. The bankruptcies were corporate, not personal. The losses fell on bondholders, contractors, and banks. Trump kept his penthouses and his golf courses.

This pattern—spectacular leverage, default, restructuring, reinvention—would define his career. By 2018, according to The New York Times, Trump had been involved in more than four thousand lawsuits, liens, and legal filings, many of them for nonpayment against employees, contractors, and even his own attorneys.

The Television Savior

By the early 2000s, Trump's business reputation was in tatters among serious real estate developers and bankers. American banks had largely stopped lending to him. But he had something valuable: fame.

In 2004, NBC launched "The Apprentice," a reality television show in which contestants competed for a job at the Trump Organization. Trump played himself—the billionaire deal-maker, sitting in a boardroom, delivering his signature line: "You're fired."

The show was a hit. More importantly, it rehabilitated Trump's image. To millions of viewers who knew nothing about his bankruptcies or his history of stiffing contractors, he was simply a successful businessman, a symbol of American wealth and confidence. The Trump brand, badly damaged in the 1990s, was suddenly valuable again.

He rode that brand for the next decade, licensing his name to buildings he didn't build, universities that weren't universities, and products ranging from steaks to vodka. The Trump Organization often functioned less as a real estate developer than as a licensing operation—collecting fees for allowing others to put his name on their projects.

The Political Outsider

Trump had flirted with politics for decades, occasionally floating the idea of running for president. In 2015, he finally did it, descending the golden escalator at Trump Tower to announce his candidacy with a speech that included this assessment of Mexican immigrants: "They're bringing drugs. They're bringing crime. They're rapists. And some, I assume, are good people."

NBC and Univision dropped his Miss Universe pageants within days. Mainstream commentators dismissed his campaign as a publicity stunt. Republican Party leaders hoped he would fade quickly.

He did not fade.

Trump understood something his opponents didn't: a large segment of the American electorate was hungry for someone who would break the rules, say the unsayable, and attack the political establishment from both parties. He offered grievance and spectacle. He mocked his opponents with schoolyard nicknames. He dominated news coverage through sheer outrageousness.

In November 2016, he defeated Hillary Clinton to become the forty-fifth President of the United States.

The First Term

Trump's first presidency was marked by a series of aggressive policy moves and constant controversy. He imposed a travel ban on seven majority-Muslim countries. He expanded the wall along the Mexico-United States border and implemented a family separation policy that resulted in thousands of migrant children being taken from their parents. He rolled back environmental regulations and signed the Tax Cuts and Jobs Act, which reduced corporate tax rates and provided tax cuts weighted toward higher earners.

He appointed three justices to the Supreme Court—Neil Gorsuch, Brett Kavanaugh, and Amy Coney Barrett—shifting the court decisively to the right and setting up the eventual overturning of Roe v. Wade, the 1973 decision that had established a constitutional right to abortion.

In foreign policy, Trump withdrew the United States from the Paris climate agreement, the Iran nuclear deal, and the Trans-Pacific Partnership trade agreement. He initiated a trade war with China, imposing tariffs and demanding renegotiation of the terms of the economic relationship.

He was impeached twice.

The first impeachment, in 2019, stemmed from his attempt to pressure Ukraine into investigating Joe Biden and his son Hunter by withholding military aid. The charges were abuse of power and obstruction of Congress. The Senate, controlled by Republicans, acquitted him.

The Pandemic and the Defeat

In early 2020, a novel coronavirus emerged from Wuhan, China, and began spreading around the world. Trump initially downplayed its severity, contradicted public health officials, suggested unproven treatments, and resisted mask mandates. He did sign the CARES Act, a two-trillion-dollar economic relief package, and launched Operation Warp Speed, which accelerated vaccine development. But his public messaging remained erratic, and by Election Day, more than two hundred thirty thousand Americans had died from COVID-19.

Joe Biden defeated Trump in November 2020 by more than seven million popular votes and 306 to 232 in the Electoral College.

Trump refused to concede. He claimed, without evidence, that the election had been stolen through massive fraud. He pressured state officials to "find" votes. He urged the Justice Department to declare the election corrupt. He filed dozens of lawsuits, nearly all of which failed.

