Donald John Trump, the fourth of five children of Fred and Mary Trump, was born on June 14, 1946, in New York City’s Queens borough. The family lived in the upscale community of Jamaica Estates, reflecting the success of Fred’s company—Elizabeth Trump & Son, named for his mother and business partner—in developing properties for middle-class families in Queens, Brooklyn, and Staten Island. The three Trump sons—Fred Jr., Donald, and Robert—worked summers and some weekends on construction sites or in offices when they were old enough; the daughters, Elizabeth and Maryanne, were not brought into the business because, Elizabeth would say, “It’s a man’s family.” (Fred Jr., an airline pilot, died in 1981 of alcoholism; Donald cited Fred’s fate to explain why he does not drink or smoke. Robert became an executive in the family business.)
Trump apparently proved a handful for his parents. “He was a pretty rough fellow when he was small,” his father said. Trump’s unbridled energy as a child led his parents to enroll him at 13 in the New York Military Academy, north of New York City, to instill discipline. While Trump reveled in the military drills and trappings, he later avoided service in the Vietnam War with college and medical deferments and a high number in the draft lottery. He started college at Fordham University, but then transferred to the University of Pennsylvania Wharton School for its real estate studies program. Even as a student, Trump invested in Philadelphia real estate. Graduating in 1968 with a bachelor’s degree in economics, Trump returned to New York and the family business.
In 1973, the Trump company settled a racially charged matter: The Justice Department alleged that the Trump company discriminated against African Americans seeking to rent apartments. The Trumps did not admit wrongdoing but agreed to rent more apartments to blacks. They bought property elsewhere, in Virginia, Ohio, Nevada, and California. The younger Trump, however, eyed expansion closer to home—beyond New York’s outer boroughs to Manhattan. By the mid-1970s, he was branching into Manhattan skyscrapers and had renamed the company the Trump Organization. “Not many sons have been able to escape their fathers,” he would tell an interviewer. Trump became company president, his father the chairman. “Donald has a competitive spirit, and I don’t want to compete with him,” Fred Sr. said in the early 1980s.
Trump’s first big move into Manhattan, at age 30, was to develop the Grand Hyatt Hotel from the carcass of a bankrupt Penn Central Railroad’s Commodore Hotel, abutting Grand Central Terminal. It was a complex transaction enabled by Trump’s partnership with the Hyatt hotel chain, his father’s political pull, and a 40-year city tax abatement worth hundreds of millions of dollars over time, the first-ever such tax break for a commercial property in New York. “The project set the pattern for Mr. Trump’s New York career: He used his father’s, and, later his own, extensive political connections, and relied on a huge amount of assistance from the government and taxpayers,” the New York Times wrote in 2016. (Fred Trump was associated with Brooklyn’s Democratic organization.)
Trump followed by building Trump Plaza, an apartment development, and the Trump Tower on Fifth Avenue, which became home to luxury stores as well as to Trump’s multifloor, gold-gilt residence and company headquarters. In the 1980s, he got involved in casinos in Atlantic City, including Trump Plaza (originally known as Harrah’s at Trump Plaza) and Trump Castle. In 1990, he opened his so-called “eighth wonder of the world”—the Trump Taj Mahal. At one point, Trump casinos reportedly employed more than 8,000 people and accounted for nearly one-third of the city’s gambling revenues.
Opening the Trump Taj Mahal, however, was a highly leveraged transaction, with Trump taking on significant debt to open the casino. It was the start of a debt spiral that threatened Trump’s casinos and his broader businesses. Trump’s financial situation got so desperate that Fred Trump bought more than $3 million in casino chips to help his son make an interest payment—a gambit later penalized as an illegal loan. Lenders forced the son to sell assets, including his yacht and the Trump Shuttle airline, and he had to agree to live on a budget. A biography of Trump published in 1993 was unflatteringly called Lost Tycoon; it said Trump was reduced to a “public laughingstock” by financial woes and a personal scandal, his acrimonious divorce from first wife Ivana and marriage to actress Marla Maples.
