Donald John Trump was born on June 14, 1946, the fourth of five children of Mary Anne MacLeod Trump and her husband, Frederick Christ Trump, Sr. Trump’s mother was born in Scotland and emigrated to the United States in 1930. His father was born in New York City, the son of German immigrants. During Trump’s childhood, the family lived an upscale community of the Queens Borough of New York City known as Jamaica Estates.

Fred Trump owned and operated a successful real estate company called Elizabeth Trump & Son, named after Fred Trump’s mother and himself, which developed properties for middle-class white families in Queens, Brooklyn, and Staten Island. When they were old enough, the three Trump sons—Fred, Jr., Donald, and Robert—worked for the company in construction sites and offices. The Trumps’ daughters, Elizabeth and Maryanne, did not work for the family business. Donald and Robert Trump eventually became involved in their father’s business as adults. Their brother Fred became an airline pilot and died of alcoholism in 1981. Donald Trump cites his brother’s ultimately fatal battle with addiction as the reason he does not drink. Robert Trump died in 2020.

As a child, Trump displayed behavioral difficulties. “He was a pretty rough fellow when he was small,” his father later remembered. In an effort to instill a sense of discipline, his parents enrolled him at age 13 in the New York Military Academy, north of New York City. Trump reported that he enjoyed the drills and lifestyle, but the academy marked the extent of his involvement with the military. He enrolled in Fordham University in New York City and then transferred to the University of Pennsylvania, where he earned a bachelor’s degree in economics through Penn’s Wharton School of Finance and Commerce in 1968.

During the Vietnam War in the late 1960s, when Trump was in his early 20s, he used college and medical deferments (due to a physician’s diagnosis of bone spurs) to avoid being drafted into the armed forces. When the United States instituted a draft lottery system in 1969, an effort to make conscription more random and less dependent on exemptions, Trump’s birthday was number 356 out of 366 in the lottery. He was not called into service.

Trump began his business career while still enrolled in college, investing in Philadelphia real estate. Upon completing his undergraduate education in 1968, he returned to New York and joined his father’s business full time. Public criticism and scandal marked Trump’s early career. In 1973, the US Justice Department accused the Trump company of discriminating against African American would-be renters. Although the company did not admit wrongdoing, it settled the matter by agreeing to rent more apartments to Black tenants.

In the 1970s, Trump helped expand the business, buying properties outside of New York City in locations such as Virginia, Ohio, Nevada, and California. At the same time, he expressed an interest in expanding the company’s real estate operations closer to home, moving from New York’s outer boroughs and into Manhattan, a traditionally more affluent and “high society” area. By the mid-1970s, the now renamed Trump Organization had branched into Manhattan skyscrapers.

Trump’s first big move, in 1976, was to develop the Grand Hyatt Hotel on the grounds of the by-then bankrupt Penn Central Railroad’s Commodore Hotel. Although the Trump Organization did not have enough money to purchase the hotel, Trump used his personal relationship with the Hyatt hotel chain and his father’s political clout (Fred Trump was a prominent member of Brooklyn’s Democratic Party) to negotiate an unusual arrangement with the government of New York City. Trump received a 40-year tax abatement, or a reprieve on paying property taxes on the hotel. Originally worth $4 million per year, the abatement totaled approximately $400 million over 40 years due to inflation in the value of the property and changes in the tax code. He then used the promise of those savings to persuade the Commodore to sell to him and Hyatt to partner with him. “Whatever my friends Fred and Donald want in this town, they get,” New York Mayor Abraham Beame reportedly said of the deal.

In the 1980s, Donald Trump established a reputation as a major real estate developer. He built the 36-story cooperative apartment complex called Trump Plaza as well as Trump Tower on Fifth Avenue, which housed luxury stores and Trump’s own multi-floor residence and company headquarters. He also expanded into the casino business in Atlantic City, New Jersey, building the Trump Plaza Hotel and Casino (originally called Harrah’s at Trump Plaza) and Trump Castle. In 1990, he built the Trump Taj Mahal at a cost of nearly $1 billion—he called it the “eighth wonder of the world.”

Despite these major business operations, the Trump Organization faced severe financial challenges. Trump borrowed significant amounts of money to fund the hotels and casinos. The situation grew so severe in 1990 that Fred Trump, then in his 80s, purchased more than $3 million in casino chips at Trump Castle so the casino could make an interest payment. That purchase was later judged to be an illegal loan, and New Jersey assessed a fine of $65,000. Two Trump-owned companies filed for bankruptcy during this period: the Trump Taj Mahal in 1991 and the Trump Plaza Hotel in 1992. An unflattering biography of Donald Trump, published in 1993, was titled Lost Tycoon and declared that he has become a “public laughingstock” in the wake of his business failures.

In the years that followed, Trump used bankruptcy protection to reconfigure the debts of the many companies that comprised the Trump Organization, successfully making debt payments even as he accumulated more total debt at higher interest rates. As he explained, looking back in 2011: “I’ve used the laws of this country to pare debt.”

He also formed a publicly traded company, Trump Hotels and Casino Resorts, both protecting himself from financial liability and allowing him to sell shares to the general public. He initially owned 56 percent of the stock, giving him a majority and thus total control of the company, which acquired several of the Trump Organization’s properties and companies. In 2004, the company was unable to pay its loans and had failed to turn a profit. It entered bankruptcy protection, and Trump reduced his stock holdings to 27 percent, giving up an active role in the company.

Trump himself blamed the general decline of Atlantic City for his company’s failures, although critics pointed out that his casinos had never done well, even when Atlantic City’s gambling economy had been strong. Efforts to revive the company failed, and it entered bankruptcy again in 2009 and 2014. By the time Trump announced his campaign for president in 2015, his gambling businesses had entirely ceased operation. Shareholders in the company lost their investments, and many vendors and creditors suffered losses, but Trump’s personal financial losses were mitigated by his financial and legal actions.

During his tumultuous business career, Donald Trump retained the public appearance of high-flying success. As his real estate and gambling businesses failed, he succeeded in protecting his brand and shifting into licensing businesses in the United States and abroad. In 2004, the New York Times noted: “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.”

Working with ghostwriters, Trump published a number of how-to and business advice books, including the widely read Trump: The Art of the Deal, first released in 1987. He licensed the “Trump” name to golf courses, hotel resorts, and branded products from steaks to vodka to bottled water. From 1996 to 2015, he was an owner of the Miss USA, Miss Teen USA, and Miss Universe beauty pageants. In 2015, television broadcasters Univision and NBC declined to broadcast the pageants in response to Trump’s racist attacks on Latin American immigrants during his presidential campaign. The next year, Trump announced that he had settled lawsuits with them and sold his stake in the pageants.

Trump’s expansion in the entertainment industry peaked with his role on the hit reality television show The Apprentice, which ran on NBC from 2004 to 2015. Trump played himself on the program, which pitted would-be business leaders against each other in a series of challenges. Trump judged their efforts and whittled down the contestant pool, each week telling one losing contender “You’re fired.” The show and its companion program, Celebrity Apprentice, were widely watched. They helped Trump reach national audiences and confirmed, to many viewers, Trump’s image as a successful and charismatic businessperson who was a straight talker, telling people the hard-to-hear truths. Only when Trump formally announced his presidential campaign with anti-immigrant and racist rhetoric did NBCUniversal formally end his relationship with the program.

Trump’s business interests are bundled into an entity known as the Trump Organization, the descendant of the company founded by his grandmother and father. Trump took over the company in 1971, renamed it in 1973, and bestowed formal leadership of it to his sons Donald, Jr. and Eric in 2017. Unlike a typical business corporation that officially owns its subsidiary parts, the Trump Organization is a collection of approximately 500 individual business entities, all owned principally or solely by Donald Trump himself. None of those constituent parts are publicly traded companies, so they are not required to publicly disclose their financial status or value (as public corporations are). Since Donald Trump, in a departure from recent precedent dating back to President Richard Nixon, never released his personal income tax returns, a complete assessment of the Trump Organization’s finances has proven impossible.

By the time Donald Trump was elected president in November 2016, the Trump Organization owned a vast number of companies, products, and licensing agreements. These holdings included at least a dozen golf resorts in the United States and five in other countries; eight US hotel properties and six abroad; and dozens of other real estate holdings around the world. In August 2016, the New York Times reported that his real estate holdings held at least $650 million in debt. As a candidate, Trump boasted about his high levels of debt and his ability to reduce or eliminate his income tax liability, despite his very high personal net worth. (The exact level of his wealth has been and continues to be debated.) Avoiding taxes, he said during a debate with Hillary Clinton in the fall of 2016, “makes me smart.”

Trump’s businesses were also involved in a large number of lawsuits, both as defendant and plaintiff. The newspaper USA Today reported that, as of 2016, Trump or one of his companies had been involved, in 3,500 legal cases in federal and states courts. Trump was the plaintiff in 1,900, suing someone else; in 1,450, he was the one being sued. The remainder included other types of cases, including bankruptcies.

After his election in 2016, the Trump Organization settled several high-profile cases. Three involved allegations of consumer fraud by the then-defunct Trump University, a for-profit company launched in 2005 that offered classes in real estate and promised to teach the secrets of Trump’s personal success. Trump paid $25 million to settle those suits, without acknowledging wrongdoing. He also closed the charitable non-profit Trump Foundation in the wake of reports that he had not contributed his personal money to the foundation since 2008 but rather used it to distribute money he solicited from others and might have engaged in illegal self-dealing.

Trump’s business career, the idiosyncratic nature of the Trump Organization, and the unknown but substantial levels of personal indebtedness related to his global breadth of assets created an unprecedented situation when he was elected president. Many political observers raised concerns about the potential for conflicts of interest between his businesses and his presidential decisions.

Critics worried that he would inevitably violate the emoluments clause of the US Constitution, which prohibits federal officials from receiving gifts or payments (or anything else of value) from a foreign leader. Any foreign leader, company, or person doing business with a Trump-owned property, those critics charged, would put money into Donald Trump’s pocket. Trump himself rebuffed calls to fully divest himself from his businesses, declaring that he would instead give day-to-day operations of the Trump Organization to his adult sons. They in turn promised to avoid making new deals with foreign countries. Those moves did little to assuage critics’ concerns about the potential for conflicts of interest.