On January 6, 2021, as Congress met to certify Biden's victory, Trump held a rally near the White House. He told the crowd to march to the Capitol and "fight like hell." A mob stormed the building, broke windows, assaulted police officers, and sent lawmakers fleeing. Five people died in connection with the attack. Trump was impeached a second time, for incitement of insurrection. The Senate again acquitted him.

Legal Troubles and Convictions

After leaving office, Trump faced an unprecedented cascade of legal problems. In 2023, a civil jury found him liable for sexually abusing the writer E. Jean Carroll in a department store dressing room in the 1990s and then defaming her by denying the assault. He was ordered to pay her eighty-three million dollars.

A New York judge found him liable for business fraud, ruling that he had systematically inflated the value of his assets to obtain favorable loan terms. The penalty was over four hundred fifty million dollars.

Most significantly, in May 2024, a Manhattan jury convicted him on thirty-four felony counts of falsifying business records related to hush money payments to a pornographic film actress before the 2016 election. He became the first former American president to be convicted of a crime.

He was also indicted on federal charges for retaining classified documents after leaving office and for his efforts to overturn the 2020 election results. Both of those cases were ultimately dismissed after he won the 2024 election—the classified documents case on procedural grounds, the election interference case because the Justice Department maintains that sitting presidents cannot be prosecuted.

The Second Coming

Trump ran for president again in 2024, defeating Vice President Kamala Harris to win his second term. He returned to office at seventy-eight years old, the oldest person ever inaugurated as president.

His second term began with a flurry of executive orders and policy changes that went considerably further than his first administration. He initiated mass layoffs of federal workers. He imposed tariffs on nearly all countries at the highest levels since the Great Depression. His administration targeted political opponents and civil society organizations, pursued the mass deportation of immigrants, and issued policies restricting the rights of transgender people.

By the time you are reading this, more than three hundred lawsuits have been filed challenging the legality of various administration actions.

The Reshaping of a Party

Whatever happens next, Trump has already transformed American politics in ways that will outlast his presidency. Since 2015, the Republican Party has been remade in his image. The ideology sometimes called "Trumpism" combines populist economic rhetoric, immigration restrictionism, skepticism of international alliances, and a confrontational political style that treats opponents as enemies to be destroyed rather than adversaries to be debated.

His supporters see him as a fighter who tells uncomfortable truths and challenges corrupt elites. His critics point to his documented history of false statements—The Washington Post counted more than thirty thousand during his first term—his promotion of conspiracy theories, and his willingness to undermine democratic institutions when they produce outcomes he dislikes.

Historians and political scientists have increasingly used terms like "authoritarian" to describe his approach to governance, particularly in his second term. Surveys of scholars have ranked him among the worst presidents in American history.

But rankings by historians are not the same as political power. Trump has proven remarkably resilient. Scandals that would have ended other political careers seemed only to strengthen his bond with his base. His conviction on felony charges did not prevent him from winning a second term. His age did not matter to voters.

The Man Himself

Understanding Trump requires understanding certain consistent patterns across his seventy-plus years of public life.

He has always preferred spectacle to substance, attention to achievement. He learned from Roy Cohn to attack, never apologize, and always declare victory. He treats every interaction as a transaction, every relationship as a deal to be won or lost.

He has demonstrated remarkable skill at branding, self-promotion, and reading the mood of a certain segment of the American public. He has also demonstrated consistent patterns of not paying people what he owes them, of exaggerating his wealth and accomplishments, and of saying things that are demonstrably false.

Whether you see him as a hero or a villain, a truth-teller or a pathological liar, a defender of the forgotten American or a threat to American democracy, probably depends more on what news sources you consume and what values you hold than on any objective assessment of facts.

But the facts themselves are not in serious dispute. He was born wealthy. He went bankrupt multiple times. He became a television star. He won the presidency, lost it, and won it again. He was impeached twice and convicted of thirty-four felonies.

He is, by any measure, one of the most extraordinary figures in American history—extraordinary not in the sense of admirable, but in the sense of defying all normal expectations of what a political career can survive and what a democracy will tolerate.

The story is not over. It may not be over for a long time.