Through the 1990s, Trump finagled his business finances to make debt payments, in the process borrowing more and at higher rates. He formed a publicly traded company, Trump Hotels and Casino Resorts, which helped protect him from personal liability, but never had a profitable year. By 2004, it was in bankruptcy. Bankers sued, alleging that the Trump name connotes “the failure to pay one’s debts.” Trump blamed the general decline of Atlantic City for dragging down his businesses, but his casinos were losing market share to rivals long before the gambling mecca’s slide. In 2009 and 2014, the casinos were in bankruptcy again; by the time Trump announced for president in June 2015, his gambling empire had collapsed. Yet while shareholders and vendors lost their bets, Trump’s financial maneuvers shielded him personally.
Through it all, Trump kept up the appearance of the high-flying success, protecting his brand as he shifted into new businesses such as licensing deals in the United States and abroad, how-to books like The Art of the Deal, golf and hotel resorts, beauty pageants, and branded products from suits to bottled water. He also expanded into entertainment ventures, including what would become the hit television franchise The Apprentice. From 1996 to 2015, he was an owner of the Miss USA, Miss Teen USA, and Miss Universe pageants. (Univision and NBC in 2015 severed their connection to the pageants over Trump’s remarks at the start of his campaign maligning undocumented immigrants; Trump in 2016 said he settled lawsuits against both companies, then sold his pageant interests.) Even in 2004, as Trump’s casino business was in bankruptcy again, the New York Times noted—in words that would ring true during his campaign years later—“His name has become such a byword for success that even the most humiliating reverses barely dent his reputation. . . . The rules that govern others just don’t apply to Trump.”
The Apprentice, in which Trump played himself, directing contestants in tryouts for jobs and famously telling losers “You’re fired,” ran on NBC from 2004 to 2015. The network planned for a new season even as Trump, the executive producer and star, demurred and spoke of running for president—its brass believing, like many people, that Trump again would not follow through. NBCUniversal ended the relationship only after Trump’s anti-immigrant remarks sparked a furor.
By his election, the Trump Organization had interests—through ownership, management, or brand licenses—with at least a dozen golf resorts in the United States and five internationally, eight hotel properties in the United States and six in foreign countries, and dozens of real estate holdings in the United States and abroad. Other projects were in the works or planned. His holdings continued to be highly leveraged. Before the election, in August 2016, the New York Times reported that Trump’s real estate network in the United States—not counting interests in about 20 other countries—held at least $650 million in debt. “I am the king of debt,” he said during the campaign. “I love debt.”
Trump boasted about his debt because it reduced or eliminated his income-tax liability, which he acknowledged as a candidate. How much debt reduced or eliminated his income-tax liability is unknown, because Trump was the first president since Richard Nixon to refuse to release his tax returns. Avoiding taxes “makes me smart,” he said in one of the presidential debates.
He also bragged about the Trump Organization’s litigiousness. In the United States in 2016, the company was involved in at least 75 lawsuits, USA Today reported, and had been a party to thousands over time. After his election, the company settled some cases, including three that alleged consumer fraud by his defunct Trump University, a for-profit enterprise that started in 2005 and had offered real estate classes claiming to teach Trump’s secrets of success. Trump paid a $25 million settlement without acknowledging wrongdoing. He also folded his charitable Trump Foundation, which had been the subject of Washington Post stories reporting that Trump had not contributed his own money since 2008 but instead gave away money he solicited from others and that he possibly engaged in illegal self-dealing.
After the election, the breadth and global reach of Trump’s assets, along with his companies’ indebtedness to lenders globally, provoked widespread concern about potential conflicts of interest between the businesses and his presidential actions and possible violations of the Constitution’s emoluments clause against receiving payments from foreign nations. Trump rebuffed calls to divest his businesses. Before his inauguration, he announced that sons Donald Jr. and Eric would run the businesses and forswear new deals in foreign countries, and that he would stay out of the business while keeping his stake. Critics worried that this arrangement was insufficient for avoiding conflicts of interest as